Fantasy Fest 2026 Welcomes Revelers to Center Stage with “Musical Icons and Iconic Musicals” Theme

Fantasy Fest, Key West, Florida’s annual multi-day costuming party in paradise, welcomes revelers from near and far to turn the island into a living celebration of musical spectacle during this year’s extravaganza, set for October 16-25.

The 2026 Fantasy Fest theme, “Musical Icons and Iconic Musicals” invites fantasy-makers to style themselves at the center of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic, or take center stage as the musical icon – or iconic musical character – of their dreams. The sky’s no limit for this “Swift-ly” moving and “Wicked-ly” wondrous ten-day break from the ordinary.

Here’s a sampling of just some of this year’s highlights. Complete information for events, times, locations, and contest entry links can be found at http://www.fantasyfest.com:

• Fantasy Façades Contest: Creatively transform your home or business for a chance to win cash prizes ranging from $100-$1000. Reflect this year’s theme or channel traditional Halloween ghoulishness! Entry form available Sept. 1; deadline to enter Oct 12.

 

• Oct. 16: The Royal Coronation event to crown Fantasy Fest’s 2026 King and Queen is a dazzling 2-hour stage show at the Coffee Butler Amphitheater that features performances by the intrepid competitors along with local celebrities. Proceeds benefit the Florida Keys SPCA.

 

• Oct. 16 and 17: The Bahama Village Goombay Festival is a two-day, family friendly celebration of island arts and crafts, culture, music and food held throughout Key West’s historic Bahama Village neighborhood.

 

• Oct. 18: That Arena Rock Show at Sunset Pier: A free admission, high-energy, time-traveling theatrical tribute to classic Rock & Roll.

 

• Oct. 19: Mrs. Roper’s Romp: Break out your colorful caftan and signature curly red wig for a groovy “Three’s Company” inspired party at Sunset Pier filled with music, photo ops, dancing, games, and prizes.

 

• Oct. 19: A Green Parrot Beatles Tribute: Jump into your yellow submarine and disembark in the 1960’s for this dress-up dance party with Key West’s very own Beatles tribute band.

 

• Oct. 20: Florida Keys Council of the Arts Fantasy Fest poster-signing party at the La Concha Hotel: Meet the artist, get your poster signed, and stock up on other collectable Fantasy Fest 2026 t-shirts and swag.

 

• Oct. 20: Tutu Tuesday with its annual epic dance party features lights, lasers, and multiple dynamic DJ’s spinning at four different Caroline St. district area venues. Tutu’s required!

 

• Oct. 21: LUV2GLOW PARTY – Rick’s Upstairs on Duval Street transforms into a vibrant universe of fluorescent visuals, underwater-inspired décor, and pulsating house music with immersive glowing environments, DJ’s and live performers. Come dressed or painted to glow under black-lights.

 

• Oct. 21: Pet Masquerade, presented by Florida Keys Media at the Coffee Butler Amphitheater: Costume up with your favorite critter friends at this over the top competition or cheer them on from the audience. Prizes in multiple categories; registration fees benefit the Monroe County Sheriff’s Office Animal Farm.

 

• Oct. 22: The 42nd Annual Key West Headdress Ball, presented by the Key West Business Guild at the Coffee Butler Amphitheater reveals a playlist of out-of-this-world headdresses modeled by their creators along with high-energy entertainment by some of the island’s best talent.

 

• Oct. 22: Sloppy Joe’s 47th Annual Toga Party: Live music starts early and flows late at this revelry, where fantasy-makers can don traditional Roman “drape duds” or create their own 2026 Fantasy Fest theme-inspired versions. Toga costume contest welcomes individuals or groups of 2-4.

 

• Oct. 23: Paparazzi Row is the place to get warmed up and strut your stuff for the camera’s ahead of the Captain Morgan Masquerade March. Dance music will play and local paparazzi, photo booths and selfie stations will be set up to record epic costumed crews.

 

• Oct. 23: The Captain Morgan Masquerade March (aka “Local’s Parade”) brings all creative hands on deck as costumed revelers parade through Old Town Key West, stopping along the route for adult beverage samples provided by selected guest houses.

 

• Oct. 23 and 24: The magnificent mile-long Fantasy Fest Street Fair and Costume Promenade offers revelers an extravaganza of fabulous food, lively libations, arts, crafts and costumes starting at high noon and going into the night.

 

• Oct. 24: The world famous Deep Eddy Vodka Fantasy Fest Parade in Old Town Key West presents a dazzling array of fabulous floats, magnificent marching groups, and cool kinetic contraptions to bring this year’s “Musical Icons and Iconic Musicals” theme to life. An awesome island tradition since 1979!

 

•  Oct. 25: Children’s Day at Bayview Park offers a daytime fest from noon to 5:00pm with games, food, rides, entertainment, arts & crafts, and a costume contest for the kids.

 

• Oct. 25: Don your fabulous feathers for “The Fat Lady Sings” Tea Dance at La Te Da on Duval Street—the final official Fantasy Fest celebration.

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• Oct 26: The 2026 Fantasy Fest theme will be announced.

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“At Fantasy Fest, you can see the spectacle and be the spectacle,” said Fantasy Fest Director Nadene Grossman Orr. “Whether you arrive as a Broadway legend, rock icon, pop superstar, or icon of your own creation, this is your invitation to step into the spotlight and let your imagination take flight.”

Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, schedule updates, contest details, and a downloadable mobile APP, visit http://www.fantasyfest.com.