The Key West Business Guild presents the 35th annual Headdress Ball, the premier gay and lesbian event of the Fantasy Fest celebration, which proudly opens the brand new Key West Amphitheater at the Truman Waterfront  Park on Thursday, October 26 (Rain date is  Friday, October 27). This area was undamaged by Hurricane Irma.

They invite you to experience your favorite Fantasy Fest event in a new waterside setting and help Key West celebrate a beautiful expanded park system. Mayor Craig Cates will open the ceremonies and famed Key West Musician Howard Livingston will perform a special song he wrote for the occasion.  The colors will be presented by the military, and the Rainbow Flag by the Love is Love Foundation.

Tom Luna returns as the outrageous Emcee, and Rudegirl will again do the sound.  Randy Roberts opens the show and is joined by the best of Key West local talent, including Christopher Peterson, Sushi, Inga, and Elle Taylor throughout the contest.  Queen of Fantasy Fest contender Destiny Montgomery will render a special vocal performance.  Contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize, $1500 second place prize, and $500 third place award sponsored by Centennial Bank.

The show starts at 8 p.m., with the gates opening at 6:30 p.m. The Guild has retained its traditional four top table seating and expanded general admission area with last year’s pricing.  Bar service by the Aqua Night Club and SideBar featuring Stoli products. Blossoms Cajun Kitchen will have a food booth.

This popular event always sells out so book your tickets early on line at General Admission tickets are $30/person, with reserved tables for four people starting at $250.

The Key West Business Guild, one of the oldest LGBT Business organizations in the U.S., has produced the ball since its inception.  The event serves as a major annual fundraiser for the organization. For more information call the Guild at 305-204-4603 or visit