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The Weirdest Events at Fantasy Fest 2023

The Weirdest Events at Fantasy Fest 2023

October 5th, 2023 | Key West Events & Festivals

Fantasy Fest is known as a judgment-free zone where all things ‘weird’ are cause for celebration. Along with such freedoms come plenty of peculiar events for attendees. Here we’ve rounded up this year’s weirdest events at Fantasy Fest “Uniforms and Unicorns,” which runs Oct. 20-29, 2023.

Although we strive to provide the most current information, events mentioned may be canceled without notice. We recommend checking individual event websites for updates before attending.

[Book Direct with The Gates Hotel and Save up to 25% on your Key West Stay Only When You Click Here]

The Rocky Horror Show, The Musical - Wednesday, Oct. 18 - Friday, Oct. 27, 8 p.m.

Musicals can get pretty weird, and the sci-fi comedy horror musical that is The Rocky Horror Show proves it. The live stage performance of the cult classic is back at Waterfront Playhouse (407 Wall St.) during Fantasy Fest. Tickets are $65.

Zombie Bike Ride - Sunday, Oct. 22, 6 p.m.

Join your fellow newly awakened zombies at Fort East Martello at 2 p.m. for a family-friendly party with body painting, food vendors, and a full bar. Afterwards, join thousands of zombies as they hop on their bicycles for the 6 p.m. ride to the free Zombiefest Dance Party at the Coffee Butler Amphitheater. Registration is $10.

The Gates Hotel is excited to be hosting Zombie Zone - A Red Carpet Event where zombies are invited to walk the red carpet, show off their Zombie Bike Ride costume, and dance with the dead before the big ride. The official Fantasy Fest event includes free bike parking, live music, and food and drink specials. Free and open to the public. Sunday, Oct. 22, 12 - 6 p.m.

Best Beard Championship, The Phlocking Parrot Head Edition - Monday, Oct. 23, 4 p.m.

Build the wackiest beard and mustache you can think of, or grow your own and decorate it to the max, and show up at Willie’s Chicken Shack (221 Duval St) to win prizes. This year’s contest is dedicated to Jimmy Buffett and includes a stage show, victory celebration, and live music. Register ahead for $5.

Heroes and Villains 5K - Monday, Oct. 23, 6 p.m.

Dress up as your favorite superhero or supervillain for a run/walk (or fly) to the finish line. The 5K starts and ends near the beach at the Southernmost Beach Resort parking lot (506 South St.). After a race through Old Town, join other caped superheroes/villains at the on-site Hog Roast Beach Party or the annual Comic Book Cape-ers party at Sloppy Joe’s. Tickets to Heroes and Villains begin at $49.99.

Pirates of the Conch Republic: The Search for Bodacious Booty, a Burlesque Parody - Monday, Oct. 23 - Friday, Oct. 27, 8 p.m.

The sexy, swashbuckling spectacular at the Key West Theater (512 Eaton St.) follows Captain Jack on his epic adventure to find a bounty of bodacious booty. The nightly show stars local burlesque performers. Tickets begin at $45.

Kinky Carnival - Monday, Oct. 23, 8 p.m. - 1 a.m.

Now in its 26th year, the Kinky Carnival includes interactive BDSM stations, fetish rooms, bondage, and a 3-hour open bar. Dress in your kinkiest costume and join others at First Flight (301 Whitehead St.) for the festivities. Tickets are $50. No kinky costume, no entry!


TuTu Tuesday - Tuesday, Oct. 24, 6 p.m. - 3 a.m.

Tuesday has never been better. Grab your tutu, be the most daring dancer, and celebrate all things “tutu” with this year’s theme “Follow the Yellow Brick Road.” The 13th annual party takes place throughout the Caroline District with nearly 20 DJs and four premium bars participating in this year’s festivities - General Horseplay, Smokin’ Tuna, First Flight Brewery, and Hanks Hair of the Dog Saloon. Presale tickets are on sale now for $22 and the party is 21+. No tutu, no entry!

Cocktails for Animal Tails - Tuesday, Oct. 24, 8 p.m. - 4 a.m.

A good cause that is bizarre enough only for Fantasy Fest. Each bar at Rick’s Complex (202 Duval St.) will be transformed into different animal kingdoms and guests are urged to get in touch with their wild side and come dressed as their favorite animal for the $500 grand prize costume contest. The all-you-can-drink animal party benefits the FL Keys SPCA. Tickets are $40.

Masquerade March - Friday, Oct. 27, 5:30 p.m.

The popular adults-only moving cocktail and dance party highlights costumes, creativity, and community. Beginning at Old Town Wine & Spirits on Truman Avenue, the procession stops at 12 participating businesses along the way for revelers to enjoy complimentary beverages and strut their wacky costumes before ending on Duval Street. The event is free!

Unicorns Only Party - Friday, Oct. 27, 8 p.m.

In keeping with this year’s ‘Uniforms and Unicorns’ theme, Fantasy Fest 2023 has its share of on-brand festivities, but none like Unicorns Only. For one, you “must be a unicorn to enter” the magically enchanted forest at Big Cheezees Pub & Grub at 404 Southard Street. Mingle with unicorns and listen to beats by DJ Hazard. Tickets are $35 and include one drink, pizza, and a donation made to the Key West Police Department Love Fund. 

Looking to put your one-horned costume to more use? The Unicorns and Tequila Pool Party on Thursday, Oct. 26 from 12 - 4 p.m. at Havana Cabana will have glittering drink specials and unicorn rides, and Side Bar’s Save A Unicorn, Ride A Cowboy party with DJ Honey Davenport is Saturday, Oct. 28 at 9 p.m. following the Fantasy Fest Parade.

[Excited for the Fantasy Fest Parade? Here are the best places to watch from]

“The Fat Lady Sings” Tea Dance - Sunday, Oct. 29, 4 - 8 p.m. 

The last official event of Fantasy Fest is a hurrah like no other. DJ Rude Girl supplies the beats in one last epic party at La Te Da before the festival’s official closing, which is taken directly from the colloquialism “It ain't over till the fat lady sings." Tickets are $5.



The Gates Hotel offers guests shuttle service to Old Town, so you don't have to worry about transportation woes during Fantasy Fest. Plus, you have an oasis with excellent amenities - like an on-site food truck, cigar lounge, and a spectacular swimming pool. Check out our special offers online.

See what our past Fantasy Fest guests are saying about us:

“Stayed here for Fantasy Fest. The Gates Hotel had a shuttle on the 1/2 hour that was great as it took you down to the action.” - Thomas M., TripAdvisor

“The Gates Hotel became a favorite of mine..And I make it a point to stay here whenever I visit Key West. Usually for Fantasy Fest. It's charming…Quieter than the other resorts…It has a wonderful laid back, tropical, throwback ambiance to it, that I love so much…I'll keep coming back.” - Eric, TripAdvisor

“I booked…during the week of Fantasy Fest. The Gates Hotel was affordable and just far enough away from Duval Street...The Pool was a great place to relax and get some work done. There is a pool bar and wait staff on hand to keep us hydrated…They provided a free shuttle to downtown and it ran until midnight. That's a great benefit when you're in Key West. Overall this was a great hotel and I would definitely stay again.” - Loco Gringo, TripAdvisor