The Key West Business Guild proudly presents the 43rd Anniversary Edition of the 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 stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize.

The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.

Ticket options: (does not include fees)
• Premium Table for 4 — $400( includes a bottle of wine of your choice, non-alcoholic drink option, or bucket of beer)
• VIP Table for 4 — $290
• Chair Seating — $40
• General Admission (Grass Seating) — $30

The Headdress Ball continues to celebrate the vibrant spirit, creativity, and welcoming atmosphere that makes Key West one of the world’s most unique destinations for visitors from all walks of life.

For more information, or to enter the Headdress Contest, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.