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 2pmChristmas 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.
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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
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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.
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.
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
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
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.
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.
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
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
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.
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
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
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
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.
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
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.
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 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.
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
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
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
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
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
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
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.
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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
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
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
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.
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
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 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
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 & 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.
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
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 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
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
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
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
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
Fresh artisan bread cooling at Modern Stoneage Kitchen in downtown Chestertown.
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’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 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.
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.
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.
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
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.
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
“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
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.
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
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.
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
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.
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.
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
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
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
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.
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
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.
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
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
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.
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.
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
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.
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.
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
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
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
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
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
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.
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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Hotel Fauchere’s serene garden courtyard features a flowing fountain and complimentary beach cruisers for exploring Milford | Photo: Better Living
Peaceful waterfront views along the Chester River in Chestertown, MD. with maritime charm on full display | Photo: Better Living
