Dreamers, night creatures and storybook stars are invited to adorn themselves in their most inspired themed attire and immerse in 10 days and nights of stellar revelry for Key West Fantasy Fest 2025, set to run October 17-26.
​
This year’s theme, “Bedtime Stories and Magical Monsters” celebrates the full spectrum of imagination – those tales that tucked us in at night and the monsters that lurked in the dark. Here’s a sampling of just some of this year’s highlights. Complete information for events, times, locations, and contest entry links can be found at http://www.fantasyfest.com:

• Fantasy Façades Contest: Transform your home or business in to a storybook scene or monster’s lair for a chance to win cash prizes ranging from $100-$1000. Reflect this year’s theme or channel traditional Halloween ghoulishness! Entry form available Sept. 1; deadline to enter Oct 13.
• Oct. 17: The Royal Coronation event to crown Fantasy Fest’s 2025 King and Queen is a dazzling 2-hour stage show at the Coffee Butler Amphitheater that features performances by the intrepid competitors along with local celebrities. Proceeds benefit the Florida Keys SPCA.
• Oct. 17 and 18: The Bahama Village Goombay Festival is a two-day, family friendly celebration of island arts and crafts, culture, music and food held throughout Key West’s historic Bahama Village neighborhood.
• Oct. 19: The annual Zombie Bike Ride invites undead of all ages to immerse in ghoulish revelry. Zombies descend on Fort East Martello in the afternoon for fun and entertainment including body painting, refreshment vendors and a kids’ zone. Come evening, thousands of zombies on wheels take to the streets of Key West.
• Oct. 20: Sloppy Joe’s Comic Book Cape-ers Party: Suit up as your favorite caped superhero or villain, groove on the dance floor to live music, and compete in a costume contest with prizes for 1st-3rd place winners.
• Oct. 20: Mrs. Roper’s Romp: Break out your colorful caftan and signature curly red wig for a groovy “Three’s Company” inspired party at Sunset Pier filled with music, photo ops, dancing, games, and prizes.
• Oct. 21: Florida Keys Council of the Arts Fantasy Fest poster-signing party at the La Concha Hotel: Meet the artist, get your poster signed, and stock up on other collectable Fantasy Fest 2025 t-shirts and swag.
• Oct. 21: Tutu Tuesday with its annual epic dance party featuring a plethora of dynamic DJ’s happens across multiple Caroline St. district area venues. Tutu’s required!
• Oct. 22: Pet Masquerade, presented by Florida Keys Media at the Coffee Butler Amphitheater: Costume up with your favorite critter friends at this over the top competition or cheer them on from the audience. Prizes in multiple categories; registration fees benefit the Monroe County Sheriff’s Office Animal Farm.
• Oct. 23: The 42nd Annual Key West Headdress Ball, presented by the Key West Business Guild at the Coffee Butler Amphitheater reveals a dreamscape of out-of-this-world headdresses modeled by their creators along with high energy entertainment by some of the island’s best talent.
• Oct. 24: Paparazzi Row is the place to get warmed up and strut your stuff for the camera’s ahead of the Captain Morgan Masquerade March. Dance music will play and local paparazzi, photo booths and selfie stations will be set up to record epic costumed crews.
• Oct. 24: The Captain Morgan Masquerade March (aka “Local’s Parade”) brings all creative hands on deck as costumed revelers parade through Old Town Key West, stopping along the route for adult beverage samples provided by selected guest houses.
• Oct. 24: The magnificent mile-long Fantasy Fest Street Fair returns to Duval Street this year, offering revelers an extravaganza of fabulous food, lively libations, arts, crafts and costumes starting at high noon and going into the night.
• Oct. 25: The world famous Key West Fantasy Fest Parade in Old Town Key West presents a dazzling array of fabulous floats, magnificent marching groups, and cool kinetic contraptions to bring this year’s “Bedtime Stories and Magical Monsters” theme to life. An awesome island tradition since 1979!
•  Oct. 26: Children’s Day at Bayview Park offers a daytime fest from noon to 5:00pm with games, food, rides, entertainment, arts & crafts, and a costume contest for the kids.
• Oct. 26: Don your fabulous feathers for “The Fat Lady Sings” Tea Dance at La Te Da on Duval Street—the final official Fantasy Fest celebration.
• Oct 27: The 2026 Fantasy Fest theme will be announced.

‘“Bedtime Stories & Magical Monsters” invites everyone to tap into the dreams and whimsy of childhood, and yes, even the wild things that once lived under our beds,” said Fantasy Fest Director Nadene Grossman Orr. “It’s a playground for the imagination and all of us behind the Fest can’t wait to see how this year’s celebrators bring it to life.”

Fantasy Fest 2025 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, schedule updates, contest details, and a downloadable mobile APP, visit http://www.fantasyfest.com.

Fantasy Fest 2025 invites businesses, organizations and brands to join the 2025 “Bedtime Stories & Magical Monsters” themed magic and become part of the fantasy. There’s a level for everyone to get in on the dream and be seen by tens of thousands of revelers leading up to and through the Oct. 17-26 revelry.

Sign on for a customizable partnership, or select from a ready-made sponsorship menu for these perks and more:

• Revelers ($1000): Includes free Parade float entry, business listing on Fantasy Fest website and app, 2 official t-shirts and posters, 2 social media posts, and one e-newsletter ad.
• Merrymakers ($2000): Includes all Reveler perks plus use of the Fantasy Fest logo, your logo on listings, more merch, more posts, and two e-newsletter ads.
• Life of the Party ($3500): Host an official Fantasy Fest event with social media and graphics support; plus top tier digital features including a rotating banner ad and special listings in the Fantasy Fest app, plus everything listed above.
• Fantasy Visionary ($5500): Go big with all the above, but with two official events, premium website/app placement, Street Fair space, and radio spotlight love.

Your brand. Center stage. In a dreamscape of monsters and magic.
​
For all the details and to download the partnership form visit www.fantasyfest.com/pdf/FF2025-Partnership-Opportunities.pdf. Questions? E-mail [email protected]. 

“Bedtime Stories & Magical Monsters” is the official theme for Fantasy Fest 2025 –Key West, Florida’s annual multi-day costuming extravaganza in Paradise. From October 17-26, those who embrace the whimsical and the wild can costume up and step into a realm of storybook visions and otherworldly creatures —released from their hidden places under the bed.

Ten days and nights of fearless creativity include events like the world-famous Fantasy Fest parade, the all-hands-on-deck Captain Morgan Masquerade March (aka “Locals Parade”) and Paparazzi Row, the exuberant Goombay Festival in the streets, Royal Coronation of the 2025 Fantasy Fest King, Queen, and royal court, plus concerts, pool parties, theater productions, the ever-enchanting Key West Pet Masquerade, the dazzling annual Headdress Ball, a magnificent mile-long Duval St. street fair, and much more. Fantasy Fest 2025 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, visit http://www.fantasyfest.com.

The Florida Keys wildly creative cosmic character was on full display in an out-of-this-universe moving pageant Saturday night as the world famous Key West Fantasy Fest parade made its way down Duval Street, celebrating its 45th year and the 2024 theme, “It’s a 90s NEON Cosmic Carnival!”

Each year, following the parade, prizes are awarded by a panel of judges to multiple “Best Of” entries in a variety of categories, followed by announcement of the following year’s Fantasy Fest theme.

This year, nearly 50 entries competed for $20,000 in prizes, and the winners are:  

• $3000 Best in Entertainment: “Cosmic Neon Lambada—90s and Forever!” by Pamela Stephenson Connolly’s Key West International Dance Company.
• $3000 Best in Costume: “Cosmic Vortex” by Daniel Bitnar.
• $2500 Best Interpretation of Theme: “Fantasy Quest” by the Lower Keys Fluffers.
• $2000 Best Walking Group: “DJ Time Warp and the Power Ravers” by Guy Hermelin.
• $1500 The Green Parrot’s Best Live Music Award: “Space Force X” by Stan Shaw.
• $1000 Best Bicycle Award: “Cosmic Carnival” by Southernmost Slow Riders.
• $1000 Directors Choice Award: “Grand Marshal” by David Sloan.

​The $6000 Key West Fantasy Fest Parade Grand Prize for Best Overall, presented by The Lodging Association of the Florida Keys & Key West, is awarded to Jaimie Gwidt’s Key West Kreatives with their entry “Flagler’s 1890s Fantasy.”

The winning theme for Key West Fantasy Fest 2025, which is scheduled for Oct. 17-26, is “Bedtime Stories & Magical Monsters.” Ellen LaMoia of Key West, Fla., has scored Fantasy Fest Parade Grand Stand seats where she will enjoy the 2025 spectacle seated among the parade’s judges and organizers for her contribution to the theme.
“The Monroe County Tourist Development Association Board of Directors all agreed that “Bedtime Stories & Magical Monsters” elicits wonderfully enchanting and deliciously scary imaginings—from fresh twists on historic fables to new takes on mythical beasts—such as the ones that might be found hiding under beds,” said Nadene Grossman Orr, Fantasy Fest Director and President/CEO of We’ve Got the Keys.

Fantasy Fest events and happenings wrap up on Sunday with a slate of happenings, including Children’s Day at Bayview Park, a “Fantasy Pickleball Tournament” at Higgs Beach Courts, “The Fat Lady Sings” Tea Dance at La Te Da Hotel, Restaurant, Cabaret and Bars, Fest finale’ pool parties held at Island House Resort, the Southernmost Beach Resort, and a pool party/concert at The Marker. 

Fantasy Fest 2024 featured more than 100 events citywide and was presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. Visit http://www.fantasyfest.com for photo galleries of 2024 highlights and advance 2025 festival news and information.  

The Captain Morgan Masquerade March, called “The Local’s Parade” on account of being one of Key West Fantasy Fest’s most loved events among locals, is set to take place Friday, Oct. 25, in the island’s Old Town district.

It’s a moving mosaic of creativity where revelers of all ages, and a variety of species, costume up and sashay, strut, and perambulate in community through Old Town, taking and posing for photos and stopping at intervals for cocktail samples and thirst quenchers offered at select guesthouses along the route. 

This year, rather than one official starting point there will be two:

Starting Point One will be at the usual gathering place and time: 5:30pm on Frances St. in proximity to Old Town Wine & Spirits at the corner of Truman Ave. This route will follow Frances St. to Fleming St., hang left, and then head up Fleming to Duval St.

Starting Point Two is the newly hatched “Paparazzi Row,” where dance music will play and local paparazzi, photo booths and selfie stations will be set up to record epic costumed crews. The Paparazzi Row pre-party starts at 4:00pm on Fleming St. in proximity to Island House and Alexander’s Guest House and then will proceed up Fleming to Duval St.

Once at Duval St., those of legal age who want to continue the party can proceed to Captain Morgan’s Official Pirate After Party at Kaya Empourium, and Hog’s Breath Saloon’s Surf’s Up Party.
​
Fantasy Fest 2024 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For more information visit http://www.fantasyfest.com.