Home Features The 36th Annual Headdress Ball Comes to Key West

The 36th Annual Headdress Ball Comes to Key West

Combining entertainment and creative rivalry, Key West’s Headdress Ball typically dazzles audiences with contestants’ flamboyant masks and outrageous headdress regalia. The 36th annual ball is set for 8 pm Thursday, Oct. 25, at the Key West Amphitheater at Truman Waterfront Park. 

The gala is the premier LGBTQ event of the subtropical island’s 10-day Fantasy Fest celebration. 

More than 25 entrants wearing masks and headgear constructions — many decorated with feathers, sequins, unique accessories or even moving parts — are expected to vie for cash prizes including a first-place award of $3,000. While some competitors wear full costumes, the panel of VIP judges evaluates ensembles only from the shoulders up.

The ball is produced each year by the Key West Business Guild, one of the United States’ oldest LGBTQ business organizations, and serves as a major fundraiser for it.

“The Headdress Ball will be an evening of creativity, fun and surprise guest entertainment taking place during the competition — something you won’t want to miss,” said Dan Skahen, the guild’s executive director.

The celebrity lineup includes master of ceremonies Tom Luna, DJ Rude Girl and renowned female impersonator Christopher Peterson opening the show. Talents including Broadway veteran Terri White and female impersonator Randy Roberts are to offer top-class entertainment between headdress performances.

Gates open at 6:30 p.m., providing opportunities for attendees to enjoy food and beverages offered for purchase by local vendors before the show. Spectators also will have ample time for mingling and photo ops with the headdress entrants.

General admission tickets are $30 per person, with reserved tables for four people starting at $250. Reserved table holders may pre-purchase food and refreshments to be delivered to their table during the evening.   

Event and ticketing information: headdressballkeywest.com, gaykeywestfl.com, fantasyfest.com.

Key West visitor information: fla-keys.com/keywest or 1-800-LAST-KEY.

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