The Headdress Ball at Fantasy Fest, Key West, Florida

Key West’s ten-day celebration Fantasy Fest that spans October 19–28  [] presents the opportunity to enjoy the fall season poolside instead of inside. The festival was founded in 1979 by the Key West Business Guild, one of the United States’ oldest LGBTQ business organizations and, from there, has grown into Florida’s premier costume extravaganza, showcasing local businesses, restaurants, and bars during the two weekends leading up to Halloween.

Second Place Time Loop Virginia Wark, Key West

Second Place Time Loop Virginia Wark, Key West

If you’re looking for good costumed fun during the festival, then look no further than the annual Headdress Ball. The event celebrates its 36th year as part of the festival, combining a variety of entertainment and creative rivalry, and promises to dazzle audiences with contestants’ flamboyant and outrageous regalia.

More than 25 entrants will don headgear, ­many with feathers, sequins, unique accessories, and even moving parts, all competing for a $3,000 prize.

Keep reading over at Passport magazine online…

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