The Key West
Annual Headdress Ball 2024

The Key West Annual Headdress Ball 2024

The Key West Headdress Ball is the premier gay and lesbian event of the Fantasy Fest celebration.

• Visiting for the event? If you are looking for a last minute deal or want a larger hotel with great amenities, check out the Key West Marriott Beachside. Alternatively try Alexander’s Guesthouse  for a unique gay escape.

The Competition

• This unusual competition allows contestants to go “head to head” to impress the audience with what they’ve got from the shoulders up!
• Over twenty five contestants will parade their Headdress creations to vie for the $3,000 first prize.

The 2024 Annual Headdress Ball

• Next edition – Thursday, October 24th, 2024
• The ball begins at 8 PM. The event is held at the Coffee Butler amphitheater at Truman Waterfront Park, a 4 minute drive from the bars along Duval street.
• First Place prize is $3,000; Second Place is $1000, and Third Place is $ 500 for the best Headdresses, judged from the shoulders up.
• La Te Da’s Randy Roberts opens the show and Laurie Thibaud of Aqua Idol Fame returns as the Emcee. WEOW’s Rudegirl oversees the music.
• Proceeds from the Headdress Ball go to promote LBGTQ+ Tourism to Key West. Following the show there will be a special Happy Hour Disco Dance at the Aqua Sidebar.

History of the event

• Over three decades ago a group of Key West business people gathered together to form the Key West Business Guild, the nation’s oldest LGBT Chamber of Commerce.
• Only a few years later during the fledgling years of Fantasy Fest, that same group started the Headdress Ball. The Ball served then, as it does now, as a major fundraiser for the Guild.

Gay Key West – Where to stay?

Most of the gay bars in town are clustered along colourful Duval Street. Check out our Gay Guide to Key West.

The following hotels are close to the gay bars and beaches:

Duval Gardens,    Truman Hotel,    The Gardens Hotel,    Paradise Inn