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The Weirdest Events at Fantasy Fest 2021

The Weirdest Events at Fantasy Fest 2021

September 30th, 2021 | 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 of Fantasy Fest “All a Daze for a Holiday,” which runs Oct. 22-31, 2021.

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

Heroes and Villains Run/Walk 5K - Monday, Oct. 25 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.

Kinky Carnival - Monday, Oct. 25 at 8 p.m.

Now in its 24th 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 $60. Visit the Fantasy Fest website for some costume inspiration.

12th Annual TuTu Tuesday - Tuesday, Oct. 26 at 7 p.m.

Tuesday has never been better. Grab your tutu and celebrate all things tutu at Aqua, 22&Co., and Sidebar (711 Duval St. and 504 Angela St.). Wristband entry is $40 ($50 at the door) and the party is 21+. No tutu, no entry!

Harriette Potter and the Enchanted Tassel: A Burlesque Parody - Tuesday, Oct. 26 - Friday, Oct. 29 at 8 p.m.

Enter the wizarding world of Harriette Potter and the Enchanted Tassel, a burlesque parody that leads you on a salacious search for a magical, missing tassel. Tickets to the saucy show at the Key West Theater (512 Eaton St.) start at $50.

Masquerade March - Friday, Oct. 29 at 5:30 p.m.

The Fantasy Fest Parade may be cancelled, but the Masquerade March is the next best thing. The popular, adults-only moving cocktail and dance party highlights costumes, creativity, and community. Beginning at the entrance to the Key West Cemetery on Frances Street, 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 travel plans. Plus, you have an oasis with excellent amenities – like food truck access, a cigar lounge, and a spectacular swimming pool. Check out our special offers online.

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