Whether your Halloween decorations have been up for weeks or you’ve been waiting patiently for that calendar page to turn, the time has come: Fall is here. So go ahead and start marking your calendar with all of the below dates, our picks for what we are somewhat arbitrarily defining as fall in Orlando — Oct. 1 through Nov. 11, or in other words, all the weeks between this, our Fall Guide, and the arrival of our Holiday Guide Wednesday, Nov. 12. — Pumpkin spicily yours, the OW editorial team.
???: Nosferatu
This is a sentimental pick for us, even through — as we type this — the Renaissance Theatre Co.’s immersive annual vampire extravaganza is on unexpected and unwelcome hiatus. The theater space has been shut down by the city after a surprise inspection revealed code violations, and there’s no clear timeline for reopening. And that sucks (wink wink) because Nosferatu is a dazzling, elegantly staged, carnal and campy delight year after year. For now, you can donate to the Ren directly or check out sister event V Bar as it haunts different venues around town like Plaza Live.
Saturday, Oct. 11: Leslie Jones
“Things are dark, but I want to give people a reason to laugh instead of cry,” says comedian and television star Leslie Jones. You know her from Saturday Night Live, the Ghostbusters reboot, her singular Olympics commentary, guest spots on The Daily Show, Supermarket Sweep v.2, or even her podcast “The Fckry” and now you can see her in person at the Plaza Live. Her comedy is audacious, unapologetic, topical and perfectly suited for the moment. 8 p.m., Plaza Live, 425 N. Bumby Ave., plazaliveorlando.org, $66-$178.
Oct. 11-12: Winter Park Autumn Art Festival
Celebrate local arts this fall at the 52nd Annual Winter Park Autumn Art Festival, the only juried fine art festival exclusively featuring Florida artists. Hosted by the Winter Park Chamber of Commerce, this weekender transforms Central Park into an outdoor gallery. Attendees can also enjoy live music, local entertainment, children’s activities and a welcoming festival atmosphere. Central Park, 251 S. Park Ave., Winter Park, winterpark.org, free.
Sunday, Oct. 12: Rocky Horror Picture Show 50th Anniversary
Oh Rocky, has the Dr. Phil got a shadowcast for you. To mark a half-century of the seminal, genderfluid, glammy midnight monster musical, Rocky Horror Picture Show screens at our most lavish downtown venue. Probably no rice-throwing during this one, but to make up for it, special guests from the film will be in the castle: Barry “Brad” Bostwick, along with accidental gothic style icons Nell “Columbia” Campbell and Patricia “Magenta” Quinn. VIP meet-and-greets seem essential. 7:30 p.m., Walt Disney Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave., drphillipscenter.org, $46-$300.
Tuesday, Oct. 14: We Wiggle Dolls: A DIY Puppet Cabaret (For Adults)
Brooklyn-born “DIY puppet cabaret” (go onnnnnn) We Wiggle Dolls comes to Conduit as part of a fall tour that promises to upend your notions of puppetry in the same way Miss Pussycat, Poncili Creacion and The Vourdalak did. We Wiggle Dolls push the art form forward, both technically — techniques and construction — and, obviously, thematically, as a more grown-up endeavor. Featuring on the night will be Naughty Little No Good, Puppet Parts Productions, Yellowlemonshapedrock and Chaz Lord from Drippy Eye Projections. You should enter this with no expectations. We certainly are …. 7 p.m., Conduit, 6700 Aloma Ave., Winter Park, conduitfl.com, $19.90.
Thursday, Oct. 16: Día de los Muertos & Monster Party
Downtown Art District’s spooky arts party returns with the 16th Annual Día de los Muertos and Monster Party at CityArts. The evening opens with two dynamic exhibitions: a Día de los Muertos showcase featuring traditional ofrendas and catrina dolls, and a monster-inspired gallery of spooky art by local and international artists. Outside on Pine Street, the festivities spill into a lively block party with food, drinks, entertainment and vendors. A frighteningly good time for all. 6 p.m., CityArts Orlando, 39 S. Magnolia Ave., downtownartsdistrict.com/ddlm, free.
Oct. 16-19: Swan Lake
Orlando Ballet kicks off their 2025/2026 season with a double dose of classic Tchaikovsky chestnuts. Of course The Nutcracker will dance in the winter holiday season, but starting things off this fall is the romantic Russian composer’s elegant and lovelorn Swan Lake, featuring choreography by Christopher Stowell and live scoring from the Orlando Philharmonic. Past productions of this iconic heartbreaker have never failed to impress, so expectations are high. Steinmetz Hall, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave., drphillipscenter.org, $43-$200.
Oct. 31-Nov. 2: Spooky Empire
Alongside the likes of Halloween Horror Nights, Phantasmagoria and Nosferatu, one of the ghoulish gems in Orlando’s Halloween crown has to be Spooky Empire. This horror-focused fandom fest provides hearty attendees with cosplay, vendors, panels and film screenings by the metric ton. But this year — and we really mean it this time — is all about the celebrity guests. It’s a terrifying bonanza with the likes of Elvira, Parker Posey, David “Art the Clown” Thornton, Chris Jericho, Method Man, Bill Moseley, Tom Savini, Nivek Ogre from Skinny Puppy, several Jasons, the cast of It, Frank from Hellraiser … we could go on, but go see for yourself (if you dare). Hyatt Regency Orlando, 9801 International Drive, spookyempire.com, $40-$299.
Sunday, Nov. 1: Beer Bacon & BBQ
Altamonte becomes the promised land for carnivores as the Beer Bacon & BBQ Festival sizzles. The name pretty much says it all; the focus is squarely on the array of roughly 40 craft beers ready for quaffing as well as meaty decadence of the bacon and barbecue (or both!) varieties proffered by local spots like Smoke in the City BBQ, Phat Ash Bakes, Big John’s Rockin’ BBQ, Heart and Soul Food Truck and more. There will be live music and games, but you might be too blissed out in a porky food coma-slash-nirvana. 2 p.m., Cranes Roost Park, 274 Cranes Roost Blvd., Altamonte Springs, beerbaconandbbq.com, $41.93.
Wednesday, Nov. 5: Doug Stanhope
Amid the bounty of righteous comedic anger we’ve got headed our way this fall, Doug Stanhope stands tall as perhaps the one radiating the most confrontational fury. Stanhope, like a latter-day Bill Hicks, is not afraid to alienate — or maybe provoke thought — as he rails against the fractured American way, clad in a rumpled thrift-store suit like a crooner with nothing to lose, with maybe a dash or two of Howard Beale for spice. 6 p.m., Funny Bone, 9101 International Drive, orlando.funnybone.com, $54-$84.
Saturday, Nov. 8: Jonathan Van Ness
Queer Eye star and ethereal delight Jonathan Van Ness is setting out on another leg of their “Hot & Healed” stand-up tour, on the fashionable heels of the release of their debut comedy special, Fun & Slutty. Van Ness promises a new and different take from what fans saw on Fun, considering the bleak current sociopolitical landscape. “It’s a lot of Republican stuff. It’s a lot of trans commentary on living as a gender-nonconforming person in this time,” Van Ness told GLAAD, describing their new material. “I’m also dealing more with racism than I ever have … white people … honey … we got to talk about it.” 8 p.m., Hard Rock Live, 6050 Universal Blvd., entertainment.hardrock.com, $48-$142.
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This article appears in Oct. 1-7, 2025.
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