Towering Artistry Rules the Night at Fantasy Fest Headdress Ball
FLORIDA KEYS VIDEO ADVISORY October 24, 2025
Contacts: Mary B. Haban, Mary@fla-keys.com (813) 210-8585 or Chad Newman, Chad@fla-keys.com (310) 283-8441
Story: Towering Artistry Rules the Night at Fantasy Fest Headdress Ball
Locator: Key West, Fla.
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Photo Captions Below
Video: B-roll of contestants unveiling their elaborate headdress creations during the Fantasy Fest Headdress Ball in Key West, Fla.
TRT: 1:25
Filename: KeyWestHeaddress.mp4
Video Source: Florida Keys News Bureau
Photos & Captions: Below
Towering Artistry Rules the Night at Fantasy Fest Headdress Ball
KEY WEST, Fla. (Oct. 24, 2025) — Outrageous headwear. Towering creations. Magnificent Masks. And larger-than-life personalities rocked center stage in Key West, Florida Thursday night.
The over-the-top evening was all part of the 42nd Annual Headdress Ball — a signature event during Fantasy Fest that challenges competitors to unleash their creative prowess with show-stopping designs...from the shoulders up! The contestants transformed Key Wests’ Coffee Butler Amphitheater into a dazzling spectacle as they competed for a five-thousand-dollar grand prize — and a coveted title.
The theme? “Bedtime Stories and Magical Monsters.” And the creations from contestants were nothing short of pure theatrical magic.
The crowd went wild as contestants brought their high-energy performances to life, with longtime host Randy Roberts at the helm. Their jaw-dropping head-dresses ranged from fantastical dream-world beasts to intricate mechanical designs. But they didn’t stop there...many contestants got decked out in full-body costumes, which added to the evening’s dramatic flair.
The elaborate event raises funds to support year-round efforts to promote Key West as destination where everyone feels welcome.
And if you’re having a case of serious FOMO, there’s still time to take in Fantasy Fest which continues through Sunday, Oct. 26, with the Captain Morgan Masquerade March on Friday and Saturday night’s wildly popular grand finale — the Deep Eddy Vodka Fantasy Fest Parade; which packs the streets and rooftops of Key West’s famed Duval Street.
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NOTE TO EDITORS/PRODUCERS
Below is the lineup of Florida Keys News Bureau video coverage for the rest of this week, with corresponding feed dates and delivery times. Separate advisories will be distributed before each feed.
Saturday, Oct. 25 — by 11 a.m. Captain Morgan Masquerade March from Friday evening, Oct. 24. This exuberant walking parade through Key West’s historic Old Town draws several thousand merrymakers wearing glittering masks, body paint, and costumes inspired by the “Bedtime Stories and Magical Monsters” theme. Revelers stop along the route at guest houses for music, photos, and refreshments.
Sunday, Oct. 26 — by 11 a.m. Deep Eddy Vodka Fantasy Fest Parade from Saturday night, Oct. 25. The festival’s grand finale features dazzling floats, marching groups, and costumed participants bringing the “Bedtime Stories and Magical Monsters” theme to life before tens of thousands of spectators along Duval and Whitehead streets. Leading the parade as 2025 Grand Marshal is Key West’s iconic red high-heeled shoe, a beloved island symbol since 1997.
Monday, Oct. 27 — by 11 a.m. Underwater Pumpkin Carving Contest in Key Largo, from Sunday, Oct. 26. Divers and snorkelers will descend beneath the surface of the Florida Keys National Marine Sanctuary to carve pumpkins underwater in a creative competition held off Key Largo. The event blends artistry with a one-of-a-kind underwater setting and is expected to attract both local participants and visiting dive enthusiasts. Coverage is weather dependent and will proceed as conditions allow.
Guy Hermelin of Key West, Fla., dazzles the crowd wearing his creation “Astraea the Magnificent Dream Dragon” during the 42nd annual Headdress Ball at the Coffee Butler Amphitheater in Key West, Fla., Thursday night, Oct. 23, 2025. Hermelin’s intricate design, crafted from coroplast, PVC, fabric and cellophane, earned him First Place honors and a $5,000 prize at the event, a highlight of Fantasy Fest 2025 themed “Bedtime Stories and Magical Monsters.” (Mark Hedden/Florida Keys News Bureau)
Virginia Wark of Key West, Fla., rocks the stage in her Beetlejuice-inspired creation “Sandworm Escape” during the 42nd annual Fantasy Fest Headdress Ball at the Coffee Butler Amphitheater in Key West, Fla. Thursday night, Oct. 23, 2025. Wark’s whimsical design, built from a MARC House plant store frame and materials recycled from previous years’ entries, earned her Second Place and a $3,000 prize at the Fantasy Fest 2025 event themed “Bedtime Stories and Magical Monsters.” (Mark Hedden/Florida Keys News Bureau)
From left, Jill Malcolm, Guy Hermelin, and Virginia Wark, all of Key West, Fla., are met with cheers after being named the top three winners at the 42nd annual Headdress Ball at the Coffee Butler Amphitheater in Key West, Thursday night, Oct. 23, 2025. Hermelin captured First Place with “Astraea the Magnificent Dream Dragon.” Wark earned Second for “Sandworm Escape.” And Malcolm took Third Place for her creation “Bookish Bride.” The event, themed “Bedtime Stories and Magical Monsters,” is part of Fantasy Fest which continues through Sunday. (Mark Hedden/Florida Keys News Bureau)
In a prelude to Halloween, Randall Lail dances in his spooky “Pumpkin Head” creation during the 42nd annual Headdress Ball at the Coffee Butler Amphitheater in Key West, Fla. Thursday night, Oct. 23, 2025. The elaborate event, themed “Bedtime Stories and Magical Monsters,” showcased imaginative entries during Fantasy Fest 2025, which continues through Monday. (Mark Hedden/Florida Keys News Bureau)