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  • Best Portable Carbon Monoxide Detector for Travel (2026 Review)

    Wondering if you need a carbon monoxide detector for travel? Hotels and vacation rentals don’t always have working CO alarms, and carbon monoxide poisoning kills travelers every year. Here’s the portable detector we never travel without and why it could save your life.

    Traveling is incredible. You get to explore new places, experience different cultures, and create lasting memories. But there’s one thing most travelers overlook that could literally save their lives.

    It’s not travel insurance. It’s not a first aid kit. It’s something even more fundamental to your safety.

    It’s a portable carbon monoxide detector.

    I know what you’re thinking. Isn’t that being a bit paranoid? Unfortunately, no. After researching the risks and hearing real stories of travelers who didn’t make it home, I never travel without one anymore. And once you read what I’ve learned, you won’t either.

    Quick Answer: Do I Need a CO Detector for Travel?

    Yes. Carbon monoxide poisoning kills travelers every year in hotels, vacation rentals, and Airbnbs worldwide. Many accommodations lack working CO detectors, and laws vary by country. A portable carbon monoxide alarm is an inexpensive, potentially life-saving device that should be in every traveler’s suitcase. We recommend the First Alert 10-Year Portable CO Alarm.

    Why Carbon Monoxide is a Serious Travel Risk

    Carbon monoxide (CO) is called the silent killer for good reason. It’s invisible, odorless, colorless, and tasteless. You cannot detect it with your senses.

    What Makes Carbon Monoxide So Dangerous?

    Carbon monoxide is produced from any fuel-burning source, including:

    • Furnaces and boilers
    • Gas stoves and ovens
    • Water heaters
    • Fireplaces and chimneys
    • Dryer vents
    • Heating and air conditioning systems
    • Generators (common in areas with power issues)
    • Cars and boats

    According to the Journal of Travel Medicine, CO has 200 to 250 times greater attraction to the hemoglobin in your blood than oxygen. When carbon monoxide leaks into a room, it aggressively displaces oxygen in your bloodstream, essentially suffocating you from the inside out.

    The Centers for Disease Control and Prevention (CDC) reports that approximately 400 people in the United States die from unintentional carbon monoxide poisoning every year, with thousands more requiring emergency treatment.

    ⚠️ Critical Fact: You can be poisoned and die in your sleep without ever waking up. Early symptoms mimic common travel ailments like jet lag or food poisoning, making CO especially dangerous for travelers.

    Why Hotels and Rentals Are High-Risk

    The problem isn’t just that CO exists. It’s that when we travel, we enter unfamiliar spaces where:

    • Systems may be improperly installed
    • Equipment is poorly maintained
    • Ventilation is inadequate
    • CO detectors are missing, broken, or have dead batteries
    • Laws requiring CO detectors vary by country and region

    This can happen anywhere. Luxury five-star hotels. Budget motels. Vacation rentals. Historic inns (which we love staying in, but their old heating systems can be risky). Brand-new condos. Airbnbs. No accommodation type is immune.

    And here’s the kicker: you can’t count on the property having a working carbon monoxide detector. Standards vary wildly around the world, and even in countries with strict laws, enforcement is inconsistent.

    Symptoms of Carbon Monoxide Poisoning

    Early detection is absolutely critical because symptoms progress quickly:

    Early symptoms (often mistaken for other illnesses):

    • Dizziness and confusion
    • Headache
    • Nausea
    • Fatigue and weakness
    • Shortness of breath

    Advanced symptoms:

    • Difficulty walking
    • Increased heart rate
    • Chest pain
    • Vision problems
    • Loss of consciousness

    Severe exposure leads to:

    • Brain damage
    • Organ failure
    • Death
    💡 Important: If you suspect carbon monoxide poisoning, get to fresh air immediately, call emergency services, and seek medical attention. The American Red Cross recommends that even if symptoms improve, CO exposure can cause delayed neurological effects.

    Real Stories: When CO Poisoning Happens to Travelers

    I’m not being paranoid or overly cautious. These are real stories of travelers who encountered carbon monoxide poisoning. Some survived. Some didn’t.

    The Iowa Family in Tulum, Mexico

    A family of four from Iowa died in their sleep when carbon monoxide mysteriously leaked into their vacation condo in Tulum, Mexico.

    They went to bed one night during what should have been a dream vacation. None of them woke up.

    The source of the CO was never definitively identified, but investigators suspected a faulty water heater or gas system. The rental had no carbon monoxide detector.

    The Ireland Vacation That Nearly Ended in Tragedy

    One traveler lived to tell his story but suffered severe consequences after CO poisoning during a trip to Ireland.

    He woke up in the middle of the night to use the bathroom and passed out. He came to, tried again, and passed out a second time, this time suffering a seizure. When his wife awoke to the sound of him hitting the floor, she also passed out.

    Suspecting carbon monoxide, he managed to tell his daughter to open the window and stay by it. They survived, but he reported suffering carbon monoxide symptoms even months after the incident, including persistent headaches and cognitive issues.

    The apartment they rented had no CO detector.

    These aren’t isolated incidents. Stories like these happen every year, all over the world. Most don’t make international news.

    The Common Thread

    In nearly every case of traveler CO poisoning, the accommodation either had no carbon monoxide detector or had one that wasn’t working. You cannot rely on properties to protect you. You have to protect yourself.

    Why We’re Extra Cautious in Historic Hotels and Old Inns

    We absolutely love staying in historic hotels and charming old inns. There’s something magical about sleeping in a building with centuries of stories. These properties are beautiful, well-maintained, and offer incredible hospitality. But here’s the reality: historic buildings often have older infrastructure that can pose higher carbon monoxide risks.

    What makes historic properties higher-risk for CO:

    • Aging heating systems – Older boilers and furnaces may have cracks or inefficient combustion
    • Original fireplaces – Charming but potentially problematic chimneys and flues
    • Period-appropriate ventilation – Built before modern ventilation standards
    • Vintage water heaters – May not have the same safety features as newer models
    • Retrofitted gas systems – Modern gas lines installed in old buildings
    • Complex layouts – Additions and renovations over decades can create ventilation issues

    ⚠️ Important Note: This doesn’t mean historic hotels are unsafe. Most are meticulously maintained and inspected. But the combination of older systems and beautiful period features means we’re always extra vigilant with our portable CO detector. It’s a small precaution that gives us complete peace of mind.

    That’s exactly why our First Alert CO detector comes with us to every single historic property we visit. It takes 10 seconds to set up on the nightstand, and we sleep soundly knowing we’re protected.

    First Alert portable carbon monoxide detector for travel safety

    Best Portable Carbon Monoxide Detector for Travel: First Alert Review

    After researching options and using it for years while traveling to historic hotels, old inns, and vacation rentals, my top recommendation is the First Alert 10-Year Sealed Battery Carbon Monoxide Alarm.

    Why This Is the Best Travel CO Detector

    Feature Details Why It Matters for Travel
    10-Year Battery Sealed lithium battery lasts entire life of alarm No battery changes needed while traveling; always ready to use
    Compact Size 4.8 x 4.8 x 1.8 inches Fits easily in suitcase; doesn’t take up valuable packing space
    Loud Alarm 85 decibel alert Wakes even deep sleepers; audible throughout hotel room
    LED Display Shows temperature with blue backlight Easy to read at night; dual purpose as room thermometer
    No Installation Just set it on nightstand or dresser Ready to use in seconds; no tools or wall mounting required
    TSA Compliant Allowed in carry-on and checked bags Can pack without airport hassles
    Price Around $50 One-time investment for 10 years of protection

    First Alert carbon monoxide alarm with LED displayFirst Alert carbon monoxide alarm with LED display

    How It Works

    The First Alert CO alarm uses an electrochemical sensor to detect carbon monoxide in the air. When dangerous levels are detected, it sends out a sharp, loud 85-decibel beep that will wake you up immediately.

    This model meets UL and NFPA safety standards for carbon monoxide detection, ensuring reliable performance when you need it most.

    The LED display shows the current room temperature (a nice bonus feature), and the blue backlight makes it easy to read in the middle of the night without being too bright or disruptive.

    Real-World Travel Testing

    We’ve taken this detector to historic hotels with old heating systems, charming country inns with fireplaces, mountain cabins, beach rentals with questionable ventilation, and countless Airbnbs. It’s incredibly easy to pack, set up takes literally 10 seconds, and it gives us peace of mind every single night.

    The temperature display is actually useful too. We’ve discovered some hotels keep rooms way too warm or cold, and we can adjust accordingly.

    Pros and Cons

    ✅ Pros:

    • No battery maintenance for 10 years
    • Compact and travel-friendly size
    • No installation or tools required
    • Loud enough to wake heavy sleepers
    • LED temperature display is useful bonus
    • TSA-approved for air travel
    • Reliable electrochemical sensor technology
    • Wall mount option available (though not needed for travel)

    ❌ Cons:

    • Higher upfront cost than battery-replaceable models (but worth it for travel convenience)
    • Must be replaced after 10 years (alarm will notify you)
    • Slightly bulkier than some ultra-compact models

    Where to Buy

    You can purchase the First Alert 10-Year Sealed Battery Carbon Monoxide Alarm on Amazon for around $50.

    It’s a one-time investment that provides protection for a decade of travel. When you consider what you spend on travel insurance, nice luggage, or even a good packing organizer, $50 for something that could literally save your life is beyond reasonable.

    Portable carbon monoxide detector on hotel nightstandPortable carbon monoxide detector on hotel nightstand

    How to Use Your Portable CO Detector While Traveling

    Step-by-Step Travel Setup

    1. Pack it in an accessible place
    Keep your CO detector in your carry-on or near the top of your suitcase. You want to be able to set it up as soon as you arrive at your accommodation.

    2. Place it strategically in your room
    Set the detector on your nightstand, dresser, or bedside table. It should be:

    • Near where you sleep (within earshot)
    • Away from windows and doors (drafts can affect readings)
    • Not blocked by luggage or other items
    • On a flat, stable surface

    3. Check that it’s working
    The First Alert model has a test button. Press it to verify the alarm is functioning. You should hear the loud beep and see the LED display light up.

    4. Leave it on for your entire stay
    The detector should remain active 24/7 while you’re in the room. The 10-year battery means you never have to worry about it dying.

    5. What to do if the alarm goes off

    See also

    Three panel collage showing fall activities in Milford Pennsylvania including woman on firepit balcony at Hotel Fauchere, colorful autumn downtown street with historic buildings, and Raymondskill Falls waterfall cascades in Pocono Mountains"Three panel collage showing fall activities in Milford Pennsylvania including woman on firepit balcony at Hotel Fauchere, colorful autumn downtown street with historic buildings, and Raymondskill Falls waterfall cascades in Pocono Mountains"
    • Immediately evacuate the room and get to fresh air
    • Alert hotel staff or property management
    • Call emergency services (911 in US, 112 in Europe, or local emergency number)
    • Do NOT re-enter the room until it’s been inspected and declared safe
    • Seek medical attention even if you feel fine (CO effects can be delayed)

    ⚠️ Never Ignore the Alarm: Even if you feel fine, if the CO detector goes off, take it seriously. Carbon monoxide poisoning can make you feel confused or drowsy, which might cause you to dismiss the alarm. Always evacuate first, ask questions later.

    Packing Tips for Air Travel

    The First Alert CO detector is TSA-compliant and can be packed in either carry-on or checked luggage. Here are some tips:

    • Carry-on is preferable (you’ll have it immediately upon arrival)
    • Wrap it in soft clothing to prevent damage
    • Keep the instruction manual (it explains it’s a CO detector if TSA asks)
    • No special declarations needed at security

    We’ve traveled with ours through dozens of airports in multiple countries and have never had any issues. Check out our full guide on packing tips for more travel essentials.

    Additional Hotel and Rental Safety Tips

    While a portable CO detector is your best protection, here are other ways to reduce your carbon monoxide risk while traveling:

    Before You Book

    • Ask if the property has carbon monoxide detectors installed
    • Read recent reviews for any mentions of safety concerns
    • Choose accommodations with good ventilation when possible
    • Be extra cautious with older buildings or properties in regions with lax safety standards

    When You Arrive

    • Check if there’s a CO detector in the room (many won’t have one)
    • If there is one, test it if possible
    • Look for fuel-burning appliances (gas stoves, fireplaces, water heaters)
    • Note the location of windows and how to open them quickly
    • Request a room away from furnace rooms, parking garages, or loading docks

    During Your Stay

    • Open windows periodically for fresh air circulation
    • Never use generators, grills, or camping stoves indoors (the U.S. Consumer Product Safety Commission reports that portable generators produce more CO than modern cars and can be deadly in enclosed spaces)
    • Don’t run your car in an attached garage (even with the door open)
    • Report any strange smells or sounds from heating systems immediately
    • Trust your instincts – if something feels off, request a room change

    Additional Travel Safety Resources

    Carbon monoxide safety is just one aspect of travel security. Make sure you’re prepared with:

    Travel essentials including First Alert carbon monoxide detectorTravel essentials including First Alert carbon monoxide detector

    Common Questions About Travel CO Detectors

    Do hotels have carbon monoxide detectors?

    It varies widely. In the United States, many states require CO detectors in hotels, but enforcement is inconsistent. Internationally, requirements vary significantly by country. Many hotels, motels, and vacation rentals have no CO detectors at all, or have detectors with dead batteries. You cannot rely on the property to protect you.

    Can I bring a carbon monoxide detector on a plane?

    Yes. Portable carbon monoxide detectors like the First Alert model are TSA-compliant and allowed in both carry-on and checked baggage. You don’t need to declare it or remove it during security screening. We’ve flown with ours dozens of times without any issues.

    How often do I need to replace a travel CO detector?

    The First Alert 10-Year model has a sealed battery that lasts for the entire life of the unit. After 10 years, the alarm will notify you that it needs to be replaced, and you’ll purchase a new unit. This is much more convenient for travel than models requiring regular battery changes.

    Is a portable CO detector as effective as a permanent one?

    Yes. Portable CO detectors use the same electrochemical sensor technology as permanently installed units. The First Alert model meets UL safety standards and provides the same level of protection. The main difference is portability and power source (sealed battery vs. hardwired).

    What if my CO detector goes off but I feel fine?

    Evacuate immediately anyway. Carbon monoxide poisoning can cause confusion and drowsiness, which might make you unable to recognize the danger. Additionally, CO effects can be delayed, and you may feel fine initially but develop serious symptoms later. Always get to fresh air, alert property management, call emergency services, and seek medical evaluation.

    Do I need a CO detector for every type of accommodation?

    Yes. Carbon monoxide can leak in any building with fuel-burning appliances or systems. This includes luxury hotels, budget motels, vacation homes, Airbnbs, cabins, RVs, and boats. The type or cost of accommodation doesn’t determine CO risk. Old buildings and properties in areas with lax safety regulations pose higher risks, but CO incidents can happen anywhere.

    Can I use my home CO detector for travel?

    If it’s portable and battery-powered, yes. However, most home CO detectors are either hardwired or require regular battery changes, making them less convenient for travel. The First Alert 10-Year model is specifically ideal for travel because of its sealed battery and compact size.

    Will a CO detector detect natural gas leaks?

    No. Carbon monoxide detectors only detect CO, not natural gas (methane) or propane. Natural gas has an added odor (smells like rotten eggs) to help detect leaks. If you smell gas, evacuate immediately and call emergency services.

    How much does a good travel CO detector cost?

    The First Alert 10-Year model costs around $50. While there are cheaper options available, the sealed 10-year battery and reliability make this model worth the investment. It works out to about $5 per year of protection.

    The Bottom Line on Travel Carbon Monoxide Safety

    Carbon monoxide poisoning is a real, preventable risk that kills travelers every year. You can’t see it, smell it, or taste it. You can’t count on hotels or vacation rentals to have working detectors. And by the time you experience symptoms, it may be too late.

    A portable carbon monoxide detector is one of the most important safety items you can pack. It’s more critical than travel insurance, more valuable than an expensive suitcase, and more life-saving than any other travel gadget.

    The First Alert 10-Year Sealed Battery Carbon Monoxide Alarm is compact, reliable, maintenance-free, and gives you peace of mind everywhere you travel.

    Whether you’re traveling solo, with friends, family, or pets to luxury hotels or historic inns, budget motels or vacation rentals, this small device could save your life.

    More Travel Safety & Planning Resources

    This travel safety guide was last updated on February 13, 2026. We regularly review new carbon monoxide detector models and update our recommendations based on real-world travel testing.

     

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • 5 Most Romantic Hotels in Maryland & the Eastern Shore | Better Living

    Most couples searching for romantic Maryland getaways miss the best properties entirely. While chain hotels dominate search results, the Eastern Shore hides intimate inns with private cottages, waterfront boutique hotels with impeccable service, and modern retreats where every detail anticipates what couples need. After staying at dozens of Maryland properties, these five stand out for creating genuine romantic experiences.

    Why the Eastern Shore Dominates Maryland’s Romantic Hotel Scene

    The Chesapeake Bay region delivers what couples actually want: seclusion without isolation, exceptional dining within walking distance, and settings that encourage you to slow down and reconnect.

    Four of these five hotels sit on or near the water. That’s not coincidence. Waterfront locations – even in the winter,  provide sunset views, peaceful morning walks, and that sense of escape that makes romantic getaways work. The fifth – Brampton 1860 – trades water views for 35 acres of private estate grounds where you won’t see another soul if you don’t want to. But even here, the waterfront is just a 2 minute drive into quaint Chestertown.

    From historic cottages with soaking tubs to modern suites with floor-to-ceiling bay views, each property earned its ranking through exceptional attention to couples, distinctive romantic amenities, and those intangible qualities that make you extend your checkout time.

    Quick Comparison: Maryland’s Most Romantic Hotels

    Hotel Location Price Range Best For
    Brampton 1860 Chestertown $$-$$$ Ultimate privacy & seclusion
    The Wildset Hotel St. Michaels $$-$$$ Boutique charm & walkable town
    The Oaks Waterfront Easton $$$ Intimate luxury & pampering
    Hyatt Place Kent Narrows Kent Narrows $$ Waterfront views & dining scene
    Merriweather Lakehouse Columbia $$-$$$ Modern lakefront & rooftop pool

    1. Brampton 1860 – Chestertown: The Ultimate Romantic Escape

    Interior of Marley's Cottage at Brampton 1860 showing king bed, cozy furnishings, red accent wall, fireplace, and French doors opening to private patio for romantic getaways Inside Marley’s Cottage at Brampton 1860 | Photo: Better Living

    At a Glance

    • Location: 25227 Chestertown Road, Chestertown, MD
    • Price Range: $$-$$$ ($229-$450)
    • Romantic Highlights: Private cottages, Japanese soaking tubs, wood-burning fireplaces, 35-acre estate
    • Best For: Couples seeking total seclusion and historic charm
    • Book: BramptonInn.com

    What Makes Brampton 1860 Maryland’s Most Romantic Hotel

    Brampton 1860 takes the top spot because it delivers something increasingly rare: genuine seclusion combined with thoughtful luxury.

    The private cottages scattered across 35 acres create your own world. Marley’s Cottage, hidden behind an old barn’s red door, offers 1,000 square feet of complete privacy. The elevated bedroom overlooks a wood-burning fireplace. The screened porch features a deep Japanese soaking tub facing meadows where deer wander at dusk.

    This isn’t a hotel where you’re steps from other guests. You’re tucked away in your own retreat, yet just a two-minute walk to the Manor House for farm-to-table breakfasts featuring eggs from Brampton’s chickens.

    Sage green cottage with white trim and covered porch at Brampton 1860, surrounded by lush gardens and lawns, offering private romantic accommodations
    Sage green cottage with white trim and covered porch at Brampton 1860, surrounded by lush gardens and lawns, offering private romantic accommodations Marley’s Cottage: 1,000 square feet of private paradise | Photo: Better Living

    Romantic Experiences at Brampton 1860

    The magic happens in the details. Daily afternoon tea at 4:00 PM brings couples together in the Manor House over wine, fresh-baked pastries, and conversation with other guests and the passionate innkeepers, Dave and Hilari Rinehart.

    The Signature Steampot dinner delivered to your cottage creates an unforgettable evening. Local crabs, shrimp, clams, sweet corn, and kielbasa arrive ready to enjoy on your private porch as the sun sets over the meadow.

    Evenings by the fire pit under the stars. Morning walks through gardens at peak bloom. Fruit picking from the property’s trees. Every moment feels deliberately crafted for connection.

    Brampton 1860's Manor House illuminated at twilight with warm golden lighting highlighting the brick facade and wraparound porch, framed by mature trees under a starlit sky
    Brampton 1860's Manor House illuminated at twilight with warm golden lighting highlighting the brick facade and wraparound porch, framed by mature trees under a starlit sky Summer evening magic at Brampton’s historic Manor House | Photo: Better Living

    Why Couples Love Brampton 1860

    The hands-on hosts make the difference. Dave and Hilari don’t just run Brampton – they care for it and share that passion with guests. Their enthusiasm for the property’s history, the Certified Wildlife Habitat designation, and creating memorable stays shows in every interaction.

    Squeaky, the 14-year-old black cat who truly runs the place, adds unexpected charm. He’ll join you for dinner, follow you to breakfast, and make himself comfortable at the evening fire pit like the seasoned host he is.

    ❤️ Perfect for: Anniversary celebrations, proposals, couples who value privacy over proximity to nightlife, history lovers, nature enthusiasts, and anyone seeking a true escape.

    Read Our Complete Brampton 1860 Review

    2. The Wildset Hotel – St. Michaels: Boutique Romance in America’s Most Beautiful Town

    King bed with open patio door at The Wildset Hotel revealing morning light and outdoor seating area, creating romantic coastal retreat atmosphere
    King bed with open patio door at The Wildset Hotel revealing morning light and outdoor seating area, creating romantic coastal retreat atmosphere A beautiful morning at The Wildset Hotel | Photo: Better Living

    At a Glance

    • Location: 209 N Talbot St, St. Michaels, MD
    • Price Range: $$-$$$
    • Romantic Highlights: Fireplaces, balconies, soaking tubs, nightly s’mores, onsite fine dining
    • Best For: Couples who want boutique luxury in a walkable historic town
    • Book: TheWildset.com

    What Makes The Wildset Hotel Irresistibly Romantic

    The Wildset captures that sweet spot between intimate boutique hotel and prime location. Set in three renovated 19th-century buildings in the heart of St. Michaels – Conde Nast’s “Most Beautiful Town in Maryland” – you’re steps from waterfront dining, antique shops, and picturesque streets.

    Each of the 34 suites brings its own character. Modern farmhouse decor meets Scandinavian simplicity. Parachute bedding ensures restful sleep. Grown Alchemist bath products add spa-quality touches. Premium suites feature fireplaces, private balconies, and deep soaking tubs perfect for unwinding together.

    Bright, elegantly furnished room at The Wildset Hotel featuring cream sofa, large windows with views, warm wood floors, and coastal artwork creating romantic atmosphere
    Bright, elegantly furnished room at The Wildset Hotel featuring cream sofa, large windows with views, warm wood floors, and coastal artwork creating romantic atmosphere Room 102 at The Wildset Hotel | Photo: Better Living

    The magic extends beyond your room. Complimentary cruiser bikes invite exploration of the 1.3-mile St. Michaels Nature Trail. Evening s’mores kits and a crackling fire pit create opportunities to connect under the stars.

    Romantic Dining at Ruse

    The onsite restaurant Ruse deserves special mention. Named in honor of St. Michaels being “The Town that Fooled the British,” this modern American seafood restaurant serves some of the best food we’ve experienced at any hotel.

    The roasted local oysters with garlic breadcrumbs and urfa biber are buttery perfection. Seared scallops with local pea puree showcase the season’s best. The intimate patio under twinkling lights at sunset creates exactly the atmosphere you want for a romantic dinner.

    Hand holding s'mores in front of firepit at The Wildset Hotel creating cozy romantic evening atmosphere
    Hand holding s'mores in front of firepit at The Wildset Hotel creating cozy romantic evening atmosphere The Wildset offers free s’mores kits and a nightly firepit | Photo: Better Living

    Why Couples Choose The Wildset

    Location matters. You can walk to exceptional restaurants like Bistro St. Michaels and Carpenter Street Saloon, browse antique shops, and enjoy sunset views at the marina. Yet you return to a peaceful, beautifully designed retreat.

    The nightly fire pit gatherings strike a perfect balance. You can mingle with other couples or claim a quiet corner for yourselves. Either way, you’re surrounded by flickering flames and the peaceful Eastern Shore evening.

    ❤️ Perfect for: Couples who want boutique luxury without isolation, foodies seeking exceptional dining, active couples who enjoy biking and walking, anyone charmed by historic small-town atmosphere.

    Explore St. Michaels: Your Complete Travel Guide

    3. The Oaks Waterfront Hotel – Easton: Intimate Luxury with Impeccable Service

    Serene master bedroom at The Oaks featuring platform bed with white linens, large windows overlooking grounds, and coastal artwork creating peaceful romantic retreat
    Serene master bedroom at The Oaks featuring platform bed with white linens, large windows overlooking grounds, and coastal artwork creating peaceful romantic retreat Cottage 3 bedroom with woodland views and luxury amenities | Photo: Better Living

    At a Glance

    • Location: Easton, MD (on Oak Creek off the Chesapeake Bay)
    • Price Range: $$$
    • Romantic Highlights: Only 15 total accommodations, heated bathroom floors, private waterfront cottages, 40-foot yacht
    • Best For: Couples wanting to be pampered without pretension
    • Book: The-Oaks.com

    What Makes The Oaks Waterfront Hotel Special

    With only 11 rooms in the main building and 4 waterfront cottages, The Oaks delivers something increasingly rare: the attentiveness of a luxury property combined with genuine warmth.

    The level of service rivals The Four Seasons or Ritz-Carlton. Fresh flowers appear daily throughout the property. The restaurant looks picture-perfect at every meal. Premium amenities fill the rooms – quality furnishings, exceptional linens, plush robes. Yet the staff greets you by name and makes you feel like welcomed friends rather than hotel guests.

    Bright cottage living room at The Oaks featuring cream sofa, plaid armchairs, round glass coffee table, and large windows with water views creating romantic waterfront atmosphere
    Bright cottage living room at The Oaks featuring cream sofa, plaid armchairs, round glass coffee table, and large windows with water views creating romantic waterfront atmosphere Cottage 3 living room with water views at The Oaks | Photo: Better Living

    Cottage 3, where we stayed, showcases this perfectly. The spacious layout includes a king bed with luxury linens, heated bathroom floors, a deep soaking tub, and a covered porch overlooking Oak Creek. The complimentary chocolate chip cookies baked onsite became a daily highlight.

    Romantic Dining at The Oak Room

    Chef Dave’s cuisine at The Oak Room rivals much larger hotels. The Corn and White Truffle Agnolotti with butter-poached lobster and crisp prosciutto is pure indulgence. Maryland Crab Cakes over forest mushroom risotto highlight the region’s best ingredients.

    Sujoy’s cocktail artistry at the bar transforms drinks into theater. Each cocktail is crafted right in front of you – from the Chocolate Espresso Martini with freshly grated chocolate to the perfectly balanced Spicy Margarita.

    The intimate dining room with water views seats just enough couples to feel special without feeling crowded. Tuesday through Thursday dinner service creates a more exclusive atmosphere.

    Intimate two-person dining table at The Oak Room with white linens, wine glasses, and formal place settings beside large windows overlooking Oak Creek with yacht visible at dock
    Intimate two-person dining table at The Oak Room with white linens, wine glasses, and formal place settings beside large windows overlooking Oak Creek with yacht visible at dock Waterfront dining room table at The Oak Room with sunset yacht views | Photo: Better Living

    Why The Oaks Stands Out for Romance

    The 10-acre waterfront property provides space to breathe. Adirondack chairs dot the lawn facing the water. The evening fire pit brings couples together under the stars. The 40-foot Hinckley yacht “Overcomer” waits at the private pier for sunset cruises (weather permitting).

    The intimate size means you’ll likely meet other guests naturally – at the fire pit, during breakfast, or over cocktails. We had wonderful conversations with both fellow travelers and staff throughout our stay. Yet you never feel crowded.

    Golf cart rides across the grounds and a luxury SUV for shopping and dining trips in nearby Easton and St. Michaels add convenience without fuss.

    ❤️ Perfect for: Couples seeking luxury without stuffiness, foodies who appreciate exceptional cuisine and craft cocktails, travelers who value attentive service, anyone wanting to be thoroughly pampered.

    Read Our Complete Oaks Waterfront Hotel Review

    4. Hyatt Place Kent Narrows & Marina – Kent Narrows: Modern Waterfront Romance

    Brilliant pastel sunset over Chesapeake Bay at Kent Narrows with dramatic sky reflecting on calm water and silhouetted boats creating romantic waterfront scene
    Brilliant pastel sunset over Chesapeake Bay at Kent Narrows with dramatic sky reflecting on calm water and silhouetted boats creating romantic waterfront scene Stunning sunset views from Hyatt Place Kent Narrows | Photo: Better Living

    At a Glance

    • Location: 3028 Kent Narrow Way S, Grasonville, MD (Fisherman’s Village)
    • Price Range: $$
    • Romantic Highlights: Waterfront suites with balconies, 2000 sq ft of deck space, adult-focused atmosphere, sunset views
    • Best For: Couples who love waterfront dining and spectacular bay views
    • Book: Hyatt.com

    What Makes Hyatt Place Kent Narrows Romantically Appealing

    Kent Narrows remains one of Maryland’s best-kept secrets – a laid-back waterfront destination surrounded by stunning Chesapeake Bay views in almost every direction. The Hyatt Place sits at the heart of Fisherman’s Village, where you can walk to exceptional seafood restaurants and dockside bars.

    The 120 modern rooms bring coastal-inspired serenity with natural woods and calming blues and grays. Book a waterfront suite with a private balcony to watch boats cruise by on Prospect Bay. The spacious suites include kitchenettes, 55-inch flat screens, and plush bedding.

    Expansive bay view from Hyatt Place Kent Narrows balcony showing docks, piers, and boats cruising by on calm water creating serene romantic atmosphere
    Expansive bay view from Hyatt Place Kent Narrows balcony showing docks, piers, and boats cruising by on calm water creating serene romantic atmosphere The view from the balcony suites at Hyatt Place Kent Narrows | Photo: Better Living

    What sets this property apart is the atmosphere. While families visit, the vibe skews adult. The expansive waterfront deck, fire pit at sunset, and proximity to lively but not rowdy dockside dining creates the perfect balance for couples.

    Romantic Waterfront Dining Within Walking Distance

    Location makes or breaks a romantic getaway, and Hyatt Place Kent Narrows nails it. You’re steps from Fisherman’s Inn with its award-winning Coconut Cream Pie and collection of 300+ antique oyster plates. The iconic Fisherman’s Crab Deck delivers the authentic Maryland experience – fresh steamed crabs, orange crushes, and sunset views.

    Big Owl Tiki Bar next door brings Key West vibes to the Chesapeake. Soft shell crab tacos, tropical cocktails, and live music create the perfect casual evening. The famous Kent Narrows Nutty Buddy ice cream cone is mandatory.

    Walk back to your waterfront suite after dinner and enjoy the bay views from your private balcony. Or grab drinks from The Placery lobby bar and relax by the fire pit as the sun sets.

    Modern living and dining area in waterfront suite at Hyatt Place Kent Narrows with kitchenette, comfortable seating, and coastal decor perfect for romantic stays
    Modern living and dining area in waterfront suite at Hyatt Place Kent Narrows with kitchenette, comfortable seating, and coastal decor perfect for romantic stays The living and dining area in a waterfront suite at Hyatt Place Kent Narrows | Photo: Better Living

    Why Couples Choose Hyatt Place Kent Narrows

    The complimentary breakfast served on the dockside terrace starts each day right. Fresh coffee, hot items, and those stunning water views create a peaceful morning routine.

    The 24/7 fitness center, indoor pool overlooking the marina, and proximity to hiking and biking trails appeal to active couples. Yet the relaxed pace of Kent Narrows makes it equally perfect for doing absolutely nothing but watching boats go by.

    The 40 dock slips behind the property mean boating couples can arrive by water. And the adult-focused atmosphere (without being couples-only) strikes the right balance for a romantic escape.

    ❤️ Perfect for: Couples who love waterfront dining and sunset views, boating enthusiasts, travelers seeking modern comfort with authentic Chesapeake Bay character, anyone who values walkability to restaurants and bars.

    Discover Kent Narrows: Maryland’s Waterfront Hidden Gem

    5. Merriweather Lakehouse Hotel – Columbia: Modern Lakefront Luxury

    Presidential Suite living area at Merriweather Lakehouse Hotel featuring dining table, designer furniture, and panoramic lake views through floor-to-ceiling windows
    Presidential Suite living area at Merriweather Lakehouse Hotel featuring dining table, designer furniture, and panoramic lake views through floor-to-ceiling windows The living area in the Presidential Suite at Merriweather Lakehouse Hotel | Photo: Better Living

    At a Glance

    • Location: 10209 Wincopin Circle, Columbia, MD
    • Price Range: $$-$$$ ($200-400)
    • Romantic Highlights: Floor-to-ceiling lake views, rooftop pool (seasonal), private balconies, pet-friendly
    • Best For: Couples seeking modern luxury near DC/Baltimore, summer pool season visits
    • Book: MerriweatherLakehouse.com

    What Makes Merriweather Lakehouse Hotel Romantic

    This 212-room Marriott Autograph Collection property brings contemporary luxury to Lake Kittamaqundi’s shores. The floor-to-ceiling windows throughout create an ever-present connection to the water – from the lobby to the hallways to your room.

    Lake view rooms with private balconies deliver the full experience. Watching winter birds on the partially frozen lake from your balcony with morning coffee creates surprisingly intimate moments. The separate living areas in suites provide space to truly relax together after exploring Columbia or hiking the 1.4-mile lake trail.

    Luxurious Presidential Suite bedroom at Merriweather Lakehouse featuring elegant canopy bed, premium linens, and floor-to-ceiling windows with panoramic Lake Kittamaqundi views
    Luxurious Presidential Suite bedroom at Merriweather Lakehouse featuring elegant canopy bed, premium linens, and floor-to-ceiling windows with panoramic Lake Kittamaqundi views The bedroom in the Presidential Suite at Merriweather Lakehouse Hotel | Photo: Better Living

    The rooftop pool (open Memorial Day through Labor Day) and Eagle Watch Lounge add resort-style amenities during summer visits. This transforms the property into an ideal warm-weather romantic escape.

    Exceptional Dining at lak Restaurant

    The onsite restaurant lak (pronounced “lake”) serves cuisine that rivals standalone fine dining establishments. The Maryland Crab Cakes over creamy risotto showcase local ingredients beautifully. Corn and White Truffle Agnolotti with a huge piece of lobster claw is pure indulgence.

    The Rookery Bar crafts creative cocktails with quality spirits. Floor-to-ceiling windows ensure you never lose sight of the lake, even while dining.

    The complimentary breakfast from 8:30-9:30 AM features elevated options like Poached Egg with Smoked Salmon over rosti potatoes, Eastern Shore Omelette with jumbo lump crab, and French Toast with Chantilly cream. Starting the day overlooking the water sets the perfect tone.

    Panoramic winter view of Lake Kittamaqundi from Merriweather Lakehouse Hotel showing frozen lake, surrounding trees, and serene natural landscape
    Panoramic winter view of Lake Kittamaqundi from Merriweather Lakehouse Hotel showing frozen lake, surrounding trees, and serene natural landscape A panoramic view from the hotel of Lake Kittamaqundi | Photo: Better Living

    Why Merriweather Lakehouse Appeals to Couples

    The location just 15 minutes from BWI Airport makes spontaneous romantic weekends easy. Columbia’s downtown offers shopping at the Mall of Columbia, dining in the trendy Merriweather District, and concerts at the legendary Merriweather Post Pavilion (15-minute walk).

    Free parking is rare at luxury properties. The pet-friendly policy (no extra fees) means furry companions can join the escape. The 1.4-mile Lake Kittamaqundi trail provides peaceful walks where you’ll spot herons, ospreys, and even bald eagles.

    The modern design and Marriott Bonvoy benefits appeal to couples who appreciate contemporary luxury over historic charm. The 24-hour fitness center with Peloton bikes and quality equipment means no guilt about skipping workouts.

    ❤️ Perfect for: Couples who prefer modern luxury over historic properties, summer visits when the rooftop pool is open, pet owners, nature lovers and birdwatchers, travelers wanting easy access to DC/Baltimore, Marriott Bonvoy members.

    Read Our Complete Merriweather Lakehouse Hotel Review

    Where to Dine: Romantic Restaurants at Each Hotel

    Exceptional dining plays a crucial role in romantic getaways. Here’s where to eat at each property:

    Brampton 1860 Dining Options

    Onsite: Farm-to-table breakfast included with stay, afternoon tea at 4 PM, Signature Steampot dinner delivered to cottage. Seasonal options also availble.

    Nearby in Chestertown: The Kitchen at the Imperial (Chef Steve Quigg’s farm-to-table fine dining), Crow Vineyard (wine tasting and patio dining)

    The Wildset Hotel Dining Options

    Onsite: Ruse Restaurant (modern American seafood, dinner and brunch)

    Nearby in St. Michaels: Bistro St. Michaels (upscale French-Southern fusion), Carpenter Street Saloon (historic tavern), Foxy’s Harbor Grille (waterfront casual)

    The Oaks Waterfront Hotel Dining Options

    Onsite: The Oak Room (fine dining, Tuesday-Thursday evenings), The Rookery Bar & Lounge (craft cocktails), The Osprey Cafe (gourmet coffee and pastries)

    Nearby in Easton/St. Michaels: Bistro St. Michaels, Tiger Lily Easton (creative tacos and fusion)

    Hyatt Place Kent Narrows Dining Options

    Onsite: The Placery (lobby bar with light bites), complimentary breakfast buffet

    Walking Distance in Fisherman’s Village: Fisherman’s Inn (upscale seafood), Fisherman’s Crab Deck (casual waterfront crabs), Big Owl Tiki Bar (tropical drinks and tacos)

    Nearby: Bridges Restaurant (Caribbean-inspired), Dock House (modern coastal), Harris Crab House (traditional Maryland seafood)

    Merriweather Lakehouse Dining Options

    Onsite: lak Restaurant (American fine dining), The Rookery Bar (craft cocktails), The Osprey Cafe (coffee and pastries)

    See also

    Chocolate Popcorn BarkChocolate Popcorn Bark

    Nearby in Columbia: Merriweather District restaurants, Mall of Columbia dining options

    How to Choose the Right Romantic Maryland Hotel

    Choose Brampton 1860 if you want: Complete privacy in a secluded cottage, historic charm, farm-to-table dining, nature immersion, the ultimate romantic escape from reality.

    Choose The Wildset Hotel if you want: Boutique luxury in a walkable historic town, excellent onsite dining at Ruse, easy access to shops and restaurants, modern farmhouse aesthetic, evening s’mores by the fire.

    Choose The Oaks Waterfront Hotel if you want: To be pampered with Four Seasons-level service, intimate property with only 15 accommodations, exceptional cuisine at The Oak Room, waterfront tranquility, adults-only atmosphere.

    Choose Hyatt Place Kent Narrows if you want: Modern waterfront suites with bay views, walkable access to multiple restaurants and bars, adult-focused vibe, spectacular sunsets, best value for waterfront romance.

    Choose Merriweather Lakehouse Hotel if you want: Contemporary lakefront luxury, summer rooftop pool access, proximity to DC/Baltimore, pet-friendly accommodations, hiking and nature right outside your door.

    Best Time to Visit Maryland for Romance

    Spring (April-May): Perfect weather for outdoor activities, fewer crowds than summer, blooming gardens at historic properties like Brampton 1860, comfortable temperatures for exploring towns like St. Michaels.

    Summer (June-August): Peak season for waterfront properties, rooftop pool open at Merriweather Lakehouse, outdoor dining at its finest, sunset cruises and water activities, live music at Kent Narrows restaurants.

    Fall (September-November): Spectacular foliage, harvest season at local vineyards, comfortable hiking weather, cozy fireplaces at The Wildset, fewer crowds after Labor Day.

    Winter (December-February): Lowest rates of the year, cozy romance by the fire, intimate atmosphere, hot chocolate and s’mores, perfect for couples seeking quiet connection.

    Planning Your Romantic Maryland Getaway

    How far in advance to book: For weekend stays at any of these properties, book 4-6 weeks ahead minimum. Special occasions (Valentine’s Day, anniversaries) and peak fall foliage season require 2-3 months advance booking. Cottages at Brampton 1860 and The Oaks book especially quickly.

    Recommended length of stay: Two nights minimum allows you to settle in and truly relax. Three nights lets you explore nearby attractions without rushing. All five properties reward longer stays with their peaceful settings.

    What to pack: Comfortable walking shoes for trails and town exploration, layers for changing weather, binoculars for birdwatching (especially at Brampton 1860 and Merriweather Lakehouse), camera for stunning sunset photos, appetites for incredible dining.

    Getting there: All five properties are within 1-2 hours of Baltimore, Washington DC, and Philadelphia. Brampton 1860 and The Wildset are closest to each other (20 minutes apart) for couples wanting to experience multiple properties. Kent Narrows sits perfectly between the Eastern Shore’s attractions.

    Make Your Maryland Romance Unforgettable

    Maryland’s Eastern Shore and surrounding regions deliver romance in distinctive ways. From Brampton 1860’s secluded cottages to The Oaks’ intimate pampering, from The Wildset’s boutique charm to Hyatt Place Kent Narrows’ waterfront sunsets, each property creates its own romantic magic.

    The best romantic hotel depends on what matters most to you as a couple. Total privacy and nature? Brampton wins. Boutique luxury in a charming town? The Wildset delivers. Being thoroughly pampered? The Oaks excels. Waterfront dining and sunset views? Hyatt Place Kent Narrows nails it. Modern lakefront luxury? Merriweather Lakehouse satisfies.

    What they all share is genuine attention to couples, exceptional dining, beautiful settings, and that indefinable quality that makes you want to linger just a bit longer before checking out.

    Your perfect Maryland romantic escape is waiting. The only question is which one to book first.

    Frequently Asked Questions About Romantic Hotels in Maryland

    What is the most romantic hotel in Maryland?

    Brampton 1860 in Chestertown takes the top spot for most romantic hotel in Maryland. The private cottages offer complete seclusion on a 35-acre estate, with features like Japanese soaking tubs, wood-burning fireplaces, and private porches overlooking meadows. The combination of privacy, historic charm, farm-to-table dining, and attentive hosts creates an unmatched romantic atmosphere.

    Which Maryland hotel is best for anniversaries?

    The Oaks Waterfront Hotel in Easton is ideal for anniversaries. With only 15 total accommodations, the intimate property provides Four Seasons-level service and pampering. Private waterfront cottages, exceptional dining at The Oak Room, heated bathroom floors, and thoughtful touches like fresh daily flowers create a celebration-worthy experience. The staff’s genuine warmth makes special occasions feel truly special.

    Where should couples stay in St. Michaels, Maryland?

    The Wildset Hotel is the best choice for couples in St. Michaels. The boutique property offers 34 unique suites in renovated 19th-century buildings right in the heart of town. You’re steps from waterfront dining, antique shops, and the harbor, yet return to modern farmhouse luxury with fireplaces, soaking tubs, and complimentary bikes. The onsite restaurant Ruse serves exceptional cuisine, and evening s’mores by the fire pit add romantic touches.

    What is the best waterfront romantic hotel on the Chesapeake Bay?

    Hyatt Place Kent Narrows offers the best combination of waterfront location, value, and romantic atmosphere on the Chesapeake Bay. The modern waterfront suites with private balconies provide stunning bay views and sunsets. You can walk to multiple excellent restaurants and bars in Fisherman’s Village, creating easy romantic evenings. The adult-focused atmosphere, expansive deck space, and fire pit overlooking the water enhance the romantic setting.

    Do any romantic Maryland hotels allow pets?

    Yes, both Merriweather Lakehouse Hotel and Hyatt Place Kent Narrows are pet-friendly with no additional pet fees. The Oaks Waterfront Hotel also welcomes well-behaved dogs. Some cottages at Brampton 1860 (Russell’s Cottage and Robin’s Nest) accept pets, though these book quickly. Always inform the property when booking that you’re traveling with a pet.

    Which Maryland hotel has the best romantic dining?

    This depends on your preference. Ruse at The Wildset Hotel serves creative modern American seafood in an intimate setting. The Oak Room at The Oaks Waterfront Hotel offers elevated cuisine with Chef Dave’s artistry and Sujoy’s craft cocktails. Brampton 1860’s Signature Steampot delivered to your private cottage creates a uniquely romantic dining experience. All three provide exceptional food in romantic atmospheres.

    What is the most secluded romantic hotel in Maryland?

    Brampton 1860 offers the most seclusion. Private cottages scattered across 35 acres provide complete privacy, yet you’re just a short walk to the Manor House for meals and amenities. Marley’s Cottage, hidden behind a barn’s red door, exemplifies this seclusion – you feel like you’ve discovered a secret world. The natural surroundings, Certified Wildlife Habitat designation, and lack of nearby development enhance the secluded atmosphere.

    Are these Maryland romantic hotels good for proposals?

    Absolutely. Brampton 1860’s private cottages and grounds offer intimate settings for proposals. The Oaks Waterfront Hotel’s yacht sunset cruises (weather permitting) create memorable proposal moments. The Wildset Hotel’s fire pit area under the stars or The Rookery Bar’s sunset views at Merriweather Lakehouse both work beautifully. Contact properties in advance – they’re experienced with proposals and can help coordinate special touches.

    Which Maryland hotel is best for a romantic weekend from DC or Baltimore?

    Merriweather Lakehouse Hotel in Columbia is most convenient, just 15 minutes from BWI Airport and under an hour from both DC and Baltimore. This makes spontaneous romantic weekends easy. The modern luxury, floor-to-ceiling lake views, and rooftop pool (summer only) provide a complete escape despite the proximity to cities. Free parking is an added bonus.

    Do these romantic hotels have minimum stay requirements?

    Weekend minimum stays vary by property and season. Brampton 1860 and The Oaks often require two-night minimums on weekends during peak season. The Wildset Hotel, Hyatt Place Kent Narrows, and Merriweather Lakehouse typically don’t have minimums, though this can change during holidays or special events. Always check directly with properties when booking, especially for holiday weekends.

    What makes the Eastern Shore good for romantic getaways?

    The Eastern Shore combines proximity to major cities with a slower pace of life. Historic towns like St. Michaels and Chestertown offer walkable charm without crowds. Waterfront locations provide stunning sunset views. Farm-to-table dining showcases the region’s bounty. The Chesapeake Bay creates a scenic backdrop for every moment. Close enough for weekend trips, yet far enough to feel like a true escape.

    Can you visit multiple romantic Maryland hotels in one trip?

    Absolutely. Brampton 1860 in Chestertown and The Wildset Hotel in St. Michaels are only 20 minutes apart, making them perfect for a split-stay romantic tour. The Oaks in Easton is 15 minutes from St. Michaels. Hyatt Place Kent Narrows sits between these properties. A 4-5 day trip could include stays at 2-3 properties, experiencing different romantic styles while exploring the Eastern Shore.

    Explore More Maryland & Eastern Shore Destinations:

    Romantic Getaway Destinations:

    More Maryland Hotels & Accommodations:

    Eastern Shore Activities & Dining:

    Seasonal Maryland Experiences:

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • 15 Essential Road Trip Tips and Tricks for 2026

    A road trip is a fun and exciting way to travel and explore new destinations. With so much to see and do, a road trip can be an amazing and unforgettable experience. To make the most of your journey, here are essential road trip tips, tricks, and things you can do before you hit the road to ensure your time traveling is as stress-free and enjoyable as possible.

    1. Have All Your Official Documents Organized

    Sometimes unexpected situations happen on the road. Be sure to organize all your important papers like your car’s registration and insurance card. Keep your license handy in case you get pulled over, and if you’re crossing country borders, make sure your passport isn’t expired. If you have roadside assistance, have that information ready and available. If you don’t, consider joining an automobile club like AAA or contact your insurance company to opt in to their roadside assistance program.

    According to the National Highway Traffic Safety Administration, being prepared with proper documentation can help resolve roadside situations more quickly and safely.

    2. Schedule Your Car for a Maintenance Check

    Besides an awesome itinerary, the most important key to a successful road trip is having your car in working order. Before you take a road trip, give your car basic maintenance. One of the most essential road trip tips is to visit a mechanic before your journey. While you could easily top off fluids like engine coolant on your own, it’s ideal to visit a mechanic so they can get under the hood to ensure your car is in tip-top shape. They can inspect the battery, fuses, hoses, belts, filters, brake system, and tire treads. Don’t forget to fill up that windshield wiper fluid.

    This is also the perfect time to get an oil change. ExxonMobil offers Mobil 1 Annual Protection motor oil which promises a once per year oil change. Mobil 1 Annual Protection provides guaranteed protection for one full year of driving or 20,000 miles per oil change. That means less time waiting around service stations and more money better spent enjoying yourself on the road.

    Regular maintenance can prevent breakdowns and keep you safe on the road.

    3. Bring a Spare Car Key

    I once locked my keys in my car while it was running. Yup. That happened. I guess I got too excited for sushi. Luckily I was in a busy suburban area and my roadside assistance arrived within 20 minutes. But what if I had been somewhere more remote? If I had just had an extra key, all the stress about my car running out of gas while waiting for the tow truck could have been avoided. And my dinner wouldn’t have been ruined. I now always have a spare key with me at all times. Just make sure you carry it on you and don’t leave that one in the car too.

    4. Check Your Cell Phone Coverage Areas

    On a recent road trip, I was upset to find my cell phone coverage wasn’t great in the countryside. This is especially concerning in case you break down somewhere. And losing your GPS signal can be nerve-wracking since you may have no idea where you are. When you plan your journey and have a general idea of where you’ll be driving, check if your cell phone carrier has a strong signal in the area. If not, consider getting a prepaid mobile phone from a different carrier that shows good coverage in spotty areas you’ll be traveling through.

    Not only will you always be able to make phone calls if needed, it’s a good backup in case your phone loses its charge. Also, make sure you have a working cell phone car charger so your phone will never die on the road. The FCC provides helpful information about wireless coverage and emergency services across the country.

    5. Check Your Tires and Tire Pressure

    There’s nothing worse than being stranded on the side of the road. Your tires are what ground your car to the road, so inspecting your tires before a big road trip is vitally important. Make sure the treads are deep enough to ensure adequate traction for quick braking on wet roads or in emergency situations. You may need to replace your tires if the tread is too worn. Tires with good tread will keep you safely grounded on the roads while giving you maximum traction and helping you avoid accidents.

    You’ll also need to check your tire pressure. Be aware the number on the tire’s side is the maximum pressure it can withstand, not the recommended amount. Tires should be slightly less inflated in winter and inflated closer to their maximum recommended pressure in summer. Never over-inflate tires as they could potentially blow out. And always bring a spare tire just in case. To be safe, consult a qualified mechanic if you’re unsure about your tires or want an expert opinion. For more information on choosing quality tires for your road trip, check out our Cooper Tires review.

    6. Plan Your Route with Maps, GPS, and Travel Apps

    Ever hear the expression, “If you don’t plan ahead, you’re planning to fail”? Well, you can’t really fail at a road trip, but you could get lost or miss extraordinary sites and stops. You could take one road when there’s a more scenic route just a couple of minutes down the road. Or you could miss the best-ever apple pie when all you had to do was turn right.

    Having a good idea of where you want to go and what you want to see will make your time much more enjoyable. Check guidebooks, take notes, and do research online. Download a travel app to mark all your preferred points of interest. And do yourself a favor and bring a physical paper map as backup. Technology like cell phone signals and GPS can be lost or break. With a good map, you’ll always be able to find your way.

    Looking for inspiration? Check out these amazing destinations:

    7. Have Cash on Hand and Notify Your Financial Institutions

    Even though most of us use credit and debit cards for everyday purchases, it’s a good idea to have a stash of cash on hand while you’re driving. In fact, it’s a necessity. Not only will you need it for tolls, but if your wallet gets lost or stolen, you’ll at least be prepared. It’s also good to have a spare credit card or two hidden away just in case unexpected expenses arise.

    Be sure to contact your credit card companies and bank to let them know you’ll be traveling. It’s not uncommon to have your credit card account frozen because their computers think your card is being used fraudulently when you’re just on vacation. If you need help managing your travel budget or setting up alerts for your accounts, consider checking with institutions like Needham Bank that offer travel-friendly banking features. Avoid the hassle and drive financially prepared.

    8. Pack an Emergency Kit

    A well-stocked emergency kit can be a lifesaver on a road trip. One of the best road trip tips for safety is to include items like a first-aid kit, flashlight, batteries, jumper cables, basic tools, duct tape, a blanket, bottled water, and non-perishable snacks. According to Ready.gov, you should also include items specific to the season and climate of your destination.

    9. Download Entertainment and Offline Content

    Long stretches of highway can get boring, especially if you’re traveling solo or with kids. Download podcasts, audiobooks, music playlists, and offline maps before you leave. If you’re traveling with children, having tablets loaded with games and movies can make the journey much more pleasant. Don’t forget to pack chargers and car adapters for all your devices.

    10. Plan Your Accommodations in Advance

    While spontaneity can be fun, having at least a rough idea of where you’ll stay each night can reduce stress and ensure you don’t end up scrambling for a room in an unfamiliar area. Consider these great options:

    See also

    Three-panel winter feature showing festive Poinsettia cocktail with cranberries and rosemary garnish surrounded by colorful ornaments, snow-dusted Brampton Manor House exterior with holiday wreaths and lit windows at dusk, Brampton-branded blue ceramic mug filled with hot cocoa topped with marshmallow by fireplace

    11. Stay Healthy on the Road

    Road trips often mean fast food and long periods of sitting, which isn’t great for your health. Pack healthy snacks like nuts, fruit, protein bars, and plenty of water. Take breaks every couple of hours to stretch your legs and get your blood flowing. This will help you stay alert and reduce fatigue.

    The CDC recommends taking regular breaks during long drives to prevent drowsy driving and maintain alertness.

    12. Know Your Route’s Rest Stops and Gas Stations

    Before you leave, map out rest stops, gas stations, and food options along your route. This is especially important if you’re traveling through rural areas where services may be sparse. Apps and websites can help you locate clean rest areas and well-reviewed gas stations along your path.

    13. Prepare for Different Weather Conditions

    Weather can change quickly, especially if you’re traveling across different regions or elevations. Check the forecast for your entire route and pack accordingly. Include rain gear, extra layers, sunscreen, and sunglasses. In winter months, keep an ice scraper, snow brush, and sand or kitty litter for traction in your trunk.

    14. Share Your Itinerary

    Always let someone know your travel plans, including your route, planned stops, and expected arrival times. Check in regularly with family or friends, especially when traveling through remote areas. This simple safety measure can be crucial in case of an emergency.

    15. Enjoy the Journey

    Remember, the journey is just as important as the destination. One of the best road trip tips is to not rush through your trip trying to hit every planned stop. Allow time for spontaneous detours, photo opportunities, and unexpected discoveries. Some of the best road trip memories come from unplanned moments. These road trip tips will help ensure your journey is safe, enjoyable, and unforgettable.

    Looking for more travel inspiration? Explore these destinations:

    Do you have a road trip tip or trick you would like to share? Let us know in the comments how you’ve mastered travel on the road!

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • Forget the Hallmark Movies: This Real-Life Victorian Christmas Festival is Better | Better Living

    I thought I was visiting a standard Victorian street festival. I expected a few costumes, maybe some hot cider, and a quick walk-through.

    Instead, a small Eastern Shore town quietly kicked off my entire holiday season.

    I’d heard about Dickens of a Christmas in Chestertown, Maryland. Held the first weekend of December, it promises a Victorian-themed experience. But what I wasn’t prepared for was how fully the town commits to it, or how quickly a single weekend would shift me into Christmas mode.

    Dickens of a Christmas in Chestertown, MD

    Wide view of Dickens of a Christmas festival on closed High Street showing Victorian-dressed attendees, vendor tents, hay bales, historic clock tower building in background High Street transforms into a Victorian marketplace for the first weekend of December | Photo: Better Living

    Historic Chestertown doesn’t need to pretend. It dates back to 1706 and was founded as a working port on the Chester River, exporting tobacco and grain, and building ships. They even had their own Tea Party in 1774 to protest British taxation.

    That history isn’t just in a museum; it’s visible in the bricks.

    Eighteenth-century buildings line sidewalks that feel largely unchanged. This is exactly why “Dickens” works so well here. When a town already has this much real history, adding period costumes and hay bales doesn’t feel staged.

    It feels like the town is remembering itself.

    I spent both days of the festival staying at Brampton 1860, just four minutes outside of town. While Friday evening set the mood, Saturday was when everything clicked. I spent most of the day wandering High Street, moving slowly, and letting the atmosphere do the work.

    An Era Layered on Top of Another

    Victorian-dressed couple in period costumes sitting on hay bales around small firepit at Dickens of a Christmas festival, woman in red velvet coat with top hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840s London atmosphere
    Victorian-dressed couple in period costumes sitting on hay bales around small firepit at Dickens of a Christmas festival, woman in red velvet coat with top hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840s London atmosphere Victorian London comes to life at Dickens of a Christmas in Chestertown, MD | Photo: Better Living

    What makes Dickens of a Christmas different is that Chestertown doesn’t have to fake the set design.

    The downtown is the real thing. When Victorian costumes, vendor tents, and hay bales appear, it doesn’t feel like a recreation. It feels like one era gently layered on top of another.

    Vendor tents line the closed streets. Hay bales turn into casual seating around firepits. Draft horses pull holiday carriages through the crowds.

    First-person view from inside red holiday carriage showing draft horse pulling through Chestertown residential street with historic homes, passenger wearing Santa hat visible
    First-person view from inside red holiday carriage showing draft horse pulling through Chestertown residential street with historic homes, passenger wearing Santa hat visible The carriage ride offers unique views of Chestertown’s preserved 18th-century architecture | Photo: Better Living

    I took one of the complimentary carriage rides sponsored by Brampton 1860, and it ended up being a highlight. The loop took me through the town’s most charming streets, past historic homes and under bare winter trees.

    From the carriage, the preservation of the town becomes even more apparent. These are not recreations. These are buildings that have stood here for centuries, watching holidays come and go.

    Oyster Stew, Figgy Pudding, and Firepits

    Close-up of oyster stew in white takeout container showing plump oysters in creamy broth with wooden spoon, figgy pudding visible in background
    Close-up of oyster stew in white takeout container showing plump oysters in creamy broth with wooden spoon, figgy pudding visible in background Fresh oyster stew and figgy pudding warm festival-goers on cold December afternoons | Photo: Better Living

    The food was delicious and comforting, which matters when you are outside for hours in December.

    • The Oyster Stew: A generous serving of fresh oysters in a creamy broth. I ate this sitting on a hay bale near a firepit, and it was exactly what the cold afternoon called for.
    • The Figgy Pudding: Beyond the Christmas carol, I had no idea what to expect. It turned out to be a dense, spiced cake that was rich, complex, and unmistakably festive.

    Eating hot stew on a hay bale by the fire, watching people in Victorian costume walk by, has a way of slowing time.

    A Farmers Market That Fits the Scene

    Crowded Chestertown farmers market with vendor tents lining street, shoppers browsing produce and goods on winter day with bare trees overhead
    Crowded Chestertown farmers market with vendor tents lining street, shoppers browsing produce and goods on winter day with bare trees overhead Chestertown’s year-round farmers market folds seamlessly into the Dickens festival weekend

    Chestertown’s Farmers Market runs year-round on Saturdays. During Dickens of a Christmas weekend, the market folds naturally into the festival.

    There was a petting zoo drawing steady crowds, featuring goats, ducks, a mini rooster, and even a Scottish Highland cow with long horns and a shaggy coat. Watching families interact with the animals added a warmth that went beyond the Victorian theme.

    Hands holding colorful miniature rooster with red and black feathers at petting zoo during Dickens festival
    Hands holding colorful miniature rooster with red and black feathers at petting zoo during Dickens festival The farmers market petting zoo features goats, ducks, and even a mini rooster | Photo: Better Living

    This wasn’t just about costumes; it was about the town coming together around something genuinely joyful.

    Quaint Shops in Historic Buildings

    Interior of Twigs and Teacups shop showing holiday merchandise including Christmas mugs, kitchenware, jams, and decorations with shopkeeper in Victorian costume browsing
    Interior of Twigs and Teacups shop showing holiday merchandise including Christmas mugs, kitchenware, jams, and decorations with shopkeeper in Victorian costume browsing Local shops like Twigs and Teacups offer carefully curated gifts and holiday items | Photo: Better Living

    Between festival moments, I stepped inside Chestertown’s shops. These aren’t tourist traps; they are independent and carefully curated.

    See also

    • Walnut and Wool: Decorated with vintage Christmas trees and pressed tin ceilings.
    • Bespoke Chocolates: Handmade truffles displayed beneath a silver tree hung with chocolate ornaments.
    • Book Plate: A reminder of why independent bookstores matter, with floor-to-ceiling shelves and that unmistakable smell of books.
    • Twigs and Teacups: A perfect mix of holiday gifts, kitchenware to toys, and everything in between.
    • Coco’s Pet Center: Specializing in unique, fun, local, handmade products for pets.

    Why Brampton 1860 Was the Perfect Base

    Historic brick Brampton 1860 inn decorated with Christmas lights and wreaths at twilight, with snow dusting the front lawn and a pink sunset sky behind the building
    Historic brick Brampton 1860 inn decorated with Christmas lights and wreaths at twilight, with snow dusting the front lawn and a pink sunset sky behind the building Brampton 1860 offers the perfect retreat after a day at the festival | Photo: Better Living

    Staying at Brampton 1860 turned out to be the perfect pairing for Dickens of Christmas. After hours in the cold, I could retreat to my cottage just minutes away. It was also fun to see most of the guests in the Manor House “dressed like the dickens” throughout the weekend.

    On Saturday afternoon, I left the festival around 4 PM to make it back for tea time. Over Poinsettia cocktails and Chef Carol’s fresh-baked cookies in the Manor House, I talked through favorite moments from the day.

    Cozy library room at Brampton 1860 with floor-to-ceiling bookshelves, leather furniture, fireplace with burning fire, and large decorated Christmas tree with red ribbons
    Cozy library room at Brampton 1860 with floor-to-ceiling bookshelves, leather furniture, fireplace with burning fire, and large decorated Christmas tree with red ribbons The Manor House library at Brampton 1860 | Photo: Better Living

    The next morning at breakfast, guests traded stories of their time at Dickens – what they bought, what they ate, and their plans for next year. That shift from public celebration to private comfort gave the weekend a perfect rhythm.

    ➡ See our full Brampton 1860 review

    Why It Sticks With You

    Festival attendees in period costume sitting on antique Victorian couch and hay bales near firepit with bulldog wearing Christmas sweater in foreground
    Festival attendees in period costume sitting on antique Victorian couch and hay bales near firepit with bulldog wearing Christmas sweater in foreground Hay bales, firepits, and even sofas create casual gathering spots throughout the festival | Photo: Better Living

    I came for a Victorian festival and left talking about starting a new tradition.

    The logistics aren’t what linger. What stays with me is the feeling of a small town celebration that welcomes visitors into that experience.

    The costumes are fun. The food is comforting. The history is real. But it’s the warmth and ease of the community that makes the weekend feel meaningful.

    I’m already planning my return next year.

    🎄 Plan Your Trip: Dickens of a Christmas

    Woman in Victorian dress posing with Father Christmas character in decorative sleigh at night in front of Dickens of a Christmas festival banner
    Woman in Victorian dress posing with Father Christmas character in decorative sleigh at night in front of Dickens of a Christmas festival banner Victorian characters bring the festival to life throughout Historic Chestertown, MD | Photo: Better Living
    • Location: Downtown Chestertown, Maryland (High Street).
    • When: The first full weekend of December.
    • Cost: Free to attend. Bring cash for food vendors and the market.
    • Where to Stay: Brampton 1860 (Book well in advance, as this is a popular weekend).
    • Don’t Miss: The Carriage Rides and the Oyster Stew.

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • Holiday Magic and Winter Charm at Brampton 1860 – Chestertown, MD | Better Living

    Looking for the perfect winter getaway in Maryland? This Eastern Shore bed and breakfast transforms into a Victorian holiday wonderland each December, offering festive dinners, historic celebrations, and luxury accommodations just 2 hours from DC. Here’s our complete guide to Brampton 1860’s winter festivities and why it’s Maryland’s top-rated romantic inn for holiday escapes.

    🎄 BRAMPTON 1860 AT A GLANCE 🎄

    • Location: 25227 Chestertown Road, Chestertown, MD
      ▸ Scenic Eastern Shore setting
      ▸ About 2 hours from Baltimore or DC, 1 hour from Wilmington, DE
    • Vibe: Romantic, boutique luxury with a festive holiday atmosphere on a historic 35-acre estate
    • Price Range: $$–$$$ ($229–$450 depending on room and season)
    • Accommodations: Manor House rooms and private cottages featuring fireplaces, jetted tubs, and Japanese soaking tubs. Many rooms are decorated for the holidays in winter.
    • Dining: Farm-to-table three-course breakfast, afternoon tea, dinner for two, and curated partnerships with local restaurants
    • On-Site Winter Perks: 35 acres of gardens and trails, outdoor fire pit, Certified Wildlife Habitat, EV charging, resident chickens, and plenty of cozy common spaces
    • Awards & Recognition:
      • Select Registry member since 2001
      • National Register of Historic Places
      • Best Craft Lodging Property for the Mid-Atlantic Region (Select Registry)
      • Certified Wildlife Habitat
    • Best For: Romantic winter getaways, anniversaries, holiday escapes, history lovers, and nature enthusiasts
    • Reservations: BramptonInn.com or (410) 778-1860

    A Winter Getaway to Brampton 1860

    Brampton Manor House library decorated for Christmas with tall tree adorned with red and gold ribbons beside fireplace with lit fire, floor-to-ceiling bookshelves, brown leather furniture, oriental rug, warm yellow walls, reading lamps, cozy winter setting The Manor House library is a favorite gathering spot for winter reading and socializing | Photo: Better Living

    “This is exactly what the holidays should feel like.”

    My partner said, while we sat by the fireplace in our cottage, sipping hot cocoa and watching big snowflakes drift past the windows. We had just come back from hiking snowy trails, and the shift from cold air to a warm room made everything slow down in the most satisfying way. No rushing. No pressure to be anywhere. Just the sound of the fire, the soft glow of the Christmas tree, and that comfortable sense of being in the right place at the right time.

    That’s what winter at Brampton 1860 delivers. The historic Eastern Shore manor leans into the season with thoughtful touches that seem genuine. Fresh holiday cookies show up throughout the day. Eggnog pancakes make breakfast memorable. Piano music carries from the newly renovated salon where guests gather with wine. Outside, the property’s 35 acres are open for wandering, whether covered in snow or settling into the quiet of winter.

    The Holidays At Brampton 1860 and Chestertown, MD

    During our December stay, The Brampton Inn was fully booked, yet it maintained an intimate atmosphere. Some guests read in the library. Couples played board games by the fire. Others walked the snowy trails or sat on the porch watching the weather move across the property. Everyone seemed to find their own way to enjoy the season, which says a lot about how easy the place is to settle into.

    We spent three days here and filled them without trying. Hiking through fresh snow. Trying figgy pudding for the first time at a Victorian street festival. Building fires with the wood the inn leaves in each cottage. Seeing Squeaky, the black cat who always appears as breakfast is served. Sitting in the salon with Innkeepers Dave and Hilari and hearing stories about the inn’s long history.

    The Dickens of a Christmas celebration brought Victorian London to life in downtown Chestertown and was well worth the visit. But the moments that stayed with us happened back at Brampton. The quiet ones. The warm rooms. The sense that winter should be enjoyed instead of rushed through. The inn sets the tone for that kind of stay, and it lingers with you long after you leave.

    Arriving in Winter: Historic Chestertown Dressed for the Holidays

    Interior of Walnut & Wool boutique in Chestertown decorated for holidays, white vintage Christmas tree with ornaments, traditional green tree with lights, Tiffany-style pendant lamp, mannequin with bowler hat displaying scarves and accessories, vintage furniture, pressed tin ceiling
    Interior of Walnut & Wool boutique in Chestertown decorated for holidays, white vintage Christmas tree with ornaments, traditional green tree with lights, Tiffany-style pendant lamp, mannequin with bowler hat displaying scarves and accessories, vintage furniture, pressed tin ceiling Walnut & Wool boutique in charming downtown Chestertown, MD | Photo: Better Living

    We started our weekend in Historic Chestertown, MD – a four-minute drive from the Brampton Inn. The colonial river town had fully committed to the season, with Victorian-era decorations adorning every storefront and the anticipation of Dickens weekend building throughout downtown.

    The waterfront along the Chester River offered peaceful walking paths where winter’s crisp air replaced fall’s lingering warmth. While early December hadn’t brought significant snow yet, the town’s authentic charm and holiday spirit made it clear why people keep returning to this corner of the Eastern Shore for winter getaways.

    We strolled the quaint shops and historic streets, soaking in the small-town atmosphere before heading to Brampton 1860 for check-in and the beginning of our Victorian holiday adventure.

    Sunrise in the Garden Cottage: A Winter Haven

    Sunrise room at Brampton Garden Cottage showing king bed with white linens, brown leather loveseat and chair, blue walls, ceiling fan, air conditioning unit, warm lamps, hardwood floors, bathroom door visible, spacious 475 square foot accommodation
    Sunrise room at Brampton Garden Cottage showing king bed with white linens, brown leather loveseat and chair, blue walls, ceiling fan, air conditioning unit, warm lamps, hardwood floors, bathroom door visible, spacious 475 square foot accommodation
     The Sunrise in the Garden Cottage. Our cozy winter haven | Photo: Better Living

    Pulling into Brampton 1860, the inn’s entrance greeted us with evergreen wreaths, twinkling lights, and seasonal greenery. But the true magic awaited at the Sunrise in the Garden Cottage, where the room’s private entrance opened to reveal our own personal holiday retreat.

    Having visited Brampton during fall, we knew to expect exceptional accommodations. What we didn’t anticipate was how beautifully this room would embrace the winter season. A miniature Christmas tree glowed by the corner. The wood-burning fireplace was stocked and ready. The bathroom featured its own heater for added comfort.

    Elegant wreath with buffalo check ribbon, white frosted branches, and eucalyptus hanging on white door, Christmas tree visible through doorway in formal dining room beyond, holiday home decor
    Elegant wreath with buffalo check ribbon, white frosted branches, and eucalyptus hanging on white door, Christmas tree visible through doorway in formal dining room beyond, holiday home decor Stepping into our Sunrise in the Garden Cottage, decorated for the holidays, at Brampton 1860 | Photo: Better Living

    The Sunrise room measures 475 square feet with soaring 10-foot ceilings, offering ample space to truly settle in. The king-sized bed with its luxuriously comfortable linens became our evening sanctuary for Hallmark Christmas movie marathons by the light of our tree. The spacious sitting area provided an ideal spot for morning coffee and afternoon cocoa by the fireplace. The two-person garden tub and separate shower created a spa-like retreat after winter walks.

    Practical touches enhanced the experience: A mini-fridge for leftovers, an honor bar stocked with wine bottles and premade cocktails, and our own brick patio that offered views across the property to the Manor House. Everything had been considered.

     ➡  See our full Brampton 1860 review! 

    The Manor House: Where Holiday Spirit Comes Alive

    Brampton 1860 three-story brick Georgian manor house decorated for Christmas with evergreen wreaths, garland, and white lights on columned porch, dusted with fresh snow on lawn and brick walkway, warm window lights glowing against pink and purple sunset sky
    Brampton 1860 three-story brick Georgian manor house decorated for Christmas with evergreen wreaths, garland, and white lights on columned porch, dusted with fresh snow on lawn and brick walkway, warm window lights glowing against pink and purple sunset sky Brampton 1860 dressed for the holidays with a dusting of snow | Photo: Better Living

    After settling in, we walked the short path to the Manor House for afternoon tea. Before we even reached the door, Squeaky appeared – Brampton’s fourteen-year-old black cat who’s become a bit of a local legend. He greeted us warmly and led the way to teatime.

    Squeaky the black cat walking on brick steps at Brampton 1860, fourteen-year-old house cat with yellow-green eyes and tail raised, confident stride on red brick porch in winter
    Squeaky the black cat walking on brick steps at Brampton 1860, fourteen-year-old house cat with yellow-green eyes and tail raised, confident stride on red brick porch in winter Squeaky: Brampton’s legendary feline mascot | Photo: Better Living

    The Manor House had been transformed. Every room featured a fully decorated Christmas tree. Candles, wreaths, and poinsettias filled the historic spaces. Even the front and side porches showcased festive trees and decorations.

    Seeing the Brampton team again – Sarah, Donna, and Susan, along with owners Dave and Hilari, was wonderful. Their enthusiasm for the season creates an atmosphere where returning visitors are welcomed like family.

    During social hour, the staff shared details about the weekend’s festivities, including the Dickens celebration and the newly renovated Salon de Lumiere. Later that evening, we spent time with Dave and Hilari in the salon over wine, learning more about Brampton’s history and their exciting plans for the property’s future. Their passion for preservation and hospitality shines through in every conversation.

    Holiday tea time spread showing Christmas tree-shaped sugar cookies with green frosting and sprinkles, gingerbread cupcakes with whipped cream and gingerbread men, vegetable crudité platter with cherry tomatoes and cucumber ribbons, Jacob's Creek wine bottle, festive presentation on holiday plaid tablecloth
    Holiday tea time spread showing Christmas tree-shaped sugar cookies with green frosting and sprinkles, gingerbread cupcakes with whipped cream and gingerbread men, vegetable crudité platter with cherry tomatoes and cucumber ribbons, Jacob's Creek wine bottle, festive presentation on holiday plaid tablecloth Afternoon tea gets the holiday treatment at Brampton | Photo: Better Living

    The afternoon tea spread includes savory and sweet treats, fresh-baked cookies, coffee, tea, and complimentary red and white wine. On weekends, sparkling wine and festive cocktails like the Poinsettia (sparkling white wine with cranberry juice, garnished with fresh rosemary and cranberries) join the offerings.

    ➡ All of this is included with every room stay, making the value remarkable.

    The Salon de Lumiere: A New Gathering Space

    Brampton 1860 Salon de Lumiere decorated for Christmas with tall lit tree adorned with white poinsettias and red ornaments under crystal chandelier, brown leather club chairs at small round tables with festive cocktails, elegant botanical wallpaper, fireplace with evergreen garland and red ornaments, Tiffany-style lamps, warm ambient lighting in newly renovated gathering space
    Brampton 1860 Salon de Lumiere decorated for Christmas with tall lit tree adorned with white poinsettias and red ornaments under crystal chandelier, brown leather club chairs at small round tables with festive cocktails, elegant botanical wallpaper, fireplace with evergreen garland and red ornaments, Tiffany-style lamps, warm ambient lighting in newly renovated gathering space
     The newly renovated Salon de Lumiere: Brampton’s elegant gathering space | Photo: Better Living

    Among the most exciting additions to Brampton 1860 is the newly renovated Salon de Lumiere – the Room of Light. This refreshed space honors the manor’s historic charm while providing guests with a bright, welcoming place to gather and unwind. There’s also a new menu of festive holiday cocktails.

    Pink grapefruit cocktail in sugar-rimmed rocks glass garnished with blood orange wheel, rosemary sprig, and candied orange peel, surrounded by vintage Christmas ornaments on white surface
    Pink grapefruit cocktail in sugar-rimmed rocks glass garnished with blood orange wheel, rosemary sprig, and candied orange peel, surrounded by vintage Christmas ornaments on white surface Festive cocktails are now available at Salon de Lumiere at Brampton 1860 | Photo: Better Living

    On Friday evening, we experienced the salon’s warm ambiance firsthand. Local pianist Michael Casey played holiday classics from 3 PM to 6 PM, creating an ideal soundtrack for the festive atmosphere. The room glowed with soft lighting, and despite Brampton being completely booked for the weekend, the space accommodated everyone comfortably. Guests naturally flowed between the salon, the library, and the other common areas, each finding their preferred spot.

    Michael Casey playing red keyboard piano in Brampton's Salon de Lumiere during holiday social hour, guests seated in foreground watching performance, ornate bar with mirror and Christmas decorations in background, chandelier overhead, elegant patterned wallpaper
    Michael Casey playing red keyboard piano in Brampton's Salon de Lumiere during holiday social hour, guests seated in foreground watching performance, ornate bar with mirror and Christmas decorations in background, chandelier overhead, elegant patterned wallpaper Pianist Michael Casey playing holiday classics in the Salon de Lumiere | Photo: Better Living

    Throughout our stay, we witnessed this beautiful rhythm of guest activity. At all times of day and night, people were genuinely enjoying themselves in different ways. Some curled up with books in the library by the fireplace. Others gathered in the salon over wine and conversation. Couples stood on the porch watching snow fall. Guests strolled the property taking in the beautiful winter landscapes.

    The renovation maintained Brampton’s commitment to elegant comfort while making the space seem fresh and inviting. It’s become the heart of the Manor House during winter evenings, and we found ourselves returning here multiple times throughout our stay.

    Festive Brampton Breakfasts: Starting Winter Days Right

    Belgian waffle dusted with powdered sugar, garnished with yellow pansy flower, served with crispy bacon strips, fresh strawberry, fruit compote, maple syrup, and jam in white ceramic dishes, Christmas tree with colored lights blurred in background
    Belgian waffle dusted with powdered sugar, garnished with yellow pansy flower, served with crispy bacon strips, fresh strawberry, fruit compote, maple syrup, and jam in white ceramic dishes, Christmas tree with colored lights blurred in background Holiday waffles at Brampton 1860 | Photo: Better Living

    Breakfast is included at Brampton, and the winter menu got us into the holiday spirit. Each morning, Squeaky would show up at our door right on schedule – his internal clock is better than any alarm. Following him to the Manor House became one of our favorite rituals.

    The dining room was decorated for the season and made slow mornings even more relaxed. Chef Carol’s cooking was excellent throughout our stay. The eggnog pancakes were our favorite. They were light, well spiced, and tasted like a holiday treat without being overly sweet. The Belgian waffles and French toast looked great too. They came topped with rosemary sprigs, cranberries, and pomegranate seeds, which added a simple but seasonal touch.

    Locally Sourced and Handcrafted Selections That Change Daily

    Breakfast is served as a three course meal and starts with fresh coffee and a pastry, then a fruit bowl. Next is a full plate that includes the main dish along with bacon, potatoes, and eggs cooked any way you like. The breakfast selections change daily and the eggs even come from Brampton’s own chickens.

    Close-up of two heritage breed chickens at Brampton, black and white barred Plymouth Rock with prominent red comb in foreground, buff-colored hen behind, supplying fresh eggs for breakfast
    Close-up of two heritage breed chickens at Brampton, black and white barred Plymouth Rock with prominent red comb in foreground, buff-colored hen behind, supplying fresh eggs for breakfast Brampton’s chickens provide fresh eggs for breakfast each morning | Photo: Better Living

    We have stayed at plenty of places that offer a free breakfast, and Brampton is easily one of the most generous and consistent. Everything tastes fresh, is prepared with care, and the portions are substantial. You can even have breakfast delivered to your room, although we prefer visiting the main house.

    Assorted holiday cookies on decorative china plate including frosted Christmas tree sugar cookie with sprinkles, plain snowflake cookie, winter biscotti, served with Brampton-branded beverage in background
    Assorted holiday cookies on decorative china plate including frosted Christmas tree sugar cookie with sprinkles, plain snowflake cookie, winter biscotti, served with Brampton-branded beverage in background Chef Carol’s daily rotation of fresh-baked holiday cookies | Photo: Better Living

    Chef Carol also bakes holiday cookies every day. Snowflakes, Christmas trees, gingerbread men, winter biscotti, and snickerdoodles with sprinkles show up throughout the property. Each batch is fresh, and there’s always something new to try.

    What makes breakfast special is the relaxed vibe. Guests chat about yesterday’s adventures and swap plans for the day ahead. With a friendly staff who genuinely enjoy hosting, mornings here feel warm and welcoming.

    A Winter Hike Worth Remembering

    Woman in red puffy jacket and plaid scarf walking on snow-dusted woodland trail at Brampton 1860, bare winter trees with remaining green leaves arching overhead, snow covering ground and fallen leaves, peaceful winter hiking scene
    Woman in red puffy jacket and plaid scarf walking on snow-dusted woodland trail at Brampton 1860, bare winter trees with remaining green leaves arching overhead, snow covering ground and fallen leaves, peaceful winter hiking scene Exploring Brampton’s trails during our winter hike | Photo: Better Living

    On our second morning, we woke to something magical. Large, fluffy snowflakes were falling from the sky, dusting the 35-acre estate in white and creating the kind of winter scene that’s straight from a movie.

    After breakfast, we bundled up for a winter hike along Brampton’s well-maintained trails. The snow continued for hours, transforming familiar paths into something enchanted. The meadows looked pristine under a bit of snow, and the historic farm buildings took on a timeless quality that made it easy to imagine Brampton in the 1860’s.

    The trails here are accessible year-round and easy to navigate, with multiple spots to pause and take in the natural beauty. Even with snow on the ground, we were comfortable exploring, and the winter landscape revealed views we’d missed during our fall visit.

    Back at Sunrise in the Garden Cottage

    Person in Fair Isle sweater and red snowflake socks relaxing by fireplace holding Brampton-branded blue ceramic mug of hot chocolate topped with marshmallow, cozy winter scene with plaid blanket and warm fire
    Person in Fair Isle sweater and red snowflake socks relaxing by fireplace holding Brampton-branded blue ceramic mug of hot chocolate topped with marshmallow, cozy winter scene with plaid blanket and warm fire Hot cocoa by the fire: the perfect way to warm up after a winter hike | Photo: Better Living

    After our hike, we headed back to the Sunrise cottage. Brampton provides real wood for the fireplace and even builds the fire for you, so all you have to do is light it and keep it going. We spent the afternoon warming up by the fire and drinking hot cocoa. After being out in the cold, it was exactly what we needed.

    💡 TIP: The Manor House keeps cocoa available with homemade marshmallows and complimentary bottled water. Bring them back to your room and make hot cocoa whenever you want using your in-room, electric kettle.

    We settled into the sofa, mugs in hand, with nothing on the agenda except relaxing. Later that evening, we queued up a Hallmark Christmas movie, poured wine from the honor bar, and watched by the glow of our Christmas tree. These quiet moments, not on any itinerary, became some of our favorite memories from the weekend.

    This is what Brampton does especially well in winter. They create the framework for a holiday escape, then give you the space and comfort to actually unwind. There’s no pressure to constantly be doing something, just the freedom to enjoy the season at your own pace.

    Dinners for Two: Gourmet Convenience Without Leaving the Property

    Two individual seafood pot pies with golden flaky pastry crusts in ceramic dishes, served with mixed green salads, white wine in stemless glasses, crusty rolls, powdered sugar-dusted brownies, overhead table setting
    Two individual seafood pot pies with golden flaky pastry crusts in ceramic dishes, served with mixed green salads, white wine in stemless glasses, crusty rolls, powdered sugar-dusted brownies, overhead table setting The Delectable Seafood Pie – 1 of 3 “Dinners for Two” options | Photo: Better Living

    Among Brampton’s most valuable winter offerings is their homemade Dinners for Two. When restaurants in Chestertown close early and you want to stay cozy, these chef-prepared meals provide a convenient and delicious solution.

    During our stays, we’ve tried all three seasonal options, and each impressed us.

    Delectable Seafood Pie

    For seafood lovers, this dish delivers. The pie comes packed with fresh seafood in a creamy sauce under a flaky crust. It’s comfort food elevated, showcasing the Eastern Shore’s exceptional seafood. We ate this one in the Manor House dining room, enjoying the Christmas decorations and the company of other guests.

    Turkey (or Vegetarian) Chili

    The chili surprised us with its depth of flavor and well-balanced spice level. The turkey version stays lean while maintaining richness, and we heard from other guests that the vegetarian option is equally satisfying.

     💡 TIP: You can request shredded cheese and sour cream.

    Savory Beef Stew

    A rich bowl of hearty beef stew with a spoon next to a salad and glass of wine.
    A rich bowl of hearty beef stew with a spoon next to a salad and glass of wine. The Savory Beef Stew from Brampton 1860. Perfect with red wine and dining fireside in your cottage | Photo: Better Living

    The hearty and savory beef stew was ideal for winter evenings. Tender chunks of beef in a rich, flavorful base that’s been simmered to perfection. The generous portions easily serve two, and the meal arrives with mixed green salad, crusty bread for soaking up every drop, seasonal dessert (we enjoyed homemade brownies), and a complimentary bottle of red or white wine.

    Delivered in a charming picnic basket to our cottage, we ate by our fireplace while snow fell outside.

    All three dinners run $89-$99 and can be ordered when making your reservation. We highly recommend this option, especially for multiple-night stays. The convenience of having gourmet meals delivered to your room or served in the Manor House, combined with the quality and generous portions, makes it worthwhile.

    Dickens of a Christmas: A Victorian Holiday Celebration

    White draft horse pulling red holiday carriage with passengers through downtown Chestertown during Dickens festival, horse decorated with evergreen garland and red bow, bare winter trees and historic storefronts lining Main Street
    White draft horse pulling red holiday carriage with passengers through downtown Chestertown during Dickens festival, horse decorated with evergreen garland and red bow, bare winter trees and historic storefronts lining Main Street Complimentary carriage rides through historic Chestertown, sponsored by Brampton 1860 | Photo: Better Living

    As Saturday arrived, so did the main event: Chestertown’s annual Dickens of a Christmas celebration. This two-day Victorian Holiday Extravaganza transforms downtown into 1840s London, as Charles Dickens imagined the season.

    The festivities began Friday evening with beverage and food tents opening at 5 PM, followed by carriage rides from 6-8 PM. We participated in Fabulous First Friday, where downtown shops stayed open until 8 PM for holiday shopping with an evening of live entertainment.

    Saturday brought the full celebration. The streets of Chestertown filled with Victorian-costumed visitors, street performers, and holiday cheer. We enjoyed complimentary carriage rides through historic downtown (proudly sponsored by Brampton 1860), adding to the authentic period atmosphere.

    Food, Firepits, and Festive Treats

    Victorian-dressed couple in period costumes sitting on hay bales around small firepit at Dickens of a Christmas festival, woman in red velvet coat with top hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840s London atmosphere
    Victorian-dressed couple in period costumes sitting on hay bales around small firepit at Dickens of a Christmas festival, woman in red velvet coat with top hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840s London atmosphere Victorian London comes to life at Dickens of a Christmas in Chestertown, MD | Photo: Better Living

    The food vendor tents became our gathering spot for lunch. We ordered oyster stew from one of the local vendors, and the steaming cup of creamy, seafood-rich warmth hit the spot on a chilly December afternoon. Hay bales and firepits provided excellent spots to sit, eat, and soak in the atmosphere.

    For the first time, we tried figgy pudding, that mysterious Victorian dessert referenced in so many Christmas carols. The verdict? It’s actually more like a moist, spiced cake than a pudding, rich and satisfying with subtle fruit flavors. Worth trying for the novelty alone, and genuinely delicious.

    Saturday’s Victorian Celebration

    The Devil's Brigade performing on outdoor stage at Dickens of a Christmas, two musicians in cream sweaters playing guitar and bodhran drum, black backdrop with band logo, professional sound equipment, live music entertainment
    The Devil's Brigade performing on outdoor stage at Dickens of a Christmas, two musicians in cream sweaters playing guitar and bodhran drum, black backdrop with band logo, professional sound equipment, live music entertainment The Devil’s Brigade entertaining crowds at Dickens of a Christmas | Photo: Better Living

    Throughout the day, we explored Heritage Village, browsed the London Row Artisan Market, and enjoyed performances on the main stage. The Baltimore Pipe Band brought traditional music and The Devil’s Brigade returned for an afternoon set. The sense of community made the entire experience memorable.

    Chestertown Farmers Market: Winter Joy Every Saturday

    Chestertown Farmers Market on High Street filled with shoppers browsing vendor tents, bare winter trees overhead, colorful pop-up canopies lining closed street, crowds of people shopping local goods, community gathering atmosphere
    Chestertown Farmers Market on High Street filled with shoppers browsing vendor tents, bare winter trees overhead, colorful pop-up canopies lining closed street, crowds of people shopping local goods, community gathering atmosphere Chestertown Farmers Market buzzing with activity every Saturday morning | Photo: Better Living

    On Saturday morning before the Dickens festivities ramped up, we visited the Chestertown Farmers Market. Located in the 300 & 200 Block of High Street, the market runs year-round every Saturday from 8 AM to 12 PM, offering local produce, artisanal goods, and genuine community atmosphere.

    Two young goats on leash at Dickens petting zoo, orange and white spotted goat and black and tan kid goat resting on blanket, families and visitors in background at Chestertown Farmers Market
    Two young goats on leash at Dickens petting zoo, orange and white spotted goat and black and tan kid goat resting on blanket, families and visitors in background at Chestertown Farmers Market The petting zoo was a hit with visitors of all ages | Photo: Better Living

    For Dickens weekend, the market featured a special petting zoo that drew crowds of delighted visitors. Goats, chickens, ducks, therapy dogs, a Scottish Highland cow, and a miniature rooster filled the petting area. The instant joy on visitors’ faces as they interacted with these friendly animals reminded us why simple pleasures create lasting memories.

    Even without the Dickens additions, the farmers market provides another reason to visit Chestertown during winter. Combined with Brampton a four-minute drive away, it creates a weekend that balances activity with relaxation.

    Morning After: Savoring the Last Moments

    Holiday French toast breakfast plate with pomegranate seeds and fresh strawberries, served with champagne flute, fruit compote in glass dish, Christmas tree with multicolored lights in background, white china with blue floral pattern
    Holiday French toast breakfast plate with pomegranate seeds and fresh strawberries, served with champagne flute, fruit compote in glass dish, Christmas tree with multicolored lights in background, white china with blue floral pattern
     Festive French toast topped with pomegranate and fresh berries | Photo: Better Living

    Our final morning began with coffee by the fireplace followed by one last breakfast in the Manor House. The dining room conversation centered on favorite moments from the Dickens weekend, with guests already planning their return for next year.

    We took a final walk around the property, now peaceful after the weekend’s festivities. The Christmas decorations visible through Manor House windows and their warm glow made us appreciate every detail.

    Why Winter at Brampton Works So Well

    Brampton 1860 Manor House completely blanketed in heavy snow, three-story brick building with holiday lights outlining porch and roofline, evergreen wreaths on windows, snow-covered evergreen trees flanking property, warm yellow light glowing from windows in evening
    Brampton 1860 Manor House completely blanketed in heavy snow, three-story brick building with holiday lights outlining porch and roofline, evergreen wreaths on windows, snow-covered evergreen trees flanking property, warm yellow light glowing from windows in evening A true winter wonderland at Brampton 1860 | Photo: Hilari Rinehart

    We’ve visited Brampton across different seasons now, and winter is truly wonderful. The fireplace shifts from a cozy perk to something you look forward to all day. The private cottages become less like rooms and more like actual hideaways. Everything seems more intentional – the hot drinks, the warm spaces, the slower pace.

    What struck us most was how a completely booked weekend still maintained its intimate character. The property absorbed everyone gracefully. Some people reading by the fire in the library. Others having wine in the salon. Some on the porch watching the weather. A few out hiking. Everyone settled into their own peaceful rhythm.

    Here’s what sets Brampton apart: They’re so much more than an inn. They curate complete guest experiences. Want romance? They’ve got packages with champagne, truffles, roses, and candlelit dinners. Need wellness? Couples massages, yoga sessions, picnic lunches. Celebrating something? Celebration cakes, room upgrades, curated dining. It’s like having your own travel concierge who knows how to create the right getaway for what you need.

    Brampton 1860 staff and owners posing on brick front steps of white-columned Manor House porch, group of 11 people in navy blue Brampton polo shirts and casual attire, smiling team photo showing diverse staff members
    Brampton 1860 staff and owners posing on brick front steps of white-columned Manor House porch, group of 11 people in navy blue Brampton polo shirts and casual attire, smiling team photo showing diverse staff members The amazing team at Brampton 1860 | Photo: Brampton 1860

    The staff deserves special mention. Sarah, Donna, and Susan are warm, friendly, and helpful, and you notice how they keep everything running smoothly. They remember returning visitors and make it easy to settle in.

    Brampton works so well in winter because they understand that the best holiday memories usually happen in the quiet moments between the big events. Sharing an unhurried conversation, watching the weather change, or simply putting your phone down and being present.

    Planning Your Winter Visit to Brampton 1860

    Brampton 1860 Manor House illuminated at night during holidays with white string lights outlining porch columns and roofline, Christmas tree visible in lit window, bare winter trees silhouetted against dark blue twilight sky, brick walkway and landscaped grounds
    Brampton 1860 Manor House illuminated at night during holidays with white string lights outlining porch columns and roofline, Christmas tree visible in lit window, bare winter trees silhouetted against dark blue twilight sky, brick walkway and landscaped grounds Brampton aglow on a winter evening | Photo: Better Living

    The best time to experience Brampton during winter depends on what you’re seeking. Early December brings the Dickens of a Christmas celebration. Mid-December offers peak decorations and the Very Brampton 1860 Holiday package with live piano music. Late December features holiday celebrations and New Year’s packages for those seeking an intimate way to ring in 2026.

    The Sunrise in the Garden Cottage or Marley’s Cottage remain our top recommendations for their privacy, space, and cozy atmosphere enhanced by the fireplace and Christmas trees. Manor House rooms offer easy access to common areas and the newly renovated Salon de Lumiere is ideal for guests who want to maximize social time.

    When planning, check the Brampton 1860 event calendar first, then book your room and dining experiences together. The Dickens weekend sells out months in advance. Consider arriving early or staying late to fully enjoy the property without rushing.

    The Very Brampton 1860 Holiday Package

    Custom Brampton Inn 1860 Christmas ornament showing detailed illustration of three-story brick manor house with columned porch, blue ribbon banner, hanging on evergreen tree with red berry clusters and bokeh lights
    Custom Brampton Inn 1860 Christmas ornament showing detailed illustration of three-story brick manor house with columned porch, blue ribbon banner, hanging on evergreen tree with red berry clusters and bokeh lights A keepsake ornament from Brampton 1860 | Photo: Better Living

    For weekend stays between December 12, 2025 and January 4, 2026, Brampton offers their Very Brampton 1860 Holiday package. This exclusive retreat includes wine and live piano music Friday from 3-6 PM, festive treats at afternoon tea, complimentary in-room goodies like artisan chocolates and sparkling wine, gourmet breakfast each morning, and complimentary late check-out on Sunday.

    What makes this package special is the extra time to simply be. Sleep in on Sunday morning. Enjoy a leisurely final breakfast. Take one more walk around the snowy property. For those who can extend their stay, booking Sunday night saves 20% and adds another day of peaceful winter bliss.

    The Brampton 1860 Difference

    See also

    What keeps us coming back is simple. Brampton knows exactly what it is, and it does that very well.

    This is a carefully preserved 1860s manor where the innkeepers know your name, the owners are happy to sit down and talk about the property’s history, and afternoon tea includes wine and cocktails without extra charges. The Select Registry membership and National Register of Historic Places listing are nice credentials, but they mostly confirm what guests already feel. In 2025, Brampton was also awarded Best in Category for a Craft Lodging Property for the Mid-Atlantic Region by Select Registry, which felt well deserved.

    More than anything, they understand what actually matters to guests. Comfort. Quality. A sense of ease. You are welcomed, not processed. Even on a fully booked weekend, the place still feels calm and personal. You can spend the entire afternoon in your cottage and never feel like you are missing something.

    This is a different kind of luxury. Not flashy or overdone. It shows up in the details, the pacing, and the way the experience stays with you after you leave.

    Your Winter Escape Awaits

    Brampton-branded blue ceramic mug filled with hot chocolate topped with whipped marshmallow cream in foreground, person in plaid flannel blanket relaxing by roaring fireplace with orange and yellow flames
    Brampton-branded blue ceramic mug filled with hot chocolate topped with whipped marshmallow cream in foreground, person in plaid flannel blanket relaxing by roaring fireplace with orange and yellow flames Homemade hot cocoa kit provided in every cottage | Photo: Better Living

    Winter on Maryland’s Eastern Shore offers exactly what many people are looking for. Quiet beauty. Space to breathe. Seasonal celebrations if you want them, and plenty of solitude if you do not.

    Whether you are celebrating an anniversary, getting married, planning a romantic winter escape, or just need a few days away from modern life, Brampton 1860 is the place for you.

    Ready to Book Your Brampton 1860 Winter Getaway?

    Experience historic charm, private cottages with fireplaces, farm-to-table festive breakfasts, dinners for two, and serene Eastern Shore winter landscapes.

    Book Your Stay at Brampton 1860!

    Upcoming Winter Events at Brampton 1860

    Brampton’s seasonal calendar continues well beyond the Dickens celebration. Each event is designed with the same attention to detail, creativity, and warmth that defines winter at this historic inn. Here’s what’s coming up.

    Elegant Afternoon Tea

    January 25 and February 22, 2026
    2:00 PM to 3:30 PM
    $49 per person plus tax and gratuity

    A refined afternoon in the Manor House featuring curated teas and house-made treats.
    Gentle, quiet, and indulgent. Reserve by calling (410) 778-1860 to avoid additional platform fees.

    Dickens of a Christmas

    December 4 & 5, 2026

    Step back into 1840s London and experience the holiday season as Charles Dickens imagined it.
    This two-day Victorian Holiday Extravaganza includes entertainment, carriage rides, food vendors,
    beer and wine tents, street performers, live music, and more.

    Rooms for Dickens weekend sell out months in advance. Book early at BramptonInn.com to secure your
    accommodation for December 4 & 5, 2026.

    Grape Expectations: A Playful Plates Party” at Brampton 1860

    December 18, 2025
    6:00 PM to 8:00 PM

    At Brampton 1860, the holidays are celebrated with Joyeux Feast-ivités, a festive French-inspired dinner featuring small plates thoughtfully paired with French wines. The menu draws from classic French holiday gatherings, focusing on tradition, warmth, and good company. Nikki Sands from Breakthru Beverage Group will guide guests through each wine pairing throughout the evening. Space is limited.

    Price: $75 per person, plus $10 gratuity and tax
    Overnight guests receive 15% off Thursday night room rates

    Guests may book the dinner without reserving a room by purchasing tickets online or  call 410-778-1860 to avoid platform fees.

    Ring in the New Year at Brampton

    December 30, 2025 – January 1, 2026

    Experience an elegant getaway to ring in the New Year with the Cheers to New Years! Package.
    Choose either a 2-night or 3-night stay in one of the luxurious rooms. Sip champagne, savor an early
    New Year’s Eve dinner, enjoy a river cruise, and more. Start the new year with an intimate and elegant
    time away with the one you love.

    Winter Activities on Maryland’s Eastern Shore

    Beyond Brampton’s property and Chestertown’s charm, the Eastern Shore offers numerous winter activities:

    Fresh Oyster Season

    Winter brings peak oyster season to Maryland’s Eastern Shore. Sample them raw, stewed, fried, roasted, or baked at exceptional local restaurants:

    • The Retriever Bar and Oysters
    • Fish Whistle at the Granary in Georgetown
    • Blue Heron Oyster House in Rock Hall
    • Osprey Point in Rock Hall

    Outdoor Winter Adventures

    • Visit Adkins Arboretum in Tuckahoe State Park
    • Birdwatch at Eastern Neck National Wildlife Refuge, feeding ground for majestic Tundra Swans
    • Winter Walks at Eastern Neck – explore park areas not usually open to the public
    • Snowshoeing through winter landscapes when conditions allow
    • Scenic walks around Washington College

    Frequently Asked Questions About Winter at Brampton 1860

    When is the best time to visit Brampton during winter?

    Early December offers the Dickens of a Christmas celebration and peak holiday decorations. Mid-December through New Year’s provides the full festive experience with Christmas celebrations. Late November features the Ultimate Thanksgiving Getaway. Each timeframe offers unique experiences.

    Do I need to book dining experiences separately from my room?

    Yes. Special events like Grape Expectations and Christmas Dinner require separate reservations and often sell out quickly. The Dinners for Two can be ordered when making your room reservation and should be requested in advance. Book both accommodation and dining together for best availability.

    Is Brampton 1860 good for a romantic winter getaway?

    Absolutely. The cozy fireplaces, private cottages with Christmas trees, hot cocoa with homemade marshmallows, festive atmosphere, and intimate dining experiences make it ideal for couples seeking a romantic holiday escape.

    How far is Brampton from major cities?

    About 2 hours from Washington DC or Baltimore, and 1 hour from Wilmington, DE – an easy drive for a weekend winter escape or extended holiday stay.

    Are pets allowed at Brampton?

    Select cottages (Russell’s Cottage and Robin’s Nest) welcome pets. Book early as these rooms fill quickly, especially during the holiday season.

    What’s included in the room rate?

    Full gourmet breakfast daily with festive seasonal items, afternoon tea service at 4 PM with savory and sweet treats, complimentary wine and weekend sparkling wine, festive cocktails like the Poinsettia, fresh-baked cookies, access to all 35 acres of grounds, and use of common areas including fireplaces and the Salon de Lumiere.

    Can I visit just for events without staying overnight?

    Yes, most special events and dinners don’t require a stay. Some may be exclusively for overnight guests or welcome outside reservations based on availability. Contact Brampton 1860 directly at (410) 778-1860 for specific event policies.

    When should I book for Dickens of a Christmas weekend?

    Rooms sell out months in advance. For December 4 & 5, 2026, booking now is recommended to secure your preferred accommodation.

    Does it snow often in Chestertown?

    While snow isn’t guaranteed, December and January can bring beautiful dustings that transform the estate into a winter wonderland. Even without snow, the cozy fireplaces, festive decorations, and holiday atmosphere create an ideal winter retreat.

    Are the walking trails accessible in winter?

    Yes. The 35-acre property’s trails remain open and accessible year-round. They’re well-maintained and safe for winter walks, including light snow conditions. Dress warmly and wear appropriate footwear.

    Get Directions

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

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  • Christmas Light Displays in Wilmington Delaware

    Wilmington, Delaware transforms into a sparkling wonderland each December, with holiday experiences and dazzling Christmas light displays and that bring joy to families across the Brandywine Valley. Whether you’re searching for free neighborhood shows, immersive walk-through attractions, or family-friendly holiday events, Wilmington’s Christmas lights offer something magical for everyone.

    From the grand Holiday Magic at Riverfront in downtown Wilmington, to historic estates like Hagley these festive displays are the perfect way to celebrate the season. Finish your evening with a dinner at one of Wilmington’s most iconic restaurants like Bardea Food and Drink or the historic Hotel Dupont‘s Le Cavalier.  

    Now you can plan your visit to the best Christmas light experiences near Wilmington, DE with our complete guide for 2025.

     

    Holidays at Brandywine Museum of Art

    The Brandywine Museum of Art in Chadds Ford is a holiday tradition that blends art, history, and festive wonder. Since 1972, families returning for the iconic Brandywine Railroad every holiday season. This sprawling model train display has 2,000 feet of track and over 1,000 pieces.

    Towering trees and hand‑crafted ornaments fill the museum’s atrium, while seasonal exhibitions showcase local art. It’s the perfect mix of cultural and playful holiday spirit.

    When: Open daily 9:30 AM to 5 PM through Jan 4th; check the museum calendar for extended hours and special programming.
    Cost: $25 for adults; discounts for children, seniors; free for members.
    Where: 1 Hoffman’s Mill Rd, Chadds Ford, PA 19317
    Website: https://www.brandywine.org

     

    NOËL at Nemours Estate

    Known as “America’s Versailles,” the 77‑room Nemours Estate, which is brilliant during the holiday season. Once the home of Alfred I. duPont, you can explore the mansion, chauffeur’s garage, gardens and grounds at your own pace decorated with elegant trees, garlands, and festive lighting.

    For some night-time fun, stop in for live festive music, hot beverages, and firepits in the mansion Saturdays in December during extended evening hours. 

    Hours: Open throughout December with extended evening hours on select dates; check the calendar for special late‑night openings. CLOSED Christmas Eve and Christmas
    Cost: Tickets are $25 for adults; discounts available for children, seniors, and families.
    Where: 1600 Rockland Rd, Wilmington, DE 19803
    Website: https://www.nemoursestate.org

     

    Yuletide at Winterthur

    Each year the 1000 acre, 175-room Winterthur Museum, Garden & Library is transformed into a storybook holiday destination for Yuletide at Winterthur.

    This historic estate is decorated with sparkling trees. And holiday displays are inspired by beloved tales like “A Christmas Carol”, “Alice in Wonderland,” and “A Visit from St. Nicholas.”

    You’ll also encounter whimsical surprises like a gingerbread train station, a magical dollhouse, and toy trains. On select Friday or Saturday evenings, enjoy candlelit tours, cozy firepits, live music, festive cocktails, and seasonal treats served in their café.

    When: Open daily 10AM – 5PM through January 4; evening hours available on select nights
    Cost: Tickets are $30 for adults; discounts available for members, children, and seniors
    Where: 5105 Kennett Pike, Winterthur, DE 19735
    Website: https://www.winterthur.org

     

    Holidays at Hagley

    On 235 acres along the banks of the Brandywine River, the historic Hagley Museum and Library brings a perfect blend of history and tradition. Explore the Eleutherian Mills, the du Pont family’s first American home, decorated for the season in Colonial‑style. Don’t forget to check out their annual Gingerbread House Contest. It’s a chance to step back in time while enjoying festive cheer.

    On select nights, Holiday Nights Tours offer walks through the mansion, and light refreshments served in the giftshop afterward.

    Hours: Daily, 10 AM – 4 PM (closes 2pm Christmas Eve; closed Christmas Day)
    Cost: Tickets $20 for non-members
    Where: 298 Buck Rd, Wilmington, DE 19807
    Website: https://www.hagley.org

     

    Holiday Magic on the Christina Riverwalk

    For a festive stroll, head to downtown Wilmington where the Riverwalk is lit up making it a magical holiday backdrop.

    Stoll under cascades of lights and sparkling archways. The entire waterfront transforms into a whimsical walk‑through holiday display perfect for families and couples. The Riverwalk is open 7 days a week, and lights turn on at 5:00pm (dusk). On December 12th and 19th at 7 PM and New Year’s Eve at 6 PM don’t miss the holiday Drone Light Shows for something special.

    When: Daily; lights switch on at dusk and shine late into the evening.
    Where: Park at 601 S. Madison St, Wilmington, DE 19801
    Cost: Free
    Website: https://riverfrontwilm.com/holiday-magic

     

    Festival of Lights at Delaware Park

    With a stunning light display, the Festival of Lights make the perfect spot to snap holiday selfies. Then shop the holiday market and visit Santa for your annual family photo. This year, their giant party tent will be heated with plenty of cozy seating, and live entertainment.

    See also

    When: Friday & Saturday nights through December 20th, 4 – 9 PM
    Where: 777 Delaware Park Blvd., Wilmington, DE 19804
    Cost: Free (except pictures with Santa)
    Website: https://lightsatdelpark.com

     

    Winter Lights: Evening Concerts at Rockwood

    If you love music, celebrate the holidays in one of Wilmington’s most historic settings at the 19th‑century Rockwood Park & Museum. Enjoy free live musical concerts of holiday classics and then stroll through the mansion’s decorated halls while sipping refreshments from a cash bar.

    Cost: Free and family‑friendly.
    When: Friday, December 12th and 13th 6:00 – 9:00 PM
    Where: 4651 Washington Street Extension, Wilmington, DE 19809
    Website: https://www.newcastlede.gov

     

    Holiday Lights Express on the Wilmington & Western Railroad

    For a memorable experience, climb aboard a 100 year‑old, heated train coach, decked out in thousands of sparkling holiday lights. Then you’ll take a forty-five minute evening ride through the Red Clay Valley. Along the way enjoy the decorative displays of trackside neighbors, who deck out their homes and yards in lights.

    Rides run rain or shine and tend to sell out, so book your tickets early.

    Where: 2201 Newport Gap Pike, Wilmington, Delaware 19808
    When: Through December 31
    Cost: Tickets are $19 for adults and $17 for children 
    Website: https://wwrr.com

     

    A Longwood Christmas at Longwood Gardens

    Longwood Gardens becomes one of the region’s most spectacular holiday destinations.  Wander through themed conservatories sparkling with jewel‑toned displays, living wreaths, towering trees, reflection pools and horticultural artistry. Afterward, explore the gardens twinkling with more than 500,000 lights.

    Outdoors, glowing fountains dance to holiday music, and lighted tunnels invite visitors into immersive wonderlands. Minutes over the Pennsylvania border, it’s a blend of nature, design, and festive magic you won’t want to miss.

    When: Daily 10:00 am–11:00 PM
    Cost: Timed tickets required ($45); free for members; discounts for children and seniors.
    Where: 1001 Longwood Rd, Kennett Square, PA 19348
    Website: https://longwoodgardens.org

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

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  • City Weekends Are the New Wellness Getaways (Here’s How to Make Yours Count) | Better Living

    There was a time when “wellness” meant escaping to a cabin, booking a spa, or disappearing into a mountain retreat. But the truth is, most people don’t have the luxury of dropping everything for a week of silence and mineral water. What you do have is a city right in front of you, loud, layered, and surprisingly capable of giving you the exact reset you’ve been postponing.

    A well-planned city weekend can feel just as restorative as a traditional getaway, sometimes even more. You just need to know how to design it.

    Why Urban Wellness Weekends Are Having Their Moment

    Look, the modern wellness movement has finally caught up to reality. Not everyone can afford a week in Sedona. Not everyone wants to meditate in total silence. Some of us need the hum of life around us to actually relax.

    Cities offer something remote retreats can’t: options. Craving solitude? Find a hidden garden. Need energy? Step into the street festival happening three blocks over. It’s wellness with an escape hatch, and honestly, that’s what most of us need anyway.

    Slow Travel Principles That Still Work in Big Cities

    Slow travel isn’t about the size of the place. It’s about the pace you choose. In a big city, this often means resisting the pressure to treat your weekend like a checklist. Don’t sprint between landmarks. Don’t try to conquer a neighborhood in an hour. Instead, linger. Pick one district you’ve always rushed through and let yourself actually experience it.

    I learned this the hard way in Brooklyn last spring. Had a whole list of places to hit in Williamsburg. Made it to exactly two because I spent three hours in a used bookstore and then sat in McCarren Park watching dogs play. Best Saturday I’d had in months.

    The thing about slowing down: your nervous system literally recalibrates. City cafés become resting points. Bookstores become mini sanctuaries. A long walk becomes the whole activity.

    Want to keep this feeling going after the weekend? These easy ways to reduce stress work whether you’re home or exploring.

    Designing a Weekend That Actually Works

    Your weekend should feel like breathing, not sprinting. Movement, then pause. Here’s what I’ve figured out works: pick one or two anchor points. Maybe a morning market, maybe a museum, maybe checking out a top event venue that catches your eye. These give shape without becoming a death march of activities.

    But here’s the thing most people mess up: rest isn’t what you do with leftover time.

    Plan it. Actually put “sit in park for an hour” on your mental list. Book that long, lazy breakfast. Build in a full hour between neighborhoods just to wander. Sometimes the best thing you can do in a city is absolutely nothing, just in a different spot than usual.

    The Morning Thing

    Honestly, how you wake up on Saturday sets everything. Skip the grab-and-go coffee. Find somewhere that makes you want to stay. Somewhere with real chairs and windows and maybe plants that look like someone actually waters them.

    Start slow. Stretch in your hotel room. Walk without a destination for 20 minutes. Then find breakfast. Real breakfast. The kind where they refill your coffee without you asking and nobody’s rushing you out.

    This isn’t just feel-good advice. There’s something about breaking your usual morning pattern that signals to your brain: today is different. If you’re working on your healthy sleep routine, you already know how much those first morning moments matter.

    Where Atmosphere Becomes Part of the Self-Care Equation

    Here’s what nobody tells you: the spaces you choose do half the emotional work for you. There’s something about stepping from a loud street into a dim, warm bar that instantly slows your breathing. The right bar with warm lighting can slow your breathing. The right rooftop can make you feel bigger and lighter. Even the right street can change everything.

    This is why following your gut matters more than following guides. That coffee shop with the weird art and good light? Perfect. The hotel lobby that feels like someone’s living room? Stay there. The park bench with the view of nothing special but great people-watching? That’s your spot.

    Neighborhood Selection (Or: Don’t Go to Times Square)

    Not all neighborhoods are created equal for wellness weekends. You want the ones that feel lived-in, not performed. Skip the main drags. Find where locals actually hang out.

    Some neighborhoods just work better:

    • Arts districts usually have that creative lazy energy
    • Old residential areas with big trees feel grounding
    • Waterfront spots naturally calm people down
    • University areas blend energy with laid-back vibes

    Research, but not too much. Sometimes the best neighborhood is the one you stumble into.

    The Evening Reset

    Evenings are where the magic happens. Or where everything falls apart if you try to cram in too much.

    Stop activities by 8pm. Earlier if you can. Give yourself time to process the day. Find a wine bar with good light and journal. Walk along water if you can find it. Get back to your room with enough time to actually wind down.

    I know someone who always books hotels with good bathtubs for this exact reason. She calls it her “urban spa hour.” Smart.

    If nighttime anxiety is your thing, these ideas for how to calm your anxiety at night work just as well in hotels as at home.

    Seasonal Shifts

    Summer city weekends are entirely different animals than winter ones. Lean into it.

    Summer means rooftops, outdoor everything, late sunsets in parks. Winter means cozy bars, museums, bookshops, and really good coffee. Spring and fall are perfect for walking neighborhoods you’d usually drive through.

    Don’t fight the season. Work with it.

    Technology (Just Put It Down)

    You know what ruins an urban wellness weekend faster than anything? Instagram. Work emails. The constant need to document instead of experience.

    Set boundaries:

    • Photos at specific times only
    • Phone on airplane mode during meals
    • No laptops
    • Check messages once in the evening, maybe

    The city will still be there to photograph next time. This weekend is for you.

    Food as Part of It

    Your gut health affects everything, even on vacation. But this isn’t about restriction. It’s about choosing food that makes you feel good two hours later, not just while you’re eating it.

    Hit a farmers market Saturday morning. Find the restaurant using actual vegetables. Choose the bakery where things look homemade. And yeah, have the cocktail if you want it, but maybe also drink water.

    If you’re already thinking about gut health while traveling, you know the drill. But honestly, just eating sitting down instead of walking makes a huge difference.

    Solo vs. Together

    Both work. Depends what you need.

    See also

    Solo weekends let you be completely selfish with your time. Eat when you want. Rest when you want. Talk to strangers or don’t.

    Weekends with the right person can be incredible too, especially if you’re both on the same wavelength about pace. If you’re planning a couple’s weekend, cities like Philadelphia have tons of options.

    Groups get complicated. Keep them small.

    The Budget Reality

    You don’t need money to have an urban wellness weekend. You need intention.

    Free stuff that works:

    • Parks
    • Walking neighborhoods
    • People watching
    • Window shopping in fancy areas
    • Free museum days
    • Sunset watching from bridges

    Spend money on what matters to you. Maybe that’s one really good meal. Maybe it’s a massage. Maybe it’s the nice hotel room. Pick one thing to splurge on, keep the rest simple.

    Monday Morning Test

    If you did it right, Monday feels different. Not perfect, but different. You’ve got energy even though you didn’t “accomplish” anything. You see your regular routine with fresh eyes.

    That’s the whole point.

    Making This Regular

    Once you do one urban wellness weekend, you’ll want more. Good. Make them quarterly. Rotate between your city and nearby ones. Keep a running list of neighborhoods to explore and places to try.

    Some people do one weekend a month. Some do one per season. Figure out what works for you, but make it regular. Your sleep hygiene will thank you. Your stress levels will thank you. Your creativity will thank you.

    Regional Options Worth Considering

    Every region has cities perfect for this. In the Mid-Atlantic, you’ve got countless weekend getaways from Philadelphia. From DC, the day trip options work beautifully for quick urban resets.

    But honestly? Start with your own city. You probably haven’t seen half of it.

    Bringing It Home

    The real win is when elements from your wellness weekend sneak into regular life. That coffee shop you discovered becomes your Tuesday morning spot. The park you found becomes your lunch break walk. The neighborhood you explored becomes where you meet friends.

    This is how wellness becomes sustainable. Not through grand gestures, but through small shifts in how you move through the spaces you already inhabit.

    The Unexpected Power of Staying Close

    A city weekend isn’t a compromise. It’s a smarter version of a getaway, compact, energizing, and rooted in the idea that you don’t need distance to reset. You just need intention.

    Try this: Book a hotel in your own city for one night. Pick a neighborhood you never go to. Eat at restaurants you’ve never tried. Walk streets you usually drive. It’s shocking how different your own city feels when you’re a tourist in it.

    The streets are waiting. The cafés are open. Your urban wellness weekend starts the moment you decide to see your city not as a source of stress, but as a landscape for restoration. All it takes is choosing to move through it differently. Slower, softer, and with your wellbeing as the only agenda that matters.

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • Milford, PA: Your Perfect Fall Getaway in the Poconos | Better Living

    A fall getaway to Milford, PA guarantees more than stunning scenery: chase waterfalls, explore winding trails backdropped by autumn leaves, shop your way through a charming historic downtown, and linger over dinner in cozy historic taverns. This small Pennsylvania town deserves to be on your bucket list.

    Exploring Milford, Pennsylvania in the Fall

    Serene garden courtyard at historic Hotel Fauchere featuring ornate black Victorian fountain with flowing water, fall flowers, pumpkin decorations, yellow vintage beach cruiser bicycle for guests in downtown Milford Pennsylvania Hotel Fauchere’s serene garden courtyard features a flowing fountain and complimentary beach cruisers for exploring Milford | Photo: Better Living

    There aren’t many places where you can sip coffee in a famous Michelin-key hotel, discover Pennsylvania’s tallest waterfall, explore Gilded Age mansions, and eat in a restored 19th-century gristmill next to a 24-foot waterwheel all in an afternoon. In Milford, PA, you can.

    First settled in 1796 and known as the “Gateway to the Poconos,” Milford is the perfect blend of natural beauty, centuries-old charm, and small-town warmth. With a historic downtown featuring over 400 buildings on the National Register of Historic Places within a half mile, you can shop small, go antiquing, eat in cozy historic taverns, and discover museums housing some of America’s most important artifacts.

    Only 75 miles from NYC, Milford sits on the edge of the Delaware Water Gap National Recreation Area, hugged by the Delaware River where you can hike, bike, and kayak your way through over 70,000 glorious acres. With quick access to some of the most scenic trails and waterfalls in the Poconos, Milford’s location makes it one of the best day trips from Philadelphia for nature lovers.

    On our getaway here, we found fall brings out Milford’s best: crisp air, colorful foliage, cozy streets, and postcard-worthy views. If you’re planning a weekend getaway from Philadelphia, Milford should be at the top of your list. Here’s where we stayed, what we did, and what we ate while exploring this charming destination.

    Where to Stay in Milford, PA

    Milford’s boutique hotels and inns offer more than a place to rest – they’re part of the experience.

    Hotel Fauchère

    Historic Michelin Key Hotel Fauchere Victorian building illuminated at night with red and white striped awning, American flag, ornate white porch railings and vintage street lamps on Broad Street in downtown Milford Pennsylvania fall evening
    Historic Michelin Key Hotel Fauchere Victorian building illuminated at night with red and white striped awning, American flag, ornate white porch railings and vintage street lamps on Broad Street in downtown Milford Pennsylvania fall evening Hotel Fauchere’s iconic facade glows on a fall evening in downtown Milford | Photo: Better Living

    For luxury with a legacy, Milord’s famous Hotel Fauchere has been drawing travelers, notable figures and celebrities to Milford since the 1800s. And if you like quiet, historic boutique properties like we do, you’ll love it.

    In the heart of Milford’s historic district, it was first founded as a summer retreat and side hustle by Louis Fauchère in 1852, a Swiss born master chef who made a name for himself Delmonico’s, the US’s first fine dining restaurant in New York City. The first one to introduce fine dining to town.

    Recently awarded a prestigious Michelin key, Hotel Fauchere offers a relaxed and intimate retreat known for its elegant accommodations, personalized service, and its two fine dining restaurants – Bar Louis open for dinner and the Delmonico Room open for brunch on Sundays. The hotel’s current building, with a sweeping covered porch where you can relax with a book or dine ‌ in style, dates back to 1880.

    Guest relaxing on private balcony with gas firepit overlooking vibrant orange and yellow fall foliage trees at luxury boutique Hotel Fauchere in Milford Pennsylvania Pocono Mountains autumn getaway
    Guest relaxing on private balcony with gas firepit overlooking vibrant orange and yellow fall foliage trees at luxury boutique Hotel Fauchere in Milford Pennsylvania Pocono Mountains autumn getaway Unwind on your private balcony with a firepit and sweeping views of Milford’s autumn colors | Photo: Better Living

    And with only 16 cozy rooms and suites, this quiet property is the perfect place to recharge.

    The rooms here have lush modern comforts like plush beds, Carrera marble and Pennsylvania bluestone bathrooms, radiant-heated bathroom floors, Frette linens, and modern decor that elegantly blends with vintage accents.

    While meticulously restored with the hotel’s original grand historic charm, modern amenities like smart TV’s and free WIFI will keep you connected to the present.

    Some of our favorite features in our room were the Nespresso machine, the warming towel racks and our private balcony with a firepit. With a glass of wine, it was the coziest way to unwind on a fall evening.

    Outside the room, the sunlit library is the perfect spot for reading or doing a puzzle. Or head outside to their serene garden with flowing outdoor fountain, where complimentary yoga is offered to guests on Saturdays.

    Complimentary breakfast buffet plate with fluffy scrambled eggs, crispy bacon strips, breakfast sausage links, golden roasted breakfast potatoes, fresh croissant and fruit salad at boutique Hotel Fauchere Milford PA Poconos
    Complimentary breakfast buffet plate with fluffy scrambled eggs, crispy bacon strips, breakfast sausage links, golden roasted breakfast potatoes, fresh croissant and fruit salad at boutique Hotel Fauchere Milford PA Poconos Start your day with Hotel Fauchere’s complimentary breakfast buffet featuring eggs, pastries, and their famous homemade yogurt | Photo: Better Living

    Even night owls will love waking up here. Each morning, a complimentary buffet breakfast is served here daily with eggs, sausage, bacon, potatoes, fruit, and freshly baked croissants.

    A special treat we couldn’t get enough of is their homemade vanilla yogurt and granola. To get a caffeine fix, a coffee bar with Starbucks coffee is available for guests to enjoy throughout the day.

    For specialty coffee drinks like frappes, cappuccinos, pastries, scones, muffins and cafe fare, head next to their annex at 403 Broad Cafe next door. It’s a beautiful historic space to catch up on some work or fuel up for your next adventure.

    Then explore Milford on one of Hotel Fauchere’s beach cruisers available for guests. Whether you want to make an appointment at local spa or need a guide for a hike or a local recommendation, the concierge here will guide you in the right direction,

    La Posada

    Spacious Presidential Suite living room at La Posada boutique Mexican inn featuring colorful built-in window seat with vibrant pillows, vintage steamer trunks, mustard yellow leather chairs, sisal rug and eclectic decor in Milford Pike County Pennsylvania
    Spacious Presidential Suite living room at La Posada boutique Mexican inn featuring colorful built-in window seat with vibrant pillows, vintage steamer trunks, mustard yellow leather chairs, sisal rug and eclectic decor in Milford Pike County Pennsylvania La Posada’s Presidential Suite features two bedrooms, a full kitchen, and vibrant Mexican hospitality | Photo: Better Living

    La Posada offers something unexpected in Milford — a boutique inn and quiet escape that feels like a portal to Mexico in the Poconos.

    Housed in a lovingly restored 19th-century building, La Posada is an 11 room boutique property where Mexican hospitality meets small-town Pennsylvania charm.

    It’s intimate, stylish, and comfortable unfussy accommodation for a comfortable stay. And each room here is thoughtfully designed with handcrafted details, clean lines, modern furnishings and a palette that embraces Mexico’s warmth and vibrancy.

    Select suites have views of the Delaware River and offer king and queen beds with sleeper sofas. Other convenient amenities include free WIFI, smart TVs, bottled water, microwaves, mini fridges and room service when the onsite restaurant, Felix’s Cantina is open.

    For more space, consider booking their expansive Presidential suite with two bedrooms, a full kitchen, dining room, living room and reading nook with library. Guests are treated to a complimentary breakfast at Hotel Fauchere every morning.

    Whether you’re here for a romantic weekend, a culinary getaway, or a stroll through Milford’s historic downtown, La Posada invites you to slow down and stay awhile.

    Dining in Milford, PA: From Underground Speakeasies to Riverside Mill Restaurants

    Milford’s dining scene impressed us with its range of restaurants. From cozy historic taverns to sophisticated brasseries and authentic international cuisine. You won’t walk far without finding fresh gourmet coffee, and that’s definitely not a bad thing.

    Bar Louis: An Iconic Underground Brasserie

    Intimate underground speakeasy dining room at Bar Louis featuring black leather tufted banquettes, red velvet pillows, Andy Warhol celebrity photographs by Christopher Makos, and modern lighting in historic Hotel Fauchere Milford PA
    Intimate underground speakeasy dining room at Bar Louis featuring black leather tufted banquettes, red velvet pillows, Andy Warhol celebrity photographs by Christopher Makos, and modern lighting in historic Hotel Fauchere Milford PA Bar Louis’s sophisticated speakeasy atmosphere showcases rare Andy Warhol images by Christopher Makos | Photo: Better Living

    Dinner at Bar Louis, Hotel Fauchere’s underground fine dining brasserie, was a highlight of our trip. Accessed through an understated side entrance and down a flight of stairs, this sophisticated speakeasy transports you to another era.

    The gallery wall showcases notable hotel guests throughout history: Charlie Chaplin, Andrew Carnegie, JFK, Babe Ruth, Mae West, Sarah Bernhardt, both Presidents Roosevelt, and more. But the most iconic feature? Rare 1970s and 80s Andy Warhol images by his friend and collaborator, photographer Christopher Makos. Behind the bar hangs the rarest of them all: Andy Warhol kissing John Lennon. It’s a wonderful backdrop for enjoying their unique craft cocktails.

    Classic French escargot appetizer in Burgundy snail shells with garlic herb butter, grilled baguette toasts, and craft cocktail at Bar Louis underground brasserie in Hotel Fauchere Milford Pennsylvania
    Classic French escargot appetizer in Burgundy snail shells with garlic herb butter, grilled baguette toasts, and craft cocktail at Bar Louis underground brasserie in Hotel Fauchere Milford Pennsylvania Bar Louis’s classic Escargot arrives in Burgundy shells drenched in garlic herb butter | Photo: Better Living

    We visited on a Monday for Oyster Night – $1 raw or $2 roasted. We went for a half dozen roasted, and they were juicy, fresh, and delicious. For appetizers, the Escargot arrived in Burgundy shells drenched in garlic herb butter with grilled crouton. Our entree, the seared buttery Halibut in saffron broth with fingerling potatoes, creamy fava beans, asparagus, shaved fennel, and baby artichokes, was plated beautifully. The halibut was tender and rich. For dessert, Bar Louis’s refined Carrot Cake satisfied our sweet tooth with its moist, deeply spiced crumb.

    Bar Louis is open Thursday through Monday for dinner and Sunday brunch – a local favorite for date nights and celebrations.

    The Delmonico Room: Sunday Brunch Tradition

    Elegant intimate table for two in historic Delmonico Room restaurant with white tablecloth, vintage pastoral paintings on sage green patterned wallpaper and white wainscoting at Michelin Key Hotel Fauchere Milford Pennsylvania
    Elegant intimate table for two in historic Delmonico Room restaurant with white tablecloth, vintage pastoral paintings on sage green patterned wallpaper and white wainscoting at Michelin Key Hotel Fauchere Milford Pennsylvania The Delmonico Room at Hotel Fauchere offers Sunday brunch in an elegant Victorian setting | Photo: Better Living

    For a more formal experience, The Delmonico Room at Hotel Fauchere continues the property’s fine dining legacy. While we enjoyed the daily complimentary buffet breakfast during our stay, the Sunday brunch in this elegant dining room is a Milford tradition worth experiencing.

    Tom Quick Inn: Italian-American Comfort in a Victorian Landmark

    Sixty hour braised beef short ribs with creamy mashed potatoes, roasted Romanesco cauliflower, red wine demi glaze and crispy fried shallot strings served in cast iron skillet at historic Tom Quick Inn 1800s Victorian tavern in downtown Milford Pike County Pennsylvania
    Sixty hour braised beef short ribs with creamy mashed potatoes, roasted Romanesco cauliflower, red wine demi glaze and crispy fried shallot strings served in cast iron skillet at historic Tom Quick Inn 1800s Victorian tavern in downtown Milford Pike County Pennsylvania Tom Quick Inn’s signature sixty-hour braised short rib is comfort food perfection | Photo: Better Living

    For soul-warming Italian-American comfort food, we headed to Tom Quick Inn, just steps from Hotel Fauchere. This beautifully restored Victorian landmark, once an 1800s stagecoach stop, is now a culinary gem serving hearty plates and handmade pastas.

    Inside, dark woods, a large winding antique bar, chic vintage accents, and a fireplace create a cozy atmosphere. An unexpected feature? A large tropical fish tank. The outdoor veranda is a local favorite in warm weather, but we loved the intimate indoor setting.

    Standout dishes included the rich TQ Chowder, which blends Manhattan and New England styles, and the sixty-hour braised short rib served over creamy mashed potatoes with Romanesco cauliflower and red wine demi glaze. Crispy shallots added a welcome savory crunch.

    Don’t skip the craft cocktails. Our Passionfruit Mojito with rum, muddled mint, and lime juice was perfectly balanced. The warm hospitality here makes every meal feel special.

    Apple Valley Restaurant: Roadside Americana at Its Best

    Rustic barn interior at Apple Valley Restaurant showing exposed wooden beams, vintage Ito-Ga Feeds sign, antique wagon wheels, and cozy dining tables in Milford Pike County Pennsylvania
    Rustic barn interior at Apple Valley Restaurant showing exposed wooden beams, vintage Ito-Ga Feeds sign, antique wagon wheels, and cozy dining tables in Milford Pike County Pennsylvania Apple Valley’s charming barn-style interior features vintage Americana touches and Pocono hospitality | Photo: Better Living

    If you’re craving comfort food, quirky shops, and a little roadside nostalgia, Apple Valley Restaurant & Village Shops is your go-to stop. Just off Route 6 and across from Grey Towers, this restaurant and mini-village modeled after Peddler’s Village in Bucks County, blends Americana charm with Pocono hospitality, making it a favorite for locals and tourists since 1966. And we love it.

    Open for lunch and dinner daily with a full bar, Apple Valley serves hearty American comfort food like blooming onions, nachos, brisket, fajitas, and burgers, with seasonal surprises like Oktoberfest specials bringing schnitzel and bratwurst to the table.

    Loaded appetizer nachos with melted cheddar cheese, jalapeños, tomatoes, black olives and sour cream being lifted with cheese pull at Apple Valley Restaurant in Milford, Pennsylvania Pocono Mountains
    Loaded appetizer nachos with melted cheddar cheese, jalapeños, tomatoes, black olives and sour cream being lifted with cheese pull at Apple Valley Restaurant in Milford, Pennsylvania Pocono Mountains The shareable nachos at Apple Valley are piled high with flavor | Photo: Better Living

    We couldn’t resist the savory mushroom Brie soup and the Valley Sampler Platter with chicken and lemongrass pot stickers, deep-fried mozzarella moons, and buffalo chicken tenders served with teriyaki, marinara, and bleu cheese sauces – great for sharing. For dessert, the Brownie Bomb is unbeatable: a warm chocolate chip-filled brownie topped with peanut butter ice cream, fresh whipped cream, candied walnuts, chocolate syrup, and peanut butter sauce.

    After your meal, wander through the cottage-style shops to browse handmade gifts, Christmas ornaments, outdoor gear, and candy. The grounds feature apple trees, koi ponds, a restored 1800s schoolhouse, and picnic tables for relaxing.

    The Waterwheel Cafe: Dining Beside History

    Historic 19th century three-story wooden waterwheel machinery and gears built by Fitz Water Wheel Company Hanover PA inside restored grist mill at The Waterwheel Cafe on National Register of Historic Places in Milford Pennsylvania
    Historic 19th century three-story wooden waterwheel machinery and gears built by Fitz Water Wheel Company Hanover PA inside restored grist mill at The Waterwheel Cafe on National Register of Historic Places in Milford Pennsylvania The Waterwheel Cafe’s fully functional three-story waterwheel is listed on the National Register of Historic Places | Photo: Better Living

    The Waterwheel Café, Bakery and Bar offers one of Milford’s most unique dining experiences. Here you can enjoy American, French, and Vietnamese comfort food while dining beside a fully restored, three-story-high 19th-century waterwheel listed on the National Register of Historic Places.

    Vietnamese rice noodle salad bowl with sliced grilled herb chicken breast, fresh cucumber slices, julienned carrots, crispy crushed peanuts, fresh lemon wedge and lettuce being twirled on fork showing noodle texture at The Waterwheel Cafe bakery bar in restored 19th century grist mill listed on National Register of Historic Places Milford Pike County Pennsylvania Pocono Mountains
    Vietnamese rice noodle salad bowl with sliced grilled herb chicken breast, fresh cucumber slices, julienned carrots, crispy crushed peanuts, fresh lemon wedge and lettuce being twirled on fork showing noodle texture at The Waterwheel Cafe bakery bar in restored 19th century grist mill listed on National Register of Historic Places Milford Pike County Pennsylvania Pocono Mountains The Waterwheel Cafe blends American, French, and Vietnamese flavors in dishes like their fresh rice noodle salad | Photo: Better Living

    Through the glass window in the dining room, you’ll watch the fully functional waterwheel turn while enjoying dishes like tempura soft shell crab wraps, bánh mìs, open-faced brie melts, Cubanos, croissant sandwiches, and rice noodle salads. When weather permits, the deck overlooking peaceful Sawkill Creek is the place to be.

    The bakery is a destination in itself, with freshly baked scones, pain au chocolat, and rotating pies. The mixed fruit and berry pie is a standout. Before leaving, browse the connected country store filled with antiques and vintage finds, then take a self-guided tour of the mill and waterwheel.

    Felix’s Cantina: Authentic Yucatán in Pennsylvania

    Taco Tuesday special featuring cochinita pibil tacos on handmade tortillas with guava margarita cocktail with Tajin rim, tortilla chips, fresh guacamole and salsa at authentic Mexican restaurant Felix's Cantina in Milford Pike County Pennsylvania
    Taco Tuesday special featuring cochinita pibil tacos on handmade tortillas with guava margarita cocktail with Tajin rim, tortilla chips, fresh guacamole and salsa at authentic Mexican restaurant Felix's Cantina in Milford Pike County Pennsylvania Taco Tuesday at Felix’s Cantina features authentic Yucatán flavors and build-your-own margaritas | Photo: Better Living

    For truly authentic Mexican cuisine, Felix’s Cantina on the ground floor of La Posada exceeded all expectations. The menu features Yucatán dishes made from family recipes—queso fundido, ceviche, arrachera, whole fried snapper, chicken mole, and tres leches cake served in a space that transports you to the Yucatan Peninsula.

    Lucky to visit on Taco Tuesday, we were blown away by the fresh, authentic flavors. Standouts were the cochinita pibil tacos and flash-fried Puffy Chicken Tacos made with handmade corn tortillas topped with lettuce, grilled marinated chicken, tomato, avocado, and pickled onions.

    Authentic Mexican puffy chicken tacos with crispy fried handmade corn tortillas topped with shredded lettuce, grilled chicken, diced tomatoes, avocado slices and bright pink pickled onions at Felix's Cantina La Posada Milford Pennsylvania
    Authentic Mexican puffy chicken tacos with crispy fried handmade corn tortillas topped with shredded lettuce, grilled chicken, diced tomatoes, avocado slices and bright pink pickled onions at Felix's Cantina La Posada Milford Pennsylvania Flash-fried Puffy Chicken Tacos with handmade tortillas are a Tuesday night favorite at Felix’s Cantina | Photo: Better Living

    We built our own margarita with guava and a Tajin rim – a refreshing complement to our meal. If you’re a fan of rare or small-batch tequilas, Felix’s shelves are stocked with hard-to-find bottles you won’t see in big-box stores.

    With colorful décor, warm hospitality, and a menu inviting exploration, Felix’s was one of our favorite stops in Milford. Felix’s is closed Wednesdays and Thursdays, but don’t miss Margarita Mondays or Taco Tuesdays for dining and drink specials.

    More Milford Dining Worth Exploring

    The Social (224a Broad St) serves outstanding casual Italian, pizza, and small plates. We devoured a Shrimp Parmigiana Hero and Sausage Pizza with fresh, tangy sauce, mildly spicy sausage, and a light and chewy crust with a crisp edge. With only a handful of tables, it fills quickly during peak hours. It’s BYOB, so grab a bottle from Milford Wine and Cheese Co a few doors down.

    Historic Dimmick Inn (101 E Harford St) is one of Pennsylvania’s oldest pubs, originally built by Samuel Dimmick in 1828. Recently restored with three dining rooms, a fireplace, and a renovated bar decorated with vintage finds and local art, it’s known for hearty American fare and award-winning French Onion Mac and Cheese. We loved their giant Bavarian beer pretzel served with creamy Yuengling buttermilk cheese sauce. The wood-fired Fig and Pig pizza, topped with fresh mozzarella, whipped ricotta, fig, pancetta, hot honey drizzle, and arugula was sweet, savory, and spicy.

    Milford, PA Things To Do: Waterfalls, Mansions, and Hidden Parks

    Raymondskill Falls: Pennsylvania’s Tallest Waterfall

    Woman viewing Pennsylvania's tallest waterfall Raymondskill Falls from wooden observation platform showing three tiers of cascading water at 178 feet surrounded by autumn forest foliage in Delaware Water Gap National Recreation Area near Milford PA
    Woman viewing Pennsylvania's tallest waterfall Raymondskill Falls from wooden observation platform showing three tiers of cascading water at 178 feet surrounded by autumn forest foliage in Delaware Water Gap National Recreation Area near Milford PA At 178 feet tall, Raymondskill Falls is Pennsylvania’s tallest waterfall and just 4 miles from downtown Milford | Photo: Better Living

    For a magical experience, visit Pennsylvania’s tallest waterfall, Raymondskill Falls, just 4 miles from downtown Milford. A 5-minute walk on an easy, beginner-friendly trail (about 0.3 miles) leads to one of the region’s most beautiful natural wonders. At 178 feet tall, it’s only a few feet shorter than Niagara Falls.

    Raymondskill Falls has two viewing platforms—one near the top looking down on the falls and one placing you at the center of the waterfall’s three cascades. For the best view, head to the lower platform. Best of all, it’s free. This waterfall is especially stunning in fall when surrounded by colorful foliage—making it a highlight of any fall foliage road trip of the Northeast.

    Tip: Wear shoes with good grip as some trail parts can be slippery when wet. Park at the first of two parking lots for direct access to the lower platform. Weekends can be busy, but on our early weekday visit, we encountered only a handful of people.

    Grey Towers: The Birthplace of American Conservation

    French chateau style Grey Towers National Historic Site mansion with stone turrets, ivy covered walls, manicured lawn, fall foliage and pumpkin decorations, former home of Gifford Pinchot in Milford Pennsylvania Pocono Mountains
    French chateau style Grey Towers National Historic Site mansion with stone turrets, ivy covered walls, manicured lawn, fall foliage and pumpkin decorations, former home of Gifford Pinchot in Milford Pennsylvania Pocono Mountains Grey Towers National Historic Site, the birthplace of American conservation, showcases stunning French chateau architecture | Photo: Better Living

    Just outside downtown, Grey Towers is a Gilded Age mansion and National Historic Site considered the birthplace of American conservation and one of Milford’s most impressive attractions.

    Built in 1886 by wealthy wallpaper merchant and philanthropist James Pinchot, this French chateau-inspired estate later became home to his son, Gifford Pinchot. Gifford became the first Chief of the U.S. Forest Service, appointed by Theodore Roosevelt in 1905, and a two-term Governor of Pennsylvania. He believed that “without abundant resources, prosperity is out of reach” and that managing forests was for “the greatest good for the greatest number in the long run.”

    See also

    This 102-acre estate became a gathering place for conservationists and politicians whose discussions shaped early U.S. environmental policy. Today you can tour the architectural grandeur of this estate with its fairytale turrets, sweeping mountain views, manicured gardens, seasonal blooms, and shaded trails. The grounds are open to cars and pedestrians from sunup to sundown year-round.

    Self-guided home tours are available, but check the website before you go for hours and updates, especially during holidays and government shutdowns.

    Milford Beach: River Access and Scenic Trails

    Scenic Delaware River shoreline at Milford Beach in autumn showing peaceful sandy beach, calm blue water, forested hillsides with fall foliage colors and pedestrian bridge, part of Delaware Water Gap National Recreation Area Pennsylvania
    Scenic Delaware River shoreline at Milford Beach in autumn showing peaceful sandy beach, calm blue water, forested hillsides with fall foliage colors and pedestrian bridge, part of Delaware Water Gap National Recreation Area Pennsylvania Milford Beach offers peaceful riverside walks and access to the 37-mile McDade Recreational Trail | Photo: Better Living

    With a launch site for canoes and kayaks, Milford Beach is a popular spot for swimming, paddling, picnicking, and exploring trails minutes from downtown. Open year-round, you can walk along the beach or access the northern gateway of the 37-mile McDade Recreational Trail running the length of the Delaware Water Gap National Recreation Area.

    The trail offers stunning views of the Delaware River, forests, fields, and passes old homesteads, canal locks, and colonial-era landscapes. It’s excellent for birding and seeing wildlife like bald eagles, herons, and deer. In winter, the trail becomes a snowy corridor for cross-country skiing.

    In the off-season, there’s no entrance fee and you’ll have it all to yourself – great for a picnic or a peaceful beach walk.

    Ethel Barckley Memorial Park: A Hidden Overlook

    Peaceful Delaware River shoreline at Milford Beach Pennsylvania in autumn showing rocky pebble beach, calm blue water, green steel pedestrian truss bridge, forested hillsides with orange and yellow fall foliage, clear blue sky, northern gateway to 37-mile McDade Recreational Trail in Delaware Water Gap National Recreation Area Pike County
    Peaceful Delaware River shoreline at Milford Beach Pennsylvania in autumn showing rocky pebble beach, calm blue water, green steel pedestrian truss bridge, forested hillsides with orange and yellow fall foliage, clear blue sky, northern gateway to 37-mile McDade Recreational Trail in Delaware Water Gap National Recreation Area Pike County Milford Beach offers peaceful riverside walks and access to the 37-mile McDade Recreational Trail | Photo: Better Living

    For a hidden gem with stunning high-up panoramic views of the Delaware River, stop at tiny Ethel Barckley Memorial Park. This pocket park is dedicated to notable Milford resident Ethel Barckley, a landscape artist named Pike County Woman of the Year in 1954, founding member of the Milford Garden Club, and first secretary of the Pike County Historical Society.

    With a swing and a bell that chimes with strong winds, it’s a peaceful spot for a short rest, just steps from downtown. We discovered this gem before eating at Felix’s Cantina at La Posada, which is across the street.

    The Columns Museum: Standing Inches from History

    At The Columns Museum, you’ll stand inches from one of the most haunting relics in American history inside a 1904 Neo-Classical mansion. Explore this historic 22-room mansion to find the blood-stained flag that cradled Abraham Lincoln’s head the night he was assassinated, along with Pike County’s most fascinating artifacts including a restored 1850s stagecoach, Civil War memorabilia, vintage fashion, rare photographs, and more.

    Curated by the Pike County Historical Society, the exhibits honor the people and stories that shaped this corner of Pennsylvania, including the indigenous Lenape tribes who lived here.

    Visitor Tip: The museum is typically open Wednesday through Sunday, with a modest admission fee supporting local preservation efforts. Guided tours are available and well worth it for the deeper stories behind the artifacts.

    Shopping Downtown Milford

    Charming historic downtown Milford Pennsylvania Broad Street in autumn showing boutique shops, orange pumpkins, burgundy mums in planters, tree-lined brick sidewalk, Pike County Place sign, and fall decorations in Gateway to the Poconos
    Charming historic downtown Milford Pennsylvania Broad Street in autumn showing boutique shops, orange pumpkins, burgundy mums in planters, tree-lined brick sidewalk, Pike County Place sign, and fall decorations in Gateway to the Poconos Downtown Milford’s walkable half-square-mile features over 400 buildings on the National Register of Historic Places | Photo: Better Living

    Explore Milford’s charming blend of boutique finds, artisan goods, vintage treasures, and locally made gifts in a walkable half-square-mile downtown.

    Don’t miss Willow (317 Broad St), a beautiful eclectic shop with vintage and modern wares where you can browse unique gifts, home decor, clothing, and cards. For treasure hunting, visit Old Lumberyard Antiques, where over 40 vendors offer their unique finds.

    For an organic espresso bar, bakehouse, cafe, juice bar, and bookstore with community spirit, check out Better World (322 Broad St #2). Enjoy great coffee, sourdough, and gluten-free treats while browsing curated books, puzzles, toys, and unique gifts like grow-your-own kits and essential oils promoting sustainable living.

    If you love charming shopping villages, you’ll also want to explore Peddlers Village, another beloved Pennsylvania destination about 90 minutes from Milford.

    Milford’s Vibrant Festivals

    Milford hosts vibrant festivals celebrating music, film, and storytelling throughout the year. In June, the Milford Music Festival fills the streets with live performances and local energy. For literary lovers, the Milford Reader and Writers Festival offers readings, panels, and conversations with both local and nationally acclaimed authors. Past guests have included Pulitzer Prize winners and New York Times bestsellers. October brings the Black Bear Film Festival held at the historic 1920s Milford Theater, showcasing indie films in an intimate setting.

    Getting to Milford, Pennsylvania

    Milford sits right near the borders of New York and New Jersey in northeastern Pennsylvania, making it a quick tri-state gateway. Nestled along the Delaware River, it’s easily accessible from major cities.

    From New York City (~75 miles / 1.5–2 hours): Take I-80 W or I-84 W to US-6 W

    From Philadelphia (~120 miles / 2.5 hours): Take I-476 N to I-80 W, then US-209 N

    From Allentown, PA (~70 miles / 1.5 hours): Take PA-33 N to US-209 N

    From Washington, DC (~3 hours): Milford also makes a great day trip from Washington DC for those looking to escape the city for natural beauty and small-town charm.

    Public Transit: From NYC, take the Metro-North Port Jervis Line to Port Jervis, NY, then a short taxi or rideshare to Milford.

    Final Thoughts

    Fallen autumn leaves covering sidewalk illuminated by vintage street lamps along tree-lined residential streets in historic downtown Milford Pennsylvania at dusk with golden and orange foliage on trees
    Fallen autumn leaves covering sidewalk illuminated by vintage street lamps along tree-lined residential streets in historic downtown Milford Pennsylvania at dusk with golden and orange foliage on trees Milford’s historic downtown transforms into a magical autumn scene after dark | Photo: Better Living

    Milford is the perfect blend of natural beauty, centuries-old charm, and small-town warmth. Like stepping into a postcard from the past, it’s exactly what you want from small-town travel. Whether you’re looking for outdoor adventure or an upscale hideaway, Milford PA is worth the drive.

    On our fall getaway, we found Milford brings out the best: crisp air, colorful foliage, cozy streets, and postcard-worthy views. From sipping morning coffee at a Michelin-key hotel to standing beneath Pennsylvania’s tallest waterfall, from exploring the birthplace of American conservation to savoring authentic Yucatán tacos in a boutique inn, Milford offers experiences you won’t find anywhere else.

    With a historic downtown where over 400 buildings grace the National Register of Historic Places within a half mile, quick access to over 70,000 acres of the Delaware Water Gap National Recreation Area, and a dining scene that punches well above its weight, Milford deserves its reputation as the Gateway to the Poconos.

    Whether you’re here for a day or a weekend, this charming Pennsylvania town will leave you refreshed and inspired—and already planning your return visit. For more Pennsylvania getaway ideas, explore our guides to Gettysburg, Nemacolin Resort, Glasbern Inn, Downtown Lancaster, and our Southeast Pennsylvania’s foodie road trip.

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • Things to Do in Chestertown MD: Eastern Shore Travel Guide | Better Living

    Want to step into a living postcard? Chestertown, Maryland, has everything you want in a small coastal town: walkable historic streets, friendly people, unique eateries and indie shops that feel more like treasure hunts than retail.

    Historic Chestertown Maryland

    Scenic view of the Chester River waterfront in Chestertown, Maryland, framed by overhanging tree branches with bright green leaves. A wooden park bench with ornate cast iron arms sits on a brick paver walkway in the foreground. Natural landscaping with ornamental grasses and rocks lines the water's edge. In the middle distance, a historic tall ship with two masts is docked at a wooden pier alongside modern sailboats. The river stretches wide under a brilliant blue sky filled with puffy white clouds, with tree-lined shores visible on the opposite bank. Peaceful waterfront views along the Chester River in Chestertown, MD. with maritime charm on full display | Photo: Better Living

    Chestertown has a permanent spot on our must-visit list.

    Nestled along the Chester River, Chestertown, on Maryland’s Eastern Shore, may be off the beaten path, but that’s exactly what makes it so special. With big character and historic colonial charm, this unique small town may be one of America’s coolest under-the-radar destinations.

    Once an important port city founded in 1706 and nestled along the banks of the Chester River, today you can walk through peaceful brick-lined streets lined with 18th-century homes, visit historic landmarks, and shop your way through a town that feels like it was decorated for a Hallmark movie set. Except this one is real.

    Chestertown’s downtown and historic district, listed on the National Register of Historic Places, is home to Washington College, the first college chartered in the United States in 1782.

    This friendly town is full of character. And there’s plenty to do within a few square blocks. Looking for more Maryland Eastern Shore destinations? Explore nearby St. Michaels, MD and Kent Narrows.

    Things to Do in Chestertown MD

    Ornate Victorian-era fountain painted in turquoise blue located in a town square in Chestertown, Maryland. The multi-tiered cast iron fountain features elaborate scrollwork, decorative flourishes, and a female figure statue at the top. Water flows from multiple levels into a circular basin below. The fountain sits on brick pavement surrounded by a green lawn, with mature trees providing dappled shade. Historic buildings and parked cars are visible in the background under a clear blue sky.
    Ornate Victorian-era fountain painted in turquoise blue located in a town square in Chestertown, Maryland. The multi-tiered cast iron fountain features elaborate scrollwork, decorative flourishes, and a female figure statue at the top. Water flows from multiple levels into a circular basin below. The fountain sits on brick pavement surrounded by a green lawn, with mature trees providing dappled shade. Historic buildings and parked cars are visible in the background under a clear blue sky. The iconic Hebe fountain in downtown Chestertown – a perfect spot to rest while exploring the historic district | Photo: Better Living

    Explore Historic Fountain Park

    Start your day at Chestertown’s small but beautiful Fountain Park at the intersection of High and Cross Streets in the heart of town. A gathering place throughout the year, it’s also home to the Hebe Fountain, one of Chestertown’s iconic historic landmarks.

    A symbol of the town’s timeless charm, it’s one of the many public art installations throughout the town.

    Installed in 1899, made of cast iron, painted turquoise, and fully functional, you can’t miss it. Decorated beautifully with carved lions and swans, its standout feature is the Greek goddess of youth, Hebe, who pours “ambrosia” into a chalice at the fountain’s top.

    Visit the Chestertown Farmers Market

    Every Saturday from 8 to noon, here you’ll find the year-round Chestertown Farmers Market, where you can shop for local fresh produce, eggs, meat, dairy, flowers, baked goods, and artisan crafts.

    Stroll the Historic Waterfront

    White wooden boardwalk pier extending over Chester River with gray railings on both sides, blue sky with white clouds, marina dock with boats visible in background, trees lining waterfront, peaceful water scene
    White wooden boardwalk pier extending over Chester River with gray railings on both sides, blue sky with white clouds, marina dock with boats visible in background, trees lining waterfront, peaceful water scene Stroll Chestertown’s peaceful waterfront boardwalk along the Chester River | Photo: Better Living

    If you’re visiting Chestertown for the first time, don’t miss the chance to stroll along its historic waterfront where you can enjoy shaded benches, river views, and a quiet place to relax with coffee or a picnic. It’s a popular birdwatching spot where ospreys, hooded mergansers, great blue herons, and other native birds make regular appearances.

    Docked at the Chestertown Marina, you can also see the Schooner Sultana, a stunning replica of an 18th-century British Navy vessel. It’s often open for public sails or dockside tours during special events.

    Take a River Cruise

    For more time on the Chester River, book a cruise on The River Packet. This 65-foot, 1920s-style classic yacht and tour boat offers weekend brunch, dinner, sunset and casual tours April through November that leave right from the High Street Dock.

    For more waterfront dining experiences, check out Dock and Dine Kent Narrows MD.

    Attend Chestertown Festivals and Events

    Catch a show at the Garfield Center for the Arts at the Prince Theater housed in a beautifully restored 1920s theater or plan your visit around one of the many yearly events in Chestertown like the Chestertown Jazz Festival or the Sultana Downrigging Festival each fall which is the largest annual gathering of tall ships in North America combined with bluegrass music.

    During the Christmas season, come for ‘A Dickens of a Christmas’ festival weekend where you can “step back into 1840s London and experience the holiday season as Charles Dickens imagined it.” Activities include complimentary carriage rides through historic downtown, a ticketed house tour, food vendors, an artisan village and an authentic Victorian tea time. Wearing your Victorian best is highly encouraged.

    Get Cozy With Friendly Felines at the Cat Colloquium

    Cat Colloquium lounge interior with gray walls, multiple resident cats lounging on furniture including orange tabby in pink chair and white cat on ottoman, cat artwork on walls, bookshelves, TV screen showing aquarium, cat tree and toys throughout modern space
    Cat Colloquium lounge interior with gray walls, multiple resident cats lounging on furniture including orange tabby in pink chair and white cat on ottoman, cat artwork on walls, bookshelves, TV screen showing aquarium, cat tree and toys throughout modern space Meet the resident cats in the Cat Colloquium’s cozy second-floor lounge | Photo: Better Living

    Chestertown’s Cat Colloquium (215 High St #2C, Chestertown, MD 21620) run by nonprofit Kit Care Inc. is a warm, welcoming and unique spot for cat lovers. Here you can meet and snuggle up with resident cats, enjoy quiet time, or chat with their friendly volunteers.

    Walk through the alley next to Stam’s Luncheonette and follow the signs to the second floor. The space is bright, peaceful and playful, with cozy seating, and cat-friendly furniture (including a life-sized cat tree).

    It’s a true hidden gem and a unique experience if you’re an animal lover like us and can’t pass up an encounter with a furry friend. Visiting is free, but you can check out their blog and donation options to learn more and support them.

    If you’re traveling with 6 people or more, make an appointment before you go.

    Visit Lockbrier Farm for Fresh Produce and Homemade Ice Cream

    Lockbriar Farms autumn display with vintage green truck loaded with pumpkins and mums, red and white striped tent canopies in background, rows of colorful chrysanthemums in yellow, burgundy, orange and white arranged on ground, fall harvest decorations with corn stalks
    Lockbriar Farms autumn display with vintage green truck loaded with pumpkins and mums, red and white striped tent canopies in background, rows of colorful chrysanthemums in yellow, burgundy, orange and white arranged on ground, fall harvest decorations with corn stalks Lockbriar Farms bursts with fall colors and fresh seasonal produce | Photo: Better Living

    For a farm experience, an eight-minute drive from downtown Chestertown, go to Lockbrier Farm to pick berries, flowers and pumpkins, savor farm-churned ice cream, and stock up on fresh, local and seasonal produce.

    Since 1993, the Lockwood family—whose farming roots stretch back to the Civil War—has opened the gates of Lockbrier Farms (10051 Worton Rd, Chestertown, MD 21620) to visitors seeking fresh air, vibrant blooms, and the joy of picking their own seasonal produce.

    During our recent fall visit, they were brimming with mums, pumpkins, Indian corn and gourds in every color. Seasonally, you can pick your own fruits like strawberries, blueberries, raspberries, and blackberries. Wander through their flower and herb gardens, where you can cut your own to create your own DIY bouquet.

    Then shop the farm stand and stock up on fresh produce, apple cider, jams, pickled veggies, local honey, and treats like apple butter, eggs and fresh cheese.

    After exploring the farm, head over to their ice cream barn for a scoop of their incredible homemade ice cream in 28+ rotating flavors like strawberry and lemon cookie. It’s made on-site with Lockbrier’s own grown and locally sourced ingredients and is some of the best in Kent County.

    Lockbrier Farm is open daily (weather permitting), May through Thanksgiving, and there’s no admission fee. Wear boots you won’t mind getting dirty if you plan to explore the fields.

    Where to Shop in Chestertown MD

    Fall street scene in historic Chestertown Maryland showing The Bookplate independent bookstore with red and cream striped awning, brick sidewalk with pumpkins and hay bale decorations, Book Plate hanging sign, neighboring shops including Twigs and Teacups, autumn tree with orange leaves, chalkboard sign with black cat
    Fall street scene in historic Chestertown Maryland showing The Bookplate independent bookstore with red and cream striped awning, brick sidewalk with pumpkins and hay bale decorations, Book Plate hanging sign, neighboring shops including Twigs and Teacups, autumn tree with orange leaves, chalkboard sign with black cat Downtown Chestertown’s brick-lined streets come alive with fall charm | Photo: Better Living

    If you’re bored with cookie-cutter tourist traps, you’ll love Chestertown’s authentically independent spirit. It has 200 locally owned shops, galleries, restaurants, bakeries, and cafes where you can take your time browsing handmade goods, rare books and discovering one-of-a-kind finds.

    Twigs & Teacups

    Twigs and Teacups gift shop interior display showing eclectic home goods including woven basket, black poodle figurines in wooden bowl, gold dome lamp, flatware set, think like a chef cookbook, decorative candles, orange placemats, patterned mugs, colorful linens and kitchen accessories arranged on counter with bookshelves visible in background
    Twigs and Teacups gift shop interior display showing eclectic home goods including woven basket, black poodle figurines in wooden bowl, gold dome lamp, flatware set, think like a chef cookbook, decorative candles, orange placemats, patterned mugs, colorful linens and kitchen accessories arranged on counter with bookshelves visible in background Twigs & Teacups overflows with whimsical gifts and unique home goods | Photo: Better Living

    If you only have time to go into one store in Chestertown, make it Twigs & Teacups (111 S Cross St, Chestertown, MD 21620). Everyone we asked for local recommendations said it was their favorite store.

    Way bigger than it looks from the outside, this 2-story shop is filled with a curated collection of whimsical and unique gifts packed with personality, including everything from quirky kitchenware and nostalgic toys to locally made goods, stationery, books, puzzles, clothing and seasonal treasures. Give yourself plenty of time to browse, because there’s so much to see.

    Pricing is affordable, and the friendly staff, which includes their resident cat Jonathan, will help you find a unique gift for any occasion.

    Chester River Wine & Cheese Co.

    Interior of Chester River Wine & Cheese Co showing wire shelving filled with gourmet products including colorful pasta packages and specialty items on a turquoise shelf unit. In the foreground, a black wire rack displays multiple glass bottles of infused olive oils with pour spouts for sampling, alongside rows of small jars containing flavored honey in golden and amber hues. Additional shelves in the background hold various gourmet food products. Warm yellow walls and natural light from windows create an inviting atmosphere
    Interior of Chester River Wine & Cheese Co showing wire shelving filled with gourmet products including colorful pasta packages and specialty items on a turquoise shelf unit. In the foreground, a black wire rack displays multiple glass bottles of infused olive oils with pour spouts for sampling, alongside rows of small jars containing flavored honey in golden and amber hues. Additional shelves in the background hold various gourmet food products. Warm yellow walls and natural light from windows create an inviting atmosphere Sampling the incredible selection of infused olive oils and artisan foods at Chester River Wine & Cheese Co.

    A few doors down, foodies and wine lovers must pop into Chester River Wine & Cheese Co. (117 S Cross St, Chestertown, MD 21620) This cozy gourmet shop and local favorite offers a curated selection of wines from around the world, and cut-to-order cheeses, charcuterie, olives, pickles, jam, snacks and specialty items. Build a picnic to take to the riverfront or gather snacks for winding down later.

    The staff here are happy to offer pairings or samples, and the shop often hosts tastings and seasonal events. Whether you want a new wine to try or you’re a fromage fanatic, this shop is a delicious detour.

    The Bookplate

    Interior of The Bookplate independent bookstore in Chestertown Maryland showing white bookshelves filled with children's books including The Three Pigs, Ghostly Terrors, and Halloween books, with a large white decorative rabbit statue, whimsical wall mural with stars and houses in background
    Interior of The Bookplate independent bookstore in Chestertown Maryland showing white bookshelves filled with children's books including The Three Pigs, Ghostly Terrors, and Halloween books, with a large white decorative rabbit statue, whimsical wall mural with stars and houses in background The Bookplate’s charming children’s section features whimsical finds and rare titles | Photo: Better Living

    Book lovers should head across the street, where they can get lost in the shelves at The Bookplate (112 S Cross St, Chestertown, MD 21620).

    This independent used bookstore, which also sells vintage prints and pottery, has an enormous selection with a wide variety of genres and hard to find titles. The selection here is truly one of a kind, and the books are well organized. If there’s something you want but don’t see, ask the staff, and they may have it hidden in the stacks or can special order it.

    Where to Eat in Chestertown MD

    With so much to do here, there’s no doubt you’ll get hungry. When you want to eat, Chestertown has a delicious mix of options, from Chesapeake seafood, farm-to-table fare, international flavors, casual eats and cozy comfort food.

    Stam’s Luncheonette

    Stam's Luncheonette exterior showing historic white two-story building with black shutters, curved bay windows on first floor, red door entrance, bright yellow metal bistro tables and chairs on brick plaza, ice cream cone sign, blue sky
    Stam's Luncheonette exterior showing historic white two-story building with black shutters, curved bay windows on first floor, red door entrance, bright yellow metal bistro tables and chairs on brick plaza, ice cream cone sign, blue sky Stam’s Luncheonette serves nostalgic comfort food in a restored historic soda fountain | Photo: Better Living

    For a casual bite, Stam’s Luncheonette (215 High Street, Chestertown, MD 21620) is a retro-style lunch counter, soda fountain and ice cream shop in a restored space that was originally Chester Pharmacy, opened by a local named John Stam about 175 years ago.

    The mantra here is nostalgic charm serving up casual and classic American lunch staples like Pizza Grilled Cheese, Dill Chicken Salad sandwiches and tomato soup. Our favorite is their famous signature juicy Butter Burger served with cheddar cheese, caramelized onions, and on a buttery toasted brioche bun. It’s oh so buttery and worth every darn calorie.

    A local favorite is their in-house made ice cream and sundaes made with creative rotating seasonal flavors like Oatmilk Chai and Honeycomb + Graham Cracker. They even have pints of ice cream to go. It’s a must-stop if you’re craving cozy comfort food with flavors that never go out of style.

    The Kitchen at the Imperial

    lose-up of a golden-brown jumbo lump crab cake with crispy edges on a white plate, accompanied by a side of sautéed zucchini and corn succotash. A ramekin of orange remoulade sauce and what appears to be coleslaw are visible in the background. A silver fork rests on the right side of the plate. The crab cake shows large chunks of premium crab meat with minimal filler and a perfectly seared crust.
    lose-up of a golden-brown jumbo lump crab cake with crispy edges on a white plate, accompanied by a side of sautéed zucchini and corn succotash. A ramekin of orange remoulade sauce and what appears to be coleslaw are visible in the background. A silver fork rests on the right side of the plate. The crab cake shows large chunks of premium crab meat with minimal filler and a perfectly seared crust. The award winning crab cake at The Kitchen at Imperial – a must-try when visiting Maryland’s Eastern Shore. | Photo: Better Living

    After 25 years in the tech world, Chef Steve Quigg traded IT consulting for culinary creativity, and is the heart behind The Kitchen at the Imperial (208 High Street, Chestertown, MD 21620). It’s one of Chestertown’s most beloved casual upscale dining spots, where every dish feels like a celebration of the Eastern Shore.

    Winner of Best Chef on the Eastern Shore three years in a row, Chef Steve crafts his farm-to-table menu inspired by what’s harvested fresh from both the local farms and waterways. The menu changes here often, and everything from the dinner rolls and hand-cut fries and desserts is made in-house.

    A must-try here is the Braised Lamb Shank and the signature crab cakes with absolutely no filler, packed with fresh lump crabmeat, perfectly seasoned and paired with local produce and house-made sauces for an elevated twist. They’ve won multiple awards for ‘Best Crab Cake’, including honors from What’s Up? Magazine and Chesapeake Bay Magazine. Pair it with their Rosemary Grapefruit Margarita or a glass of wine from their extensive curated international wine list.

    Open for lunch, dinner and brunch on Sundays, The Kitchen at the Imperial is closed Tuesdays.

    Retriever Bar

    Retriever Bar house burger on golden brioche bun with juicy grass-fed beef patty, melted white cheese, shredded lettuce, pickles and bistro sauce, served with crispy hand-cut fries on white plate
    Retriever Bar house burger on golden brioche bun with juicy grass-fed beef patty, melted white cheese, shredded lettuce, pickles and bistro sauce, served with crispy hand-cut fries on white plate The Retriever Bar’s House Burger features locally raised grass-fed beef | Photo: Better Living

    The 21 and over Retriever Bar (337 1/2 High Street, Chestertown, MD 21620) blends Chesapeake flavor with a modern lounge feel and craft cocktails. Cozy up in the lounge, grab a seat at the bar, which boasts one of the most extensive spirit selections in town, including rare bourbons and whiskeys.

    It’s also Chestertown’s go-to spot for raw, locally sourced Chesapeake Bay oysters, small plates like Ceviche, Warm Goat Cheese and Pickled Beets and mains like Shrimp and Grits and Lamb Birria Tacos. Whether you’re sipping something bold or nibbling on a cheese board, everything is thoughtfully crafted here.

    We love the House Burger – a juicy double smash burger with locally raised, grass-fed St. Brigid’s beef, American cheese, pickles, shredded lettuce slathered with bistro sauce served on a toasted brioche roll served with fries on the side.

    For dessert, try their delicious Apple Strudel with a scoop of creamy vanilla ice cream from Stam’s Luncheonette.

    El Rancho Mexican Cuisine

    Three authentic Mexican street tacos on warm corn tortillas with seasoned meat, diced onions and fresh cilantro on red and white checkered paper, served with cucumber slices, radish, lime wedges and small bowl of salsa verde on wooden board
    Three authentic Mexican street tacos on warm corn tortillas with seasoned meat, diced onions and fresh cilantro on red and white checkered paper, served with cucumber slices, radish, lime wedges and small bowl of salsa verde on wooden board El Rancho serves authentic Mexican street tacos with hand-pressed tortillas | Photo: Better Living

    For authentic Mexican flavors, El Rancho Mexican Cuisine (851 Washington Ave, Chestertown, MD 21620) is a few minutes outside downtown. Opening early (6:30 AM most days) it’s one of the few places in town where you can grab a full hot breakfast. The authentic Mexican menu offers everything from omelets and pancakes to quesadillas, burritos, fajitas, and bowls and platters.

    We love the tender steak and flavorful Al Pastor Mexican Street Tacos here, which are served in warm, hand-pressed tortillas. We also ordered the chicken enchiladas, ½ red and ½ green, served with black beans. They were delicious, satisfying and really packed some heat.

    See also

    Split image showing luxury car transport services - left side features a red Lamborghini with scissor doors open in an upscale garage setting, right side shows a red SUV loaded on a multi-level car carrier trailerSplit image showing luxury car transport services - left side features a red Lamborghini with scissor doors open in an upscale garage setting, right side shows a red SUV loaded on a multi-level car carrier trailer

    El Rancho is casual, affordable, and perfect for travelers craving bold flavors in a laid-back setting. Our server, Jordan, was super friendly, and we’re excited to try the spicy watermelon margarita next visit. El Rancho is open 7 days a week for breakfast, lunch and dinner.

    Modern Stone Age Kitchen

    Behind-the-scenes view of Modern Stoneage Kitchen bakery showing professional bakers working at a large wooden table preparing dough. Wire shelving racks in the foreground display dozens of freshly baked artisan bread loaves with golden-brown crusts dusted with flour. A brick oven is visible in the background along with stainless steel commercial baking equipment. The industrial kitchen features polished concrete floors and bright overhead lighting.
    Behind-the-scenes view of Modern Stoneage Kitchen bakery showing professional bakers working at a large wooden table preparing dough. Wire shelving racks in the foreground display dozens of freshly baked artisan bread loaves with golden-brown crusts dusted with flour. A brick oven is visible in the background along with stainless steel commercial baking equipment. The industrial kitchen features polished concrete floors and bright overhead lighting. Fresh artisan bread cooling at Modern Stoneage Kitchen in downtown Chestertown.

    Modern Stone Age Kitchen (236 Cannon St, Chestertown, MD 21620) founded by food anthropologist and former Washington College professor Dr. Bill Schindler and author of “Eat Like a Human: Nourishing Foods and Ancient Ways of Cooking to Revolutionize Your Health,” this bakery, cafe and espresso bar open for breakfast and lunch is a one-of-a-kind edible destination.

    Here you can buy sourdough breads, bagels, croissants, pastries and scratch-made meals for breakfast and lunch prepared according to ancestral food traditions made with ingredients like organic flour and lard and cooking techniques like fermentation that create the most nutrient-dense foods.

    Our favorite is their delicious hand-rolled sourdough pretzels, which sell out fast. You can also grab refrigerated prepared foods to go like fermented veggies, yogurt, cheeses and house-made liverwurst.

    Bakery seating is available inside, but it fills up quickly. When it’s warm, head to their pretty courtyard outside. If you’re interested, check their calendar of classes to learn ancient food prep skills like sourdough baking and fermentation.

    Where to Stay in Chestertown MD

    Brampton 1860 historic brick inn at dusk with starry night sky, showing three-story red brick building with white wraparound porch, glowing windows, decorative fountain in manicured garden with colorful flowers, trees on either side
    Brampton 1860 historic brick inn at dusk with starry night sky, showing three-story red brick building with white wraparound porch, glowing windows, decorative fountain in manicured garden with colorful flowers, trees on either side Brampton 1860’s stunning 19th-century architecture glows against a starlit Eastern Shore sky | Photo: Better Living

    Brampton 1860

    Stay longer and wake up at a luxurious historic 19th-century boutique inn on a lush private 35-acre estate, 1 mile from downtown Chestertown at Brampton 1860.

    A TripAdvisor Traveler’s Choice Winner, featured on The Viewpoint with Dennis Quaid listed on the Select Registry, Brampton 1860’s (25227 Chestertown Road Chestertown, MD 21620) perfectly restored historic architecture, tranquil atmosphere, authentic hospitality and attention to detail have earned it top ratings and a loyal following.

    Inside Marleys Cottage at Brampton 1860 with king bed, cozy furnishings, red accent wall, fireplace, and French doors opening to a private patio
    Inside Marleys Cottage at Brampton 1860 with king bed, cozy furnishings, red accent wall, fireplace, and French doors opening to a private patio Inside Marley’s Cottage at Brampton 1860 | Photo: Better Living

    Wake up in one of the seven thoughtfully appointed rooms and suites in the main house or six private cottages scattered throughout the property. Each has luxurious amenities like spa tubs, fireplaces, luxurious Comphy™ linens, smart TVs and free Wi-Fi.

    Each morning, enjoy a freshly prepared multi-course gourmet à la carte breakfast in their sunlit dining room with menu options like Lemon Croissant French Toast and Apple Pancakes that change daily. Have it served on their sprawling porch, deck or breakfast room. Seasonal ingredients, homemade pastries, and warm hospitality are always included.

    Stack of three golden buttermilk pancakes dusted with powdered sugar on white plate with blue rim, garnished with fresh strawberries and blackberries, served with crispy bacon strips and small bowl of maple syrup on white linen placematCaption:
    Stack of three golden buttermilk pancakes dusted with powdered sugar on white plate with blue rim, garnished with fresh strawberries and blackberries, served with crispy bacon strips and small bowl of maple syrup on white linen placematCaption: Brampton 1860’s gourmet à la carte breakfast features daily specials like fluffy pancakes | Photo: Better Living

    Throughout the day, help yourself to a selection of baked goods and then return in the afternoon for their Afternoon Tea for delicious small plates, dessert, complimentary wine, coffee and tea. After breakfast, visit their flock of chickens and then walk through Brampton’s formal gardens with fruit trees, trails and wild meadows that attract birds, butterflies, and small wildlife.

    At night, curl up with a book by the fireplace, do a puzzle in the library or enjoy a glass of wine in their bar and lounge. We love relaxing by the outdoor firepit where we can see tons of stars. Don’t be surprised if their cat Squeaky comes by to keep you company.

    Cozy library room at Brampton 1860 with floor-to-ceiling white built-in bookshelves, brown leather sofa with rust-colored pillows, arched fireplace with white mantel decorated with fall pumpkins and dried flowers, oriental rug, table lamps, and large window with yellow curtains
    Cozy library room at Brampton 1860 with floor-to-ceiling white built-in bookshelves, brown leather sofa with rust-colored pillows, arched fireplace with white mantel decorated with fall pumpkins and dried flowers, oriental rug, table lamps, and large window with yellow curtains Curl up with a book in Brampton 1860’s inviting library by the fireplace | Photo: Better Living

    With personalized service, Brampton 1860 offers a unique experience that feels both timeless and welcoming. And you’ll have the best of both worlds: accommodations at a peaceful, luxurious, historic countryside estate and the convenience of Chestertown’s indie shops, galleries, and restaurants just 5 minutes away. Brampton is adults-only and pet-friendly. EV charging stations are available. For the best rates, book direct.

    💡 Read our complete Brampton 1860 Review and discover Fall Fun at Brampton 1860 for seasonal activities.

    Getting to Chestertown, MD

    On Maryland’s Eastern Shore in Kent County, Chestertown is:

    • 1 hour from Wilmington, DE
    • 1.5 hours from Baltimore
    • 1.5 hours from Washington, D.C.
    • 1.5 hours from Philadelphia

    Driving: If you’re driving, you can reach Chestertown via Route 213 or Route 301, whether you’re coming from the north or south.
    Flying: The nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), about 70 miles away. From BWI, you can rent a car or take a shuttle service to Chestertown.
    Boating: Dock at the Chestertown Marina. Check slip rates here and call 410-778-3616 to book your transient slip.
    Parking: Once in Chestertown, parking is free and convenient. Options include on-street parking on High Street, Cross Street, and Queen Street, as well as multiple free municipal lots with time limits on Spring Street, Cannon Street, and Calvert Street.
    Chestertown makes the perfect addition to any Maryland Eastern Shore itinerary. Consider it as part of your day trips from Washington DC or explore more with the best day trips from Philadelphia for nature lovers.

    Final Thoughts

    Chestertown, Maryland, is a historic Eastern Shore town known for its brick-lined streets, colonial architecture, and scenic riverfront.

    Founded in the 1700s, it offers a charming escape with over 200 independent shops, galleries, and cafes, with a variety of things to do and events.

    It makes the perfect getaway or day trip if you want to discover a unique destination with tons of charm and without the crowds.

    For a peaceful and luxurious retreat a few minutes from downtown Chestertown, stay at Brampton 1860.

    Chestertown is compact but full of things to do!

    Whether you’re planning a romantic weekend, a solo escape, or a family-friendly adventure, Chestertown offers something for everyone:

    • History lovers can explore colonial architecture and heritage sites
    • Foodies can enjoy farm-to-table dining and homemade ice cream
    • Browse indie boutiques for unique finds
    • Explore the historic waterfront or take a river cruise
    • Pick your own berries at Lockbriar Farms, then cool off with homemade ice cream
    • Support local and shop Chestertown Farmers’ Market (Saturdays, March–December) for fresh produce, flowers, and handmade goods

    For more charming Eastern Shore destinations, explore Onancock, Virginia, Cape Charles, Virginia, The Oaks Waterfront Hotel, and Chincoteague.

    Better Living uses affiliate links. If you make a purchase through them, we may receive a small commission (for which we are deeply grateful) at no cost to you.

    Heather

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  • Food, Wine, and Fall Fun at Brampton 1860 – Chestertown, MD | Better Living

    Looking for the best Halloween getaway in Maryland? This Eastern Shore bed and breakfast becomes a spooky wonderland each October, offering wine dinners, adult trick-or-treating, and luxury accommodations just 2 hours from DC. Here’s our complete guide to Brampton 1860’s fall festivities and why it’s Maryland’s top-rated romantic inn for autumn escapes.

    BRAMPTON 1860 AT A GLANCE

    • Location: 25227 Chestertown Road, Chestertown, MD
      ▸ Eastern Shore setting, 2 hours from Baltimore or DC, 1 hour from Wilmington
    • Vibe: Romantic boutique luxury on a historic 35-acre estate
    • Price Range: $$–$$$ (Typically $229–$450 depending on room and season)
    • Accommodations: Manor House rooms and private cottages with fireplaces, jetted tubs, and Japanese soaking tubs
    • Dining: Farm-to-table breakfast, afternoon tea, seasonal dinners, and local restaurant partnerships
    • On-Site Perks: Walking trails, gardens, fire pit, Certified Wildlife Habitat, EV charging, and resident chickens
    • Awards & Recognition:
      • Select Registry member since 2001
      • Listed on the National Register of Historic Places
      • Certified Wildlife Habitat designation
    • Best For: Romantic getaways, anniversaries, fall retreats, history lovers, nature-focused escapes
    • Reservations: BramptonInn.com  or (410) 778-1860

    Halloween Fun at Brampton 1860

    “I haven’t had this much fun at Halloween since I was a kid.”

    The woman at the next table wasn’t exaggerating. Some historic inns give you tasteful fall decorations and call it a season. Brampton 1860 in Chestertown, MD gives you a head groundskeeper dressed as a T-Rex handing out candy, a violinist playing while skeletons lounge by a charcuterie, and a five-course wine dinner where the second course comes with a plastic spider on top. Oh, and adult trick-or-treating through a candlelit 35-acre estate at night.

    This is not your grandmother’s bed and breakfast.

    Over three October days, we watched this 1860s Eastern Shore manor transform for fall and Halloween. Not with a few pumpkins and some mums, but with the kind of all-in seasonal commitment that makes you wonder why every place doesn’t try this hard.

    Around us, adults in their 50s, 60s, and 70s were giggling over googly-eyed salads, posing with dinosaurs, and comparing their trick-or-treat candy hauls like competitive children. We were sipping curated wine. Eating chef-crafted Southern cuisine. And yes, also sneaking extra chocolate from the monster-guarded candy bar.

    Welcome to fall at Brampton 1860, where a 19th-century manor on Maryland’s Eastern Shore has figured out something most places miss: sophisticated doesn’t have to mean serious.

    The Grape Expectations Halloween Dinner was the centerpiece, sure. But autumn magic was everywhere.

    Arriving in Autumn: Historic Chestertown Sets the Scene

    Book Plate bookstore with red awning and storefront window, scarecrow decorations, pumpkins stacked by entrance, blue Cat Colloquium sandwich board sign, brick sidewalk with other shops visible including blue awning Charming shops line Chestertown’s brick sidewalks | Photo: Better Living

    We started our weekend in Historic Chestertown, MD –  just a four minute drive from the Brampton Inn. The colonial river town had fully committed to fall, with Halloween decorations adorning every storefront and charming scarecrows lining the brick sidewalks throughout downtown.

    Chester River waterfront view with tall ship and sailboats docked at marina, brick walkway with park bench in foreground, green leaves framing top of image, fall foliage visible across river, blue sky with puffy clouds
    Chester River waterfront view with tall ship and sailboats docked at marina, brick walkway with park bench in foreground, green leaves framing top of image, fall foliage visible across river, blue sky with puffy clouds Historic Chestertown’s waterfront on the Chester River | Photo: Better Living

    The waterfront along the Chester River offered peaceful walking paths where early fall colors were just beginning to show. While late October hadn’t yet brought peak foliage, the hints of what November would deliver were everywhere. The town’s authentic charm, free from tourist trap syndrome, made it clear why people keep returning to this corner of the Eastern Shore.

    We strolled the quaint shops and historic streets, soaking in the small-town atmosphere before heading to Brampton 1860 for check-in.

    Returning to Marley’s Cottage

    Brampton 1860 blue and gold entrance sign decorated with dried corn stalks, surrounded by chrysanthemums, pumpkins, and ornamental grasses on stone wall
    Brampton 1860 blue and gold entrance sign decorated with dried corn stalks, surrounded by chrysanthemums, pumpkins, and ornamental grasses on stone wall Fall welcomes you from the moment you arrive | Photo: Better Living

    Pulling into Brampton 1860 felt like coming home. The inn’s entrance, decorated with corn stalks, mums, and pumpkins, immediately signaled the seasonal shift. But the real magic awaited at Marley’s Cottage, where that famous red door once again delivered its surreal reveal. What looks like an old barn from the parking area opens to expose a bright, spacious 1,000-square-foot retreat that remains completely hidden from view until you step through.

    Bright, airy cottage bedroom with vaulted ceiling, king bed with white linens and burgundy leather bench at foot, two burgundy leather recliners, sliding barn door to bathroom, red accent lamps, colorful area rug, hardwood floors
    Bright, airy cottage bedroom with vaulted ceiling, king bed with white linens and burgundy leather bench at foot, two burgundy leather recliners, sliding barn door to bathroom, red accent lamps, colorful area rug, hardwood floors Inside Marley’s Cottage at Brampton 1860 | Photo: Better Living

    Having stayed here during summer, we knew what to expect, yet the cottage’s appeal only grew stronger. The screened porch with its Japanese soaking tub now overlooked autumn meadows. The wood-burning fireplace was primed for cozy evenings. Even the front porch swing, our morning coffee spot, felt more inviting with fall’s crisp air replacing the warm summer mornings.

    The Manor House at Brampton 1860

    Brampton 1860's three-story red brick Georgian manor house with white columned porch surrounded by vibrant orange and yellow fall foliage under blue sky with puffy clouds
    Brampton 1860's three-story red brick Georgian manor house with white columned porch surrounded by vibrant orange and yellow fall foliage under blue sky with puffy clouds Fall colors frame the Manor House at Brampton 1860 | Photo: Better Living

    After settling in, we walked the two minutes to the Manor House for coffee and cookies, a ritual that never gets old. Seeing Innkeepers Hilari and Dave again was wonderful. Their genuine enthusiasm for Brampton and their guests creates an atmosphere where returning visitors feel like old friends rather than repeat customers.

    Cozy library with floor-to-ceiling built-in bookshelves, brown leather furniture, fireplace with fall decorations on mantel, warm yellow walls and oriental rug
    Cozy library with floor-to-ceiling built-in bookshelves, brown leather furniture, fireplace with fall decorations on mantel, warm yellow walls and oriental rug The Manor House library dressed for autumn | Photo: Better Living

    Over coffee, they shared details about the evening’s Halloween dinner and what to expect. The planning, they explained, had been extensive. Head Groundskeeper Geoff had been carving dozens of pumpkins and decorating the property all week. The kitchen team had perfected their playful Southern Gothic menu. Monica from DMV Distributing had selected wines specifically to complement both the food and the spooky theme. Every detail had been considered.

    Chocolate chip muffins decorated with white frosting ghosts with chocolate chip eyes and mouths, arranged on silver serving tray with pumpkin in background
    Chocolate chip muffins decorated with white frosting ghosts with chocolate chip eyes and mouths, arranged on silver serving tray with pumpkin in background Afternoon tea gets the Halloween treatment | Photo: Better Living

    The afternoon teatime that day highlighted seasonal treats that bridged the gap between Brampton’s daily hospitality and the dining event ahead. Ghostly muffins, pumpkin shaped deviled eggs, fresh baked cookies, and the warm welcome from staff who remembered us from months earlier reinforced why we love it here.

    Dinner in Chestertown: The Retriever Bar

    hick burger with melted cheese on brioche bun with lettuce and special sauce, served with generous portion of golden french fries on white plate, restaurant setting
    hick burger with melted cheese on brioche bun with lettuce and special sauce, served with generous portion of golden french fries on white plate, restaurant setting The Retriever Bar’s perfectly cooked House Burger | Photo: Better Living

    That first evening, we headed back to Chestertown for dinner at The Retriever Bar. The restaurant has a great vibe with a nice bar up front and dining area in the back. The House Burger was cooked to perfection and generously portioned with crispy fries. We also tried the shrimp and grits, which arrived beautifully presented with stone-ground grits. Our server Kassie was fantastic, providing friendly service and local recommendations.

    Kassie mentioned something unexpected: The Cat Colloquium, located right above Stam’s Luncheonette.

    The Cat Colloquium

    Siamese cat with dark face and cream body receiving head scratches from visitor's hand, cat's eyes contentedly closed, sitting on lap covered with cat-patterned blanket in indoor cat cafe setting
    Siamese cat with dark face and cream body receiving head scratches from visitor's hand, cat's eyes contentedly closed, sitting on lap covered with cat-patterned blanket in indoor cat cafe setting Making friends at The Cat Colloquium | Photo: Better Living

    This warm, friendly space invites visitors to relax and play with 13 resident cats, free of charge. Donations are appreciated but not necessary, and the inquisitive felines make it a surprisingly calming experience. The Cat Colloquium is exactly the kind of quirky, genuine attraction that makes small town exploration so rewarding.

    Morning Transformation: Halloween Takes Over

    Stack of fluffy pancakes with maple syrup, crispy bacon, scrambled eggs, fresh berries including strawberries and blackberries on white plate with decorative quilt placemat
    Stack of fluffy pancakes with maple syrup, crispy bacon, scrambled eggs, fresh berries including strawberries and blackberries on white plate with decorative quilt placemat Fall inspired Apple Pancakes with local bacon and fresh eggs at Brampton | Photo: Better Living

    Breakfast is included at Brampton, and always a highlight. The menu changes daily, featuring fresh, locally sourced ingredients, including eggs from the inn’s own chickens. The coffee stays hot, and watching the Manor House kitchen in action, you can feel the care going into every plate.

    That morning, though, felt extra special as Halloween came alive in real time. Geoff and the staff were everywhere, turning Brampton into a spooky wonderland. Skeletons appeared on the porch, spider webs draped the trees, jack-o-lanterns lined the pathways, and a full-size witch on a vintage bicycle greeted us on the walk back to our cottage. The decorations struck a fun balance between sophisticated and playfully ghoulish.

    Life-size witch figure with green face and black robes positioned on vintage bicycle on lawn with fall trees in background
    Life-size witch figure with green face and black robes positioned on vintage bicycle on lawn with fall trees in background The witch on wheels that greeted cottage guests | Photo: Better Living

    We spent much of the morning exploring the 35 acres as the setup continued. The trails here are well-maintained and easy to navigate with multiple spots to pause and take in the natural beauty. Even in late October, before peak foliage, we were surrounded by seasonal color.

    A Picnic Worth Staying In For

    Bowl of rich beef stew with chunks of meat, carrots, potatoes and peas in thick gravy, served with side salad and red wine on woven placemat
    Bowl of rich beef stew with chunks of meat, carrots, potatoes and peas in thick gravy, served with side salad and red wine on woven placemat The perfect fall meal: Brampton’s hearty beef stew picnic | Photo: Better Living

    Rather than venture out for lunch, we’d arranged for Brampton’s beef stew picnic to be delivered to our cottage. This turned out to be another one of the trip’s highlights.

    The meal arrives in a large basket that you can take anywhere. It’s a hearty portion of stew for two with plenty of tender meat in a rich, flavorful base. Fresh bread and butter accompanied it, along with salad, a bottle of wine, and two brownies for dessert. The portions were generous enough that we could have easily stretched it further.

    What made it particularly appealing was not needing to leave the property when we simply wanted to unwind. Brampton’s onsite dining options, with menus that change seasonally, provide real convenience without sacrificing quality. While dining in Chestertown is wonderful, not much compares to enjoying a chef-prepared meal on your private cottage porch, surrounded by fall foliage, with nothing on the agenda except relaxation.

    Grape Expectations: 5 Course Halloween Wine Dinner

    Brampton 1860 manor house at sunset with dramatic pink and orange sky, fountain in foreground, manicured lawn and historic architecture highlighted by warm evening light
    Brampton 1860 manor house at sunset with dramatic pink and orange sky, fountain in foreground, manicured lawn and historic architecture highlighted by warm evening light Brampton 1860 decorated for Halloween at sunset | Photo: Better Living

    As evening approached, anticipation built. Guests began gathering, many in subtle Halloween touches that added to the festive atmosphere without anyone taking it too seriously. The Manor House and surrounding grounds had turned into something spectacular.

    A Monster Welcome

    Close-up of furry brown monster glove with tiger-striped claws holding champagne flute against green ivy wall, showing the playful Halloween spirit
    Close-up of furry brown monster glove with tiger-striped claws holding champagne flute against green ivy wall, showing the playful Halloween spirit A monster hand offers guests a welcome glass of sparkling wine | Photo: Better Living

    Our first hint that this wasn’t going to be a typical wine dinner came right away. As we walked past the garden wall, a furry monster hand reached out through an opening and offered us glasses of sparkling wine. The whimsical touch set expectations perfectly. This would be sophisticated, playful, and delightfully spooky.

    The outdoor dining setup under the string lights looked even better as the sun went down. Tables near the fire pit created just enough coziness without feeling crowded. The decorations we’d seen being put up earlier now glowed in the evening light, and violinist Janice Mahan played throughout dinner, adding a calm, refined layer to the Halloween fun.

    Grape Expectations Halloween Wine Dinner Menu

    Outdoor patio dining scene with guests at tables, orange skeleton decoration visible at buffet table, string lights overhead, black cat walking through scene
    Outdoor patio dining scene with guests at tables, orange skeleton decoration visible at buffet table, string lights overhead, black cat walking through scene Brampton guests enjoying dinner as Squeaky wanders by | Photo: Better Living

    Monica Connors from DMV Distributing walked us through each wine pairing with knowledge and warmth, making it feel less like a lesson and more like sharing something she genuinely loved.

    We started with a bewitched Southern charcuterie board. Specialty cheeses, smoky meats, and pickles celebrated the flavors of the Eastern Shore. The Prosecco from Italy was lively and refreshing, an easy way to settle in.

    The first course was a black-eyed pea salad with a cat-shaped tortilla chip perched on top, complete with googly eyes. Spain’s Jinello Dry White cut through the salad’s bold flavors and kept everything tasting bright.

    Halloween-themed bean salads in white square dishes with green cat-shaped tortilla chips and googly eyes as garnish, plastic skeleton decoration, gold spoon on black tablecloth
    Halloween-themed bean salads in white square dishes with green cat-shaped tortilla chips and googly eyes as garnish, plastic skeleton decoration, gold spoon on black tablecloth Creative plates for the Grape Expectations Halloween Wine Dinner | Photo: Better Living

    Next came lobster shrimp cakes, golden and crisp outside, tender inside, with lemon aioli and a fun plastic spider tucked on top. The Viognier Lodi from California matched the sweetness of the seafood without getting in the way.

    The jambalaya was a masterclass in Southern cooking. Shrimp, crab, and smoky sausage swam in a rich, spicy sauce over ghost cornbread that soaked up every drop. California Zinfandel held its own against the heat and the bold flavors.

    Elegant fireplace mantel decorated with skeleton figures, black candles, paper bats on walls, bourbon cocktail with bone stirrer held in foreground, pumpkin on floor
    Elegant fireplace mantel decorated with skeleton figures, black candles, paper bats on walls, bourbon cocktail with bone stirrer held in foreground, pumpkin on floor Sipping a Wa Barrel Bomb bourbon cocktail with a bone swizzle in the lounge | Photo: Better Living

    For dessert, The Lane Cake was stacked with bourbon-soaked raisins, coconut, and pecans under a fluffy layer of frosting, topped with cherries and googly eyes. It came with a Wa Barrel Bomb bourbon cocktail and a bone swizzle for stirring. Sweet, boozy, and delightfully weird, it had the table laughing while the evening’s festivities were just getting started.

    Adult Trick or Treat: The Evening Continues

    Inflatable T-Rex costume and person in pink bunny onesie with scary face standing on porch with orange candy bucket and caution tape decoration
    Inflatable T-Rex costume and person in pink bunny onesie with scary face standing on porch with orange candy bucket and caution tape decoration T-Rex and nightmare bunny ready for adult trick-or-treaters | Photo: Better Living

    After dinner, the fun continued with adult trick-or-treat stations throughout Brampton. A nightmarish bunny manned one station. A T-Rex (Geoff again, deeply committed to the role) guarded another. In the ghoulishly decorated lounge, the bar overflowed with even more candy and treats.

    Elegant Manor House lounge transformed for Halloween with antique wooden bar, skeleton bartender prop, life-size witch figure in Victorian dress, crystal chandelier, gold wallpaper, fireplace decorated with black paper bats, purple LED lights, black candles on mantel, leather club chairs around small tables, oriental rug on hardwood floors
    Elegant Manor House lounge transformed for Halloween with antique wooden bar, skeleton bartender prop, life-size witch figure in Victorian dress, crystal chandelier, gold wallpaper, fireplace decorated with black paper bats, purple LED lights, black candles on mantel, leather club chairs around small tables, oriental rug on hardwood floors The ghoulishly decorated lounge where candy and spirits flowed freely | Photo: Better Living

    This extended the evening into something more than just dinner. It was a memorable experience that invited guests to explore, play, and connect. We found ourselves chatting with other couples, sharing laughs about our candy hauls, and marveling at how Brampton had made adults genuinely excited about Halloween again.

    Wide view of evening outdoor dining event with multiple round tables of guests, fire pit area visible, pergola with lights, skeleton decorations at serving station
    Wide view of evening outdoor dining event with multiple round tables of guests, fire pit area visible, pergola with lights, skeleton decorations at serving station The outdoor dining area aglow for Grape Expectations | Photo: Better Living

    Multiple guests said the same thing: this was the best Halloween celebration they’d experienced since childhood. The magic came from balancing sophistication with playfulness. Excellent wines and expertly prepared dishes sat alongside googly-eyed salads and costumed characters. The staff’s enthusiasm was also infectious. They weren’t just hosting an event. They were clearly having fun creating it, and that energy filled the entire property.

    Brampton 1860 hosts a special wine dinner each month, but they sell out quickly. Check the Brampton events page to secure your reservation early.

    Morning After: Savoring the Last Moments

    Woman in tan jacket and baseball cap standing on mowed grass trail overlooking golden meadow with fall foliage treeline displaying yellows, oranges and reds against bright blue sky with white clouds"
    Woman in tan jacket and baseball cap standing on mowed grass trail overlooking golden meadow with fall foliage treeline displaying yellows, oranges and reds against bright blue sky with white clouds" Enjoy walking trails across 35 acres with expansive views at Brampton 1860 | Photo: Better Living

    Our final morning began, as all Brampton mornings should, with coffee on the cottage swing followed by the walk to breakfast. The Manor House dining room buzzed with conversation from the previous evening. New friendships had formed over the shared experience, and the communal breakfast allowed those connections to continue.

    After eating, we took one last autumn hike along the trails. November visitors will see peak fall colors, but even in late October, the combination of changing leaves, morning light, and that cozy autumn chill made the walk memorable.

    A Final Stop in Chestertown

    Historic brick sidewalk in downtown Chestertown with red brick buildings displaying Maryland and American flags, corn stalks and spider web decorations, pumpkins and gourds on stoops, person walking, fall trees visible
    Historic brick sidewalk in downtown Chestertown with red brick buildings displaying Maryland and American flags, corn stalks and spider web decorations, pumpkins and gourds on stoops, person walking, fall trees visible Downtown Chestertown dressed for Halloween | Photo: Better Living

    Before heading home, we stopped back in Chestertown for lunch and a bit of final shopping. The town’s charm, made even more fun with Halloween decorations and sidewalk scarecrows, showed why a Brampton stay pairs so well with exploring downtown. Historic inn luxury meets small-town character, creating a getaway that feels welcoming and timeless.

    We’ll be sharing a full guide to fall in Chestertown soon, highlighting the best shops, restaurants, and seasonal activities. For now, just know that the four-minute drive from Brampton makes it easy to enjoy both the peaceful estate and the lively town.

    Why Fall at Brampton Works So Well

    Rustic red barn and tall brick silo on Brampton property with fall trees in background, showing the estate's agricultural heritage
    Rustic red barn and tall brick silo on Brampton property with fall trees in background, showing the estate's agricultural heritage Historic farm buildings add to Brampton’s 35-acre charm | Photo: Better Living

    Having now experienced both summer and fall at Brampton, it’s clear that autumn brings something truly remarkable. The crisp, comfortable temperatures make exploring the 35 acres a pleasure, and the cozy fireplaces, warm beverages, and seasonal touches create an inviting, relaxed atmosphere. The fall events calendar adds extra layers of excitement, making each stay feel unique.

    What really sets Brampton 1860 apart in autumn is the full commitment to the season. They don’t just swap out a few decorations, they rethink menus, adjust activities, and craft experiences that capture the essence of fall. The Halloween dinner was a perfect example. Not just wine and food with a spooky twist, but a celebration of the season, Southern cuisine, and the simple joy of gathering with others.

    Planning Your Fall Visit To Brampton 1860

    Outdoor evening dining event with guests seated at round tables under string lights, gravel pathway leading to illuminated brick manor house, fall trees surrounding patio area
    Outdoor evening dining event with guests seated at round tables under string lights, gravel pathway leading to illuminated brick manor house, fall trees surrounding patio area Grape Expectations Halloween Dinner under the stars | Photo: Better Living

    The best time to experience Brampton depends on what you’re seeking. Late October brings comfortable temperatures, Halloween events, and foliage beginning its transformation. Early to mid-November offers peak fall colors and perfect hiking weather. Late November features Thanksgiving celebrations and that cozy retreat atmosphere that makes extended stays so appealing.

    Marley’s Cottage remains our top recommendation for its privacy, space, and that unforgettable red door entrance. The Japanese soaking tub on the screened porch becomes especially inviting during fall evenings. Manor House rooms offer easy access to common areas, ideal for guests who want to maximize time in the library and social spaces.

    When planning, check Brampton’s event calendar first, then book your room and any dining experiences together. Special events like Grape Expectations require advance reservations and sell out quickly. Consider arriving a day early or staying a day after to fully enjoy the property without rushing.

    The Brampton Difference

    Woman in tan jacket sitting on ornate metal bench overlooking golden meadow with tall grasses, yellow-green leaves framing the top of image, mixed forest with fall colors in background under blue sky with white clouds
    Woman in tan jacket sitting on ornate metal bench overlooking golden meadow with tall grasses, yellow-green leaves framing the top of image, mixed forest with fall colors in background under blue sky with white clouds Perfect spots to pause along Brampton’s trails | Photo: Better Living

    What sets Brampton apart isn’t one thing. It’s how everything works together.

    An 1860s manor preserved with care, thirty-five acres of wildlife habitat, farm-to-table breakfasts with eggs from their own chickens, an exceptional staff, and innkeepers Dave and Hilari who are genuinely passionate about both preservation and hospitality. And yes, Squeaky the legendary 14-year-old black cat who clearly runs the show will gladly give you a tour if you have any snacks.

    It’s how they reinvent themselves with each season while maintaining core excellence that earned Select Registry membership and National Register of Historic Places designation. They can throw a Halloween party that has adults laughing like kids without losing any sophistication.

    Brampton succeeds because they understand something fundamental about hospitality – luxury isn’t just about fine things. It’s about experiences, attention, and moments you remember long after you leave.

    Your Fall Escape Awaits

    Autumn on Maryland’s Eastern Shore offers everything a seasonal getaway should provide. Natural beauty. Cozy atmosphere. Exceptional food. That sense of escape that comes from truly disconnecting. Brampton 1860 elevates all of it, creating experiences that exceed expectations while making everything feel effortless.

    Whether celebrating a special occasion, seeking a romantic escape, or simply wanting to experience one of the region’s finest historic inns at its most captivating season, fall at Brampton delivers.

    Ready to Book Your Brampton 1860 Getaway?

    Experience historic charm, private cottages, farm-to-table breakfasts, and serene Eastern Shore landscapes.

    Book Your Stay at Brampton 1860!

    Upcoming Events: Your Fall and Winter Calendar at Brampton 1860

    Brampton’s seasonal calendar runs well beyond Halloween. Each celebration is designed with the same attention to detail, creativity, and sense of fun that shaped the Grape Expectations Halloween dinner. Here’s what’s coming up next.

    Elegant Afternoon Tea

    November 23 and December 14, 2025
    2:00 PM to 3:30 PM
    $49 per person plus tax and gratuity

    A refined afternoon in the Manor House featuring curated teas and house-made treats. Gentle, quiet, and indulgent in the best way. Reserve by calling (410) 778-1860 to avoid additional platform fees.

    Grape Expectations: “Anything but Thanksgiving”

    November 17, 2025
    6:00 PM to 8:00 PM
    $65 per person plus $10 gratuity and tax

    Overnight guests enjoy 15% off Thursday night stays.

    This wine and small-plate tasting takes the richness of fall ingredients and steers it somewhere more creative than the usual turkey spread. Five small plates from the kitchen, each paired with wines selected by Monica Connors of DMV Distributing. Expect thoughtful pairings, playful touches, and a relaxed dining room atmosphere. Space is limited and early booking is encouraged.

    The Ultimate Eastern Shore Thanksgiving Getaway

    November 26 to 30, 2025
    Four-night package
    Save 15% on room rates

    This is Brampton’s signature holiday experience. It is not simply a place to stay for Thanksgiving. It is a complete four-day celebration that blends tradition, seasonal cooking, small-town charm, and time to relax. Many guests return for this week year after year.

    Wednesday

    Champagne welcome, live music from 3 PM to 6 PM, and chocolate treats from Bespoke Chocolate in Chestertown.

    Thursday: Thanksgiving Feast

    Social hour with champagne cocktails and live music, followed by a 5 PM feast in the Manor House dining room. Expect roast turkey, honey-baked ham, mashed potatoes, herb stuffing, Brussels sprouts, cranberry sauce, biscuits, cornbread with whipped butter, and homemade pies from Pastry Chef Carole. A glass of Crow Vineyard wine is included.

    Friday and Saturday

    Explore Chestertown’s historic downtown, visit the Saturday Farmers Market, and consider booking the Chester River cruise aboard a vintage 65-foot yacht (tickets sell out early). Expect an elevated teatime with cocktails by the fire and the Manor House transitioning into its Christmas décor.

    Sunday

    A final breakfast before departure.

    Throughout the stay: daily three-course breakfasts, decadent teatime treats, homemade cookies, and full access to the property’s 35 acres. Availability is extremely limited and advance planning is essential.

    Frequently Asked Questions About Fall at Brampton 1860

    When is peak fall foliage at Brampton 1860?

    Early to mid-November typically offers the most vibrant autumn colors, though late October begins showing beautiful seasonal changes.

    Do I need to book dining events separately from my room?

    Yes, special events like Grape Expectations require separate reservations and often sell out quickly. Book both your room and dining experiences together for the best availability.

    Is Brampton 1860 good for a romantic fall getaway?

    Absolutely. The cozy fireplaces, private cottages, autumn atmosphere, and intimate dining experiences make it ideal for couples.

    How far is Brampton from major cities?

    About 2 hours from Washington DC or Baltimore, and 1 hour from Wilmington, DE—an easy drive for a weekend escape.

    Are pets allowed at Brampton?

    Select cottages (Russell’s Cottage and Robin’s Nest) welcome pets. Book early as these rooms fill quickly.

    What’s included in the room rate?

    Full gourmet breakfast daily, afternoon tea service at 4 PM, access to all 35 acres of grounds, and use of common areas including the fire pit.

    Can I visit just for dinner without staying overnight?

    Some dining events are exclusively for overnight guests, while others welcome outside reservations based on availability. Contact Brampton 1860 directly for specific event policies.

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    Heather

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