Key West Headdress Ball – 43rd Anniversary Edition

Key West Headdress Ball 2026 at Coffee Butler Amphitheater

The 43rd Annual Key West Headdress Ball takes center stage on Thursday, October 22, 2026, transforming the Coffee Butler Amphitheater at Truman Waterfront Park into a dazzling celebration of artistry and LGBTQ+ pride. Known as the crown jewel of Fantasy Fest, this spectacular evening blends creativity, theatrical performances, and island flair into one unforgettable event.

Hosted by the legendary Randy Roberts, with beats by WEOW’s Rudegirl, the night promises jaw-dropping entertainment and vibrant energy from start to finish. The highlight of the evening is the Headdress Competition, featuring 12–15 contestants showcasing elaborate shoulder-up masterpieces. Designers and performers will compete for a grand prize of $5,000, along with additional awards for standout creations.

Guests can enjoy more than just the show—live performances, a full bar and specialty wine service, and the option to pre-order dining delivered to your table create a complete Key West experience.

Ticket options ensure everyone can be part of the excitement. Choose from Premium Tables ($320 for four seats), VIP Tables ($270 for four seats), Chair Seating ($35), or General Admission on the lawn ($30). With limited availability and a history of selling out each year, early reservations are highly recommended.

🎟 Tickets and dining reservations are available at keystix.com. For contestant entry details, visit gaykeywestfl.com/headdress-ball or call 305-294-4603. Proceeds benefit the Key West Business Guild, supporting the promotion of the island as a premier LGBTQ+ destination worldwide.

Mark the calendar for an evening under the stars where creativity reigns supreme—the Key West Headdress Ball is a Fantasy Fest tradition not to be missed.

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