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October 24, 2019

37th Annual Headdress Ball

Gates Open 6:30 pm. Show begins 8 pm. Key West Amphitheater.

The Key West Business Guild presents the 37th annual Headdress Ball on Thursday, October 24, 2019 at 8 pm. This premier gay and lesbian event of the Fantasy Fest celebration proudly returns to the new Key West Amphitheater at the Truman Waterfront Park.

Tom Luna returns as the outrageous EmCee with Rude Girl rocking out our sound. Christopher Peterson opens the show and is joined by some of the best of Key West local talent, including Randy Roberts and Terri White, throughout the contest. Over twenty five contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize.

The Guild has retained its traditional four-top table seating and expanded General Admission on the rear raised grass area. There will be waiter and bar service by Aqua/Sidebar featuring Stoli products. For the first time, table purchasers can preorder on keystix a premium white/red/champagne wine from Aqua/Sidebar and/or a food box from Great Events to be delivered to their table that evening. Come experience your favorite Fantasy Fest event in a new waterside setting and help Key West celebrate a beautiful expanded park system.

Interesting in competing?

This unique competition allows contestants to go “head to head” to impress the audience with what they’ve got from the shoulders up! This is the first year that the VIP audience will participate in the judging.

Prizes for Best Headdress: $3,000, $1,000 second, $500 third.

This is a Headdress competition and as such costumes are not considered in the awarding of points. Though the audience enjoys fully costumed entries, please note that the Judging will be done from the shoulders up!

Entries can include costumed “spotters” however the physical presence of the spotters cannot be required for the support of the headdress.

There is no admission fee for those entering the Headdress Ball competition.

Register here!


Key West
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