Thursday, September 28, 2023

Key West’s 40th Annual Headdress Ball to Dazzle Spectators Oct. 26

The 40th annual Headdress Ball, an over-the-top showcase for mask-makers and costumers, is to take place Thursday, Oct. 26, at Key West’s Coffee Butler Amphitheater in Truman Waterfront Park.  

Celebrating the creative and entertaining spirt of Fantasy Fest, the island’s 10-day costuming and masking festival set for Oct. 20-29, the Headdress Ball is the festival’s premier LGBTQ event. Plans call for it to feature 12 to 15 contestants, all wowing the audience with unique headdresses — even some featuring moving parts or towering high above their wearers. 

Although most participants are costumed from head to toe, entrants will be judged only from the shoulders up as they vie for the first-place prize of $3,000.

As well as headdress presentations, audiences can enjoy entertainment by local talents including nationally acclaimed female impersonator Randy Roberts. Key West’s Laurie Thibaud is to emcee, with music overseen by DJ Rude Girl.

Ticketholders will be welcomed to the amphitheater at 6:30 p.m., providing ample time for them to mingle and take photos with entrants before the show begins at 8 p.m.

Spectators also can enjoy bar and wine service and have preordered food delivered to their table during the event.

The Headdress Ball has been produced for the past 40 years by the Key West Business Guild, one of the oldest LGBTQ business organizations in the United States. Proceeds from the event help the guild support Key West’s gay and gay-friendly enterprises, community and the island’s position as a leading LGBTQ vacation spot. 

Tickets are $320 for a premium table for four people, $270 for a VIP table for four, $35 per person for chair seating and $30 per person for general admission with lawn seating. To purchase tickets and preorder food, visit