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The Weirdest Events at Fantasy Fest 2022

The Weirdest Events at Fantasy Fest 2022

August 30th, 2022 | 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 “Cult Classics & Cartoon Chaos,” which runs Oct. 21-30, 2022.

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.

Bum Farto: The Musical - Thursday, Oct. 13 through Thursday, Oct. 27 at 8 p.m.

Key West’s former Fire-Chief-turned-fugitive is the subject of this wild musical. After a scuffle with the law in the late 70s, the flamboyant Joseph “Bum” Farto (known for his trademark red leisure suits, flashy gold chains, and rose-colored glasses) fled from the law, and was never seen again. Dancers, actors, and singers tell the story of the infamous Fire Chief through authentic Cuban styles. Tickets to the show at the San Carlos Institute (516 Duval St.) start at $35.

For more on Key West’s infamous Fire Chief, check out this fun profile of Bum Farto from our sister hotel, 24 North.

Jimmy Buffett’s Escape to Margaritaville: The Musical - Thursday, Oct. 20 through Saturday, Nov. 12 at 8 p.m.

Jimmy Buffett’s rom-com musical comes to Key West, and in true ‘Margaritaville’ fashion, gets a little weird. With a heaping dose of Buffett’s most popular tunes, the musical gets downright goofy at times, with segments involving dancing insurance salesmen zombies, a “Why Don’t We Get Drunk” sing-along, and more off-beat details only Buffett can pull off. ‘Escape to Margaritaville’ is always a good time! Tickets to the show at the Waterfront Playhouse (310 Wall St.) start at $40.

Smallest Parade in the Universe - Saturday, Oct. 22 at 7 p.m.

In stark contrast to the wild Fantasy Fest Parade on Saturday, Oct. 29, the Smallest Parade in the Universe is a much quieter affair. Guests are invited to design their own Fantasy Fest-themed mini float (no bigger than a shoebox) to take part in the procession. Watch the entire parade from the Studios of Key West at 7 p.m. Floats are auctioned off afterwards to benefit MARC, the Monroe Association for ReMARCable Citizens.

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

Heroes and Villains Run/Walk 5K - Monday, Oct. 24 at 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 your fellow caped superheroes/villains at Sloppy Joe’s for their Comic Book Cape-ers party. The party starts at 8 p.m. Register ahead.

Kinky Carnival - Monday, Oct. 24 at 8 p.m.

Now in its 25th 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. Visit the Fantasy Fest website for some costume inspiration. Costumes required!

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

TuTu Tuesday - Tuesday, Oct. 25 at 7 p.m.

Tuesday has never been better. Grab your tutu, be the most daring dancer, and celebrate all things “tutu” with multiple DJs at Aqua, 22&Co., and Sidebar (711 Duval St. and 504 Angela St.). In-person presale tickets are on sale now in Key West for $22 (online tickets will be available Oct. 1) and the party is 21+. No tutu, no entry!

She-Avengers Stripfinity Wars: A Burlesque Parody - Tuesday, Oct. 25 through Friday, Oct. 28 at 8 p.m.

The stripping superhero team She-Avengers take on the powerful Fanos in order to protect the powerful Stripfinity Stones! You don’t want to miss this burlesque parody, which takes place in a different, much weirder, dimension of the multiverse. Tickets to the saucy show at the Key West Theater (512 Eaton St.) start at $55.

Masquerade March - Friday, Oct. 28 at 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 participating guest houses for complimentary beverages before ending on Duval Street.



The Gates Hotel offers free hourly 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 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

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