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Ticket Sales begin July 1st -Purchase tickets @ Keystix.com

Key West Headdress Ball

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 is the premier LGBTQ+  event of the Fantasy Fest celebration  and the event proudly returns to the new Key West Amphitheater at the Truman Waterfront Park.

Tom Luna returns as the outrageous EmCee with Rude Girl from WEOW 92.7 radio rocking out our sound. Randy Roberts will open the show and is joined by some of the best of Key West local talent, including Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show! Over twenty  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. VIP wine and food can be pre-ordered by contacting [email protected] or call 708-921-9584 Come experience your favorite Fantasy Fest event in a new waterside setting and help Key West celebrate a beautiful expanded park system.


To advertise in the Headdress Ball Program – please call 305-292-7963


Tickets are available for purchase July, 1 2019 by visiting Keystix.com

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!Contestants preregistered for the competition by September 20, 2019 will be listed in the Headdress Ball program. Note to contestants – please be advised that the Headdresses must be worn on the head during the competition. Contestants may have an assistant on stage if needed.

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!


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