Key West Headdress Ball

Every Fantasy Fest, Key West stages the Headdress Ball, a competition built entirely around what contestants can create from the shoulders up. The 2026 edition marks its 43rd year, running Thursday, October 22, with doors at 6:30 p.m. and the show starting at 8 p.m. at the Coffee Butler Amphitheater in Truman Waterfront Park.

What to expect

Twelve to fifteen contestants take the stage in elaborate, often architecturally ambitious headdresses, judged purely on the creation itself rather than a full costume. Legendary Key West entertainer Randy Roberts hosts, with music from WEOW's RudeGirl running the night. A $2,500 grand prize goes to the winning design, with new award categories added this year recognizing different kinds of artistic craft beyond just the top prize.

History and legacy

Presented annually by the Key West Business Guild, the Headdress Ball has run since the early 1980s and sits among the most anticipated single nights of the entire Fantasy Fest calendar. Its format, judging creativity from the shoulders up rather than a full costume, gives it a distinct identity within a festival otherwise built around elaborate full-body looks.

Getting there

The Coffee Butler Amphitheater sits within Truman Waterfront Park, a short distance from Key West's main Duval Street strip. Given the crowds Fantasy Fest draws island-wide, arriving early for a good seat is worth doing regardless of how you get there.

Plan your trip

The Headdress Ball falls in the middle of Fantasy Fest's ten-day run, so it's easy to build a full island stay around it rather than visiting for a single night. Book accommodation well ahead, since Fantasy Fest week is one of Key West's busiest of the year across the board.