Every year in October, there’s a tidal wave of gossip flowing in Key West. The top-secret chatter du jour is mostly costume-related as visitors and locals alike get their creative juices flowing and glue guns powered up — all hoping to create the winning headgear for our annual Headdress Ball.
The 37-year-old gala will be held Thursday, Oct. 24, at the scenic Key West Amphitheater located at Truman Waterfront Park. The theater’s stage is set in a stunning location, with shimmering blue-green waters and majestic palm trees as its backdrop.
The highly anticipated event is one of the highlights of Key West’s annual 10-day Fantasy Fest celebration. I’m often asked what Fantasy Fest festivities are like, and I think the best way to describe them is “a bit like Mardi Gras in New Orleans but with a zany island-style twist.” (And there are some classic Key West characters added to the mix, of course).
The Headdress Ball offers spectators a unique blend of entertainment and imaginative pageantry, which is a perfect fit for our Fantasy Fest revelries. This year it’s expected to draw an audience of over 500 people and will have an expanded viewing area to accommodate everyone.
The show features more than 20 extraordinarily creative entrants with non-stop entertainment that never disappoints the cheering crowds. Wearing lavish 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.
Over the years, I’ve seen so many amazing headdress entries, with some taking up a startlingly large space and requiring several volunteers just to get them on and off the stage. Some of my past faves included over-the-top laser light shows and smoke machines, and were choreographed to the nines.
“Our Headdress Ball is the premier LGBTQ event of Fantasy Fest,” said Kevin Theriault, executive director of the Key West Business Guild that 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 enchanting outdoor venue opens at 6:30 p.m., providing opportunities for audience members to purchase some tasty nibbles and adult libations before the show gets underway at 8 p.m.
Headdress fans will also have ample time to meet and photograph the contestants all decked out in their towering creations. It’s also a perfect opportunity for “selfie fanatics” to rack up those likes and shares on their social media pages.
The evening’s all-star cast includes the hilarious master of ceremonies Tom Luna, DJ extraordinaire Rude Girl and renowned entertainer Randy Roberts opening the show. Also performing will be the ever-so-talented female impersonator Christopher Peterson and the cast of the Waterfront Playhouse’s “The Rocky Horror Show,” engaging audiences between headdress presentations.
The Headdress Ball producer, the Key West Business Guild, is one of the oldest LGBTQ business organizations in the United States. The residents of Key West are incredibly proud of the guild’s accomplishments and thankful for its ts continuous efforts to help our island’s “One Human Family” community flourish.
General entry begins at $30 per person, with reserved tables for four people starting at $250. To purchase tickets, please visit keystix.ticketforce.com — and do it soon, because this over-the-top event is likely to be a sell-out.
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