Key West Headdress Ball

Thursday, October 22, 2026 · Coffee Butler Amphitheater at Truman Waterfront Park
Doors 6:30pm · Show 8:00pm

The Key West Business Guild presents the 43rd Anniversary Headdress Ball, one of the most anticipated nights of Fantasy Fest.

Legendary Key West entertainer Randy Roberts returns as host, with music by WEOW’s RudeGirl. Twelve to fifteen contestants take the stage to reveal their headdress creations — judged from the shoulders up — competing for a $2,500 grand prize.

New Award Categories

The Ball introduces six categories this year, recognizing different kinds of artistic achievement:

• Head Above the Rest — $2,500 · The night’s top honor, for the creation that best combines artistic vision, originality, craftsmanship, presentation, and overall impact
• Spirit of Fantasy Fest — $1,000 · For the creation that best captures the official Fantasy Fest theme
• Pretenders in Paradise — $750 · A nod to the beloved former Fantasy Fest costume competition, for the contestant whose costume and headdress read as one cohesive work
• Glow Getter — $500 · For the headdress that makes the biggest impact through creative illumination — LEDs, neon, or other lighting effects
• Dream Team — $500 · For two or more artists who combine their talents into a single, visually stunning presentation
• Size Doesn’t Matter — $500 · For the artist who makes a bold impression with a more compact design

Total prize purse: $6,000

Between competition rounds, the evening features performances by some of Key West’s most celebrated local entertainers. Full bar service and specialty wines are available, and food can be preordered and delivered right to your table.

Tickets

Prices do not include fees

• Premium Table for 4 — $400 (includes your choice of a bottle of wine, a bucket of beer, or non-alcoholic beverage selections)
• VIP Table for 4 — $290
• Reserved Chair Seating — $40
• General Admission, grass seating — $30

The Headdress Ball celebrates the artistic expression and inclusive spirit that have made Key West one of the world’s most distinctive destinations, and this night one of Fantasy Fest’s signature events.

This event sells out every year — reserve your seats early. For tickets, contestant information, or to enter the competition, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.

Schedule subject to change. Information courtesy of the Key West Business Guild — see their website for complete details.