Nothing says “Fantasy Fest®” more than feathers, glitter and glue and you’re bound to see a lot of it during the 37th Annual Headdress Ball on Thursday, October 24.

Sure, there are tons of great costume parties during Fantasy Fest® week but nothing can top Key West’s annual Headdress Ball. This one is literally heads above the rest and includes incredibly elaborate masks and headdresses that can take weeks to create.

With a first-place award of $3,000, contestants are judged only from the head up. Emceed by local actor and funny-man, Tom Luna, this off-the-charts annual fund-raiser for the Key West Business Guild, (the nation’s oldest gay and Lesbian Chamber of Commerce) is one fantastical night.

In addition to the 25+ contestants, female illusionists Randy Roberts and Christopher Peterson will take to the stage along with several other highly acclaimed performers, including Broadway diva, Terri White.

Local vendors, food by Great Events Catering, and bar service by Aqua Nightclub and Sidebar round out the party.

Takes place at the Key West Amphitheater at Truman Waterfront Park. Gates open at 6:30pm with showtime at 8pm. Info: 305-294-4603; Tickets: