With Key West’s picture-perfect year-round weather and spectacular outdoor scenery, our residents and visitors love to spend lots of time outdoors. And our small two-by-four-mile island has a number of unique city parks, so you’re never too far from your next outdoor adventure.

Fantasy Fest Headdress Ball Key West

This quirky and colorful “White Rabbit” ensemble took first place at the 2017 Headdress Ball held at the Key West Amphitheater at Truman Waterfront Park. (All photos by Peter Arnow)

The Truman Waterfront Park, located on the western tip of the island, is the newest addition to our park system and has stunning views of the harbor (and our legendary sunsets, of course).

The site was formerly Navy property that was given to the city and developed into the picturesque multi-use park in 2017. It now features a water park, children’s play area and an open-air amphitheater that’s an amazing oceanfront venue for concerts and community events.

I love attending events at the amphitheater, especially in the evening when there are two wonderful shows — one on the stage, and one in the skies above as Mother Nature produces another gorgeous Key West sunset.

One of my favorite events held at the amphitheater is the annual Headdress Ball, the premier LGBTQ event during our 10-day Fantasy Fest masking and costuming celebration.

The ball is produced each year by the Key West Business Guild, one of the United States’ oldest LGBTQ business organizations, and it’s one of their most successful fundraisers.

More than 25 entrants usually compete, wearing extravagant masks and towering headgear with over-the-top costumes decorated with feathers, sequins and creative accessories. Occasionally, entrants even stage elaborate sound and light shows to entertain their audiences!

In past years some of the headdresses have been so large that two stage-crew members had to help get the contestants up on stage. When I’ve ask entrants how long it takes them to construct their headdresses, some say only a few hours while others have spent months preparing their costumes.

Headdress Ball Fantasy Fest Key West

This elaborate multi-clock headdress illustrated Fantasy Fest’s 2017 theme, “Time Travel Unravels” and won second place.

The popular event offers cash prizes including a first-place award of $3,000. Most of the competitors are completely decked out from head to toe, though the panel of VIP judges is asked to rate the ensembles from the waist up only.

One of my favorite entries from last year’s event featured whirling visionary timepieces, in keeping with Fantasy Fest’s 2017 theme of “Time Travel Unravels.” This year’s theme is “Oh … The Games We Play!” and it should be equally inspiring.

The ball’s fabulous celebrity lineup includes the hilarious master of ceremonies Tom Luna, DJ Rude Girl and renowned female impersonator Christopher Peterson opening the show. The entertainment roster also includes Broadway veteran Terri White and female impersonator Randy Roberts, who always provide top-class entertainment between headdress performances.

The 36th annual ball starts at 8 p.m. on Thursday, Oct. 25. However, the gates open at 6:30 p.m., providing plenty of opportunities for attendees to enjoy food and libations offered for purchase before the show. It’s also a perfect 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 can pre-purchase food and refreshments to be delivered right to their table during the evening. The event sells out quickly, so I recommend buying your tickets ASAP — because this is one night you don’t want to miss.

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