The Key West Business Guild proudly presents the 42nd Anniversary Edition of the Headdress Ball, the premier LGBTQ+ event of the Fantasy Fest Celebration, presented on Thursday, October 23, 2025, at the Coffee Butler Amphitheater, Truman Waterfront Park.
Doors open at 6:30 and the show begins at 8:00 PM.
Popular Key West entertainer, Randy Roberts will emcee and arrange the show this year. WEOW’s Rudegirl oversees the music. Twelve to Fifteen contestants will hit the stage to show their Headdress creations, judged from the shoulders up, and vie for the first prize of $5,000! Performances by some of Key West’s best local talent from over the years will again be featured. There is bar service and specialty wine; food may be preordered and delivered to your table. Tickets are $320 for a premium table of 4, $270 for a VIP table of 4, with Chair seating at $35 and General Admission (grass seating) at $30. Admission and food choices may be booked at: www.keystix.com.
Proceeds from the Headdress Ball help to promote Key West as a major LGBTQ+ destination worldwide.
For more information, and to enter the Headdress Contest, go to gaykeywestfl.com/headdress-ball or call 305-294-4603.
This event always sells out so book your tickets early.
