Southard Street, Key West, FL, United States


  • Pride
  • Party

The Headdress Ball is the premier gay and lesbian event of the annual Fantasyfest. The elaborate headdress competition has been going on for more than three decades with first prize now up to $3,000. This year's location is at the Truman waterfront at Southard Street. The event benefits the Key West Business Guild and is an official party of the Fantasy Fest celebration. Buy tickets in advance because event sells out.