Revelers can showcase their most creative masks and outrageous headdress regalia at the 37th annual Headdress Ball happening on Thursday, Oct. 24, at the Key West Amphitheater located at Truman Waterfront Park. The highly anticipated ball is considered one of the highlights of the subtropical island’s annual 10-day Fantasy Fest celebration,offering spectators a unique blend of entertainment and imaginative pageantry. This year’s production is projected to draw an audience of some 500 people.

The gala typically features as many as 25 entrants. Wearing masks and innovative headgear creations — many with extravagant designs featuring feathers, sequins, exotic decorations or even mechanical elements — they compete for awards including a grand prize of $3,000.

“Our Headdress Ball is the premier LGBTQ event of Fantasy Fest,” said Kevin Theriault, executive director of the Key West Business Guild, which produces the event. “It’s a special evening of fabulous entertainment and a unique competition that allows contestants to impress the audience with what they’ve got from the shoulders up.”

The venue opens at 6:30 p.m., providing opportunities for audience members to purchase and enjoy food and beverages before the event begins at 8 p.m. Spectators also will have ample time to meet and photograph headdress entrants.

The evening’s all-star cast includes master of ceremonies Tom Luna, DJ Rude Girl and renowned entertainer Randy Roberts opening the show. Other local performers, including Christopher Peterson and the cast of the Waterfront Playhouse’s “The Rocky Horror Show,”are to offer stellar entertainment between headdress presentations.

General entry begins at $30 per person, with reserved tables for four people starting at $250. To purchase tickets, visit The Headdress Ball is a fundraising benefit for the Key West Business Guild, one of the oldest LGBT business organizations in the United States.

Event information:

Key West visitor information: or 1-800-LAST-KEY

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About the Author

Bryen Dunn is a freelance journalist based in Toronto with a focus on tourism, lifestyle, entertainment and community issues. He has written several travel articles and has an extensive portfolio of celebrity interviews with musicians, actors and other public personalities. He’s willing to take on any assignments of interest, attend parties with free booze, listen to rants, and travel the world in search of the great unknown. He’s eager to discover the new, remember the past, and look into the future.