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42nd Anniversary Headdress Ball

Date/Time

October 23, 2025
8:00 pm - 10:00 pm

Location

Coffee Butler Amphitheater
21 East Quay Road, Key West, Florida, 33040

Event content

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.