Randal Lail of Key West took first place in the 38th Headdress Ball. The 39th is set for Oct. 27 at the Coffee Butler Amphitheater. PETER ARNOW/Contributed

“Cult Classics & Cartoon Chaos” is the theme for Fantasy Fest 2022 – Key West’s annual 10-day creative costumed festival. From Oct. 21-30, revelers can adorn themselves in creative attire, inspired by any TV show, film, cartoon or even book series with a cult following, and immerse themselves in an extravaganza of exciting and diverse events occurring islandwide — some classic fan favorites; some debuting for the first time this year.

The event was conceived in 1979 by local business owners Tony Falcone and Bill Conkle of Fast Buck Freddie’s fame and Key West Aloe founders Joe Lizska and Frank Romano as a remedy for Key West’s autumn island doldrums. In 2017 the event contract was awarded to We’ve Got the Keys, a Key West-based company headed by president/CEO Nadene Grossman Orr, who has been guiding the festival in its contemporary artistic and creative evolution. 

Here are some 2022 highlights. While the festival is aimed primarily at an adult audience, there are numerous events that are child/family-friendly. Complete information including times, locations, and contest entry links can be found at

A pleased pup disguised as a peacock takes center stage at a previous Pet Masquerade. This year’s event, open to furry, feathered, and even slithering critters, takes place on Wednesday, Oct. 26. CAROL TEDESCO/
  • Decorate your digs to win big. The Key West Chamber of Commerce Fantasy Façade contest offers cash prizes for the best-decorated Key West homes and businesses. Final day to enter is Oct. 17; judging is Monday, Oct. 24.
  • Oct. 13-27: “Bum Farto – the Musical” brings the infamous true story of Key West’s flamboyant drug-running 1970s-era fire chief to the San Carlos Institute.
  • Oct. 20 to Nov 12: “Jimmy Buffett’s Escape to Margaritaville – The Musical” at the Waterfront Playhouse presents a madcap love story, complete with an erupting volcano, tap dancing zombies and classic Buffett songs.
  • Oct. 21: The Royal Coronation Ball crowns Fantasy Fest’s 2022 King and Queen, 6 to 9:30 p.m. at the Coffee Butler Amphitheater.
  • Oct. 21 and 22: Bahama Village Goombay Festival (family-friendly) celebrates island arts and crafts, music and food in the historic Bahama Village neighborhood.
  • Oct. 22: The Seventh Annual Smallest Parade in the Universe, a fundraiser for the Monroe Association for Remarkable Citizens, showcases miniature parade floats on a replica of Duval Street. 7 p.m. at The Studios of Key West.
  • Oct. 24: Heroes & Villains Run/Walk 5K. Be super or be evil, but be active at this family-friendly, costumed event with awards and prizes. 6 p.m.
A group of Masquerade March revelers in 2018 portray Monopoly board game pieces and characters for an “Oh, the Games We Play” themed celebration. This year’s Captain Morgan Masquerade March is set for Friday, Oct. 28. CAROL TEDESCO/
  • Oct. 25: Florida Keys Council of the Arts hosts the official Fantasy Fest poster and t-shirt signing event. Get shirts and posters signed by winning artists Jack McDonald and Rick Worth. 3 to 5 p.m. at Wine-O inside La Concha Hotel. 
  • Oct. 26: Costume yourself and your critter(s) to compete in or just observe the always-adorable Pet Masquerade at Coffee Butler Amphitheater. Registration begins at 4 p.m., show at 6:30 p.m. Registration fees benefit Lower Keys Friends of Animals, Inc.
  • Oct. 27: The Annual Key West Headdress Ball, presented by the Key West Business Guild showcases an extravaganza of out-of-this-world headdresses modeled by their creators, along with exciting live entertainment. 8 p.m. at Coffee Butler Amphitheater.
  • Oct. 28: Strut your stuff in the Captain Morgan’s Masquerade March, as costumed creatives parade through Old Town, stopping for adult beverage samples provided by selected guest house along the route.Steps off at 5:30 p.m. Check website for location and route details.
  • Oct. 29: The world-famous Bud Light Fantasy Fest Parade features floats and costumed marching groups. Starts at 7 p.m. See website for route map.
  • Oct. 30: Don your fabulous feathers for “The Fat Lady Sings” Tea Dance from 4 to 8 p.m. at La Te Da on Duval Street — the final official Fantasy Fest celebration.
  • Oct 31: The 2023 Fantasy Fest theme will be announced. Start planning your costuming genius.

 For a full calendar of events, schedule updates and Fantasy Façade registration, visit

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