Headdress Ball to Top Key West’s Entertainment Roster Oct. 24

KEY WEST, Florida Keys — Revelers can showcase their most creative masks and outrageous headdress regalia at the annual Headdress Ball slated for Thursday, Oct. 24, at the Coffee Butler Amphitheater located in Key West’s Truman Waterfront Park.

The much-anticipated event is a highlight of the subtropical island’s 10-day Fantasy Fest, a lavish costuming and masking celebration set for Friday, Oct. 18, through Sunday, Oct. 27. 

Now in its 41st year, the headdress gala offers spectators a unique blend of entertainment, imaginative pageantry and unparalleled design ingenuity. 

The competition typically features more than 15 entrants wearing masks and innovative headgear creations — many of them featuring feathers, sequins, exotic decorations or even moving parts. 

Taking turns displaying their creations onstage, contestants compete for awards including a grand prize of $3,000. Although most are costumed from head to toe, they are judged from the shoulders up to focus on their headdresses.

The evening is to star acclaimed Key West female impersonator Randy Roberts as master of ceremonies, with popular DJ Rude Girl overseeing musical selections. Other local performers are to offer stellar entertainment between headdress presentations.

“The Headdress Ball is Fantasy Fest’s premier LGBTQ event,” said Rob Dougherty, executive director of the Key West Business Guild that produces the event. “Audience members can expect an amazing night filled with talent, creativity and maybe a little camp.”

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. 

General admission begins at $30 per person, with reserved VIP tables for four people starting at $270. To purchase tickets, visit https://keystix.com. Libations and food service can be ordered with ticket purchases. 

The Headdress Ball is a fundraising benefit for the not-for-profit Key West Business Guild, a widely renowned LGBTQ business organization founded in 1978. The guild supports Key West’s gay and gay-friendly enterprises, local community and position as an internationally recognized LGBTQ vacation spot.

Event information: gaykeywestfl.com/headdress-ball/