43rd Anniversary of the Headdress Ball 2026 — live event on Oct 22, 2026
43rd Anniversary of the Headdress Ball 2026 at Coffee Butler Amphitheater, Key West on Thu, Oct 22, 8:00 PM. Free entry. Lineup, start time and tickets on Ckord.
The Key West Business Guild proudly presents the 43rd Anniversary Headdress Ball, one of the most anticipated events of the Fantasy Fest celebration, on Thursday, October 22, 2026, at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM, with the show beginning at 8:00 PM. This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW's RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their spectacular headdress creations, judged from the shoulders up—as they compete for the coveted $2,500 Grand Prize. New this year, the Headdress Ball introduces several exciting award categories that celebrate every aspect of artistic excellence and imagination: Head Above the Rest Award – The competition's highest honor, recognizing the contestant whose creation best combines artistic vision, originality, craftsmanship, cre…
Starts: Thu, Oct 22, 8:00 PM
Ends: Thu, Oct 22, 10:00 PM
Where: 21 Quay Road, Key West, Florida 33040, United States
Price: $0.0
Venue: Coffee Butler Amphitheater
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