The annual Fantasy Façade Contest invites Key West and Stock Island creative superstars to trick out their home or business façades and enter for a chance to win creative rock star status, along with cash prizes ranging from $100-$1000. 

This year, contestants are encouraged to riff on the 2026 “Musical Icons and Iconic Musicals” theme, channel traditional Halloween ghoulishness, or concoct a show-stopping combination of both! Deadline to enter Oct. 12; judging Oct. 19; winners announced Oct. 27.

This year’s categories are:
·       Spooktacular Showstopper (Best Overall Façade): The all-around champion of creativity and craftsmanship - $1,000.
·       Home Takes Center Stage (Best Residential Interpretation of Fantasy Fest Theme): The home that best turns this year’s theme into a  memorable visual performance - $500.
·       Business Takes Center Stage (Best Commercial Interpretation of Fantasy Fest Theme): The business façade that most brilliantly brings this year’s “Musical Icons and Iconic Musicals” theme to life - $250.
·       The Great Pumpkin (Best Traditional Halloween Theme): The façade that celebrates classic Halloween charm and nostalgia - $250.
·       Stagecraft (Most Creative Design): The façade with the most unique and imaginative concept - $200.
·       Monster Mash (Scariest Display): for the façade that truly sends shivers down your spine - $100.
·       In the Spotlight (Best Use of Lighting): The most effective illumination - $100.
·       Encore (Most Entertaining – Sound/Movement): The façade that draws the crowd in with interactive fun - $100.
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Presented in partnership with Sloan’s Haunted Key West, all participating entries will be featured on the official Fantasy Fest app map- so everyone can join in the sightseeing fun and take in the neighborhood’s best façade performances. Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. Entry form and information available at fantasyfest.com/fantasy-façade

The 2026 Fantasy Fest Pet Masquerade trots out Wednesday, Oct. 21 at the Coffee Butler Amphitheater, 21 Quay Rd., Key West. Come watch and cheer, or sign up to take the stage with your costumed critter! Doors open and registration begins at 5:00pm; pets and their people take the stage beginning at 6:30pm. Prize categories include Junior, Pet/Owner Lookalike, Most Exotic, Overall Winner/Best in Show, and Best Adaptation of the 2026 Fantasy Fest “Musical Icons and Iconic Musicals” theme. Admission is free; cost to register per category is $25.00. Food and beverages available for purchase. Presented by Florida Keys Media and Fantasy Fest, proceeds benefit the Monroe County Sheriff’s Office Animal Farm. For a full calendar of Fantasy Fest events and a downloadable mobile APP, visit http://www.fantasyfest.com.​

KEY WEST, FLA. — Fantasy Fest revelers can meet the talent behind the winning 2026 Fantasy Fest poster art — and even step into his creative world — when Miami-based artist and illustrator Brian Butler appears and creates at this year’s Official Fantasy Fest Poster Signing Party, happening from 3 to 5 p.m. Tuesday, Oct. 20, in the Lobby Tropicado at the historic La Concha Hotel, 430 Duval St, Key West, Fla.

Presented by the Florida Keys Council of the Arts, the event invites guests to meet Butler, have their official 2026 Fantasy Fest posters signed, enjoy free wine sampling courtesy of Bogle Wines, and shop for 2026 Fantasy Fest T-shirts and other festival swag. Butler will also be live painting during the event, creating a classic “photo stand-in” around this year’s theme. A selfie station presented by KeyHaw and Inflate Key West will offer another opportunity to strike a pose and capture the moment.

A prolific illustrator with deep roots in the music world, Butler is known for sketchbook-style illustrations documenting major festivals and concerts around the globe. His creative repertoire also includes large-scale murals, interactive art events and work for clients like Sony Music, Vans, SXSW, and the Miami Heat.

Butler’s 2026 Fantasy Fest poster design entry, which won him a $1000 prize, is packed with fanciful references to the festival's theme, “Musical Icons and Iconic Musicals,” weaving together nods to Prince, Madonna, Wicked, Kinky Boots, Hairspray, Fiddler on the Roof, Cats, Kiss, David Bowie, The Beatles, The Grateful Dead and The Rolling Stones. There are plenty of Key West-specific surprises, too, including Robert the Doll, a cup of Coffee Butler, a lost shaker of salt and even that famously mysterious giant sponge man.
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Fantasy Fest, Key West’s annual multi-day costuming extravaganza in paradise, runs October 16-25, 2026. Presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys, for a full calendar of events and a downloadable mobile APP, visit http://www.fantasyfest.com.

KEY WEST, FLA. — Fantasy Fest revelers can meet the talent behind the winning 2026 Fantasy Fest poster art — and even step into his creative world — when Miami-based artist and illustrator Brian Butler appears and creates at this year’s Official Fantasy Fest Poster Signing Party, happening from 3 to 5 p.m. Tuesday, Oct. 20, in the Lobby Tropicado at the historic La Concha Hotel, 430 Duval St, Key West, Fla.

Presented by the Florida Keys Council of the Arts, the event invites guests to meet Butler, have their official 2026 Fantasy Fest posters signed, enjoy free wine sampling courtesy of Bogle Wines, and shop for 2026 Fantasy Fest T-shirts and other festival swag. Butler will also be live painting during the event, creating a classic “photo stand-in” around this year’s theme. A selfie station presented by KeyHaw and Inflate Key West will offer another opportunity to strike a pose and capture the moment.

A prolific illustrator with deep roots in the music world, Butler is known for sketchbook-style illustrations documenting major festivals and concerts around the globe. His creative repertoire also includes large-scale murals, interactive art events and work for clients like Sony Music, Vans, SXSW, and the Miami Heat.

Butler’s 2026 Fantasy Fest poster design entry, which won him a $1000 prize, is packed with fanciful references to the festival's theme, “Musical Icons and Iconic Musicals,” weaving together nods to Prince, Madonna, Wicked, Kinky Boots, Hairspray, Fiddler on the Roof, Cats, Kiss, David Bowie, The Beatles, The Grateful Dead and The Rolling Stones. There are plenty of Key West-specific surprises, too, including Robert the Doll, a cup of Coffee Butler, a lost shaker of salt and even that famously mysterious giant sponge man.
​
Fantasy Fest, Key West’s annual multi-day costuming extravaganza in paradise, runs October 16-25, 2026. Presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys, for a full calendar of events and a downloadable mobile APP, visit http://www.fantasyfest.com.

Key West Fantasy Fest 2026, with its “Musical Icons and Iconic Musicals” theme, kicks off October 16, but for Deep Eddy Vodka Fantasy Fest Parade float-building groups like the one organized by Mina Valdez, Zach Matusicky, Jessie Matusicky, Kit Carson Smith, Valerie Smith, and Tim Lorber, the experience starts weeks and even months earlier. From the first light-bulbs of inspiration to the final flourishes, creating a Fantasy Fest parade float is part construction project, part creative collaboration, and part wild adventure. Members of their team recently shared insights into their vision and progress:
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Will you share what you're cooking up for 2026? 
Yes! We are creating “OzFest Key West: The Emerald Tour.” It's a mash-up. Think “Wizard of Oz” infused with “Blizzard of Ozz.” We lost Ozzy Osbourne this year, so we wanted to honor him as well as throw in some Key West flair.

Have you participated in the Fantasy Fest Parade or any other Fantasy Fest events in the past? 
Pretty much everyone here today has participated in some way in the past. Some of us have helped build floats and/or marched with groups, Mina was Duchess of Fantasy Fest 2025, and Kit owns Angelina’s Pizza on Duval Street, a traditional Fantasy Fest refueling oasis. But we all wanted to do something together, so this year is the first time for us as a group.

How many team members do you expect this year? 
We have 10 people who will be onboard our float and we're expecting about 20 to 40 for our walking crowd. In fact, we are presently recruiting Lollipop Guild Munchkins and flying monkeys. Interested characters can contact Mina at [email protected].

What did you learn from past parade experiences?
Plan. Be organized. Work as a team. Have enough juice in the generator. Bring lots of beads and don't get too drunk.

Do you have a favorite feature on your float?
Valerie: Our tornado is looking pretty sick right now, and it's not done. 
Kit: I like my big-ass chair. 
Zach: I’m conceptualizing an Emerald City.
Jessie: I’m excited to see how in the world we’re going to make it look like I’m floating in a bubble.
Mina: And I get to ride on top of a castle this year so that's going to be great. 

Do you have a plan of attack or do you lean more towards spontaneity?
We are organized, but there's also a lot of spontaneity. A lot of it has just been somebody bringing up an idea and then everybody giving their opinion on it. If it works, we kind of build on that, and if it doesn't, then we move on to the next idea. There’s some singing involved, and dancing, so there'll be rehearsals, marks to hit, and we'll have to know where to hit the marks in real time during the parade.

When did your group start getting ready for the parade?
We had our first meeting one month after Fantasy Fest last year!
What kind of music are you playing?
Rock and roll! 

Any budgeting wisdom to share? Do you have a sponsor?
We are being sponsored by Kit’s podcast, “Sit With Kit,” so we’re super excited about that. And we’re all contributing to the cost, but when it comes to an actual budget, it’s been kind of buy what you need as we go and then figure it out at the end. 

Do you have any advice for anyone thinking about entering the parade? 
Just do it. Especially if you're a local, be a part of the parade. You're never going to regret it. 
Key West Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, contests, schedule updates, and a downloadable mobile APP, visit http://www.fantasyfest.com.

​Fantasy Fest in Key West is a magical escape for costumers and revelers from around the world, but it’s the locals whose creative genius and behind-the-scenes wizardry bring the spectacle to life! Whether you prefer to imagine it, build it, stitch it, or paint it—here are three fabulous ops to step into the spotlight and add your flair to the 2026 “Musical Icons and Iconic Musicals” themed extravaganza:
 
1.    Create a Fantasy Fest Parade Float, March in Costume, or Roll with Style: The world-famous parade is open to entries large and small: phenomenal floats, magnificent marchers, kinetic creations and wheeled wonders. $20,000 in cash prizes will be awarded in categories including “Best Interpretation of Theme,” “Best in Entertainment,” “Best in Costume,” and more. Looking for just-for-locals love? Monroe County residents who sign up before Sept. 18 will have their registration fee slashed in half. Non-residents who register before Sept. 18 receive 25% off.
 
2.    Be a Fantasy Fest Ambassador: Love having front-row access to the magic and your hand in keeping the Parade on point? If yes, join the volunteer Ambassador crew, the rock-stars who help guide the parade down Duval Street and ensure that everyone has a safe and sensational time. Includes a pre-event planning meeting and an invite to join the Fantasy Fest team for their annual Ambassadors social mixer.
 
3.    Go Big with the Fantasy Facade Contest: Deck out your Key West or Stock Island home or business facade and enter the 2026 Fantasy Facade contest for a chance to win cash prizes ranging from $100-$1000. Reflect this year’s “Musical Icons and Iconic Musicals” theme, channel traditional Halloween ghoulishness, or concoct a combination of both! Entry form available Sept. 1; deadline to enter Oct. 12; judging Oct. 19; winners announced Sept. 27.
 
Links, information, and guidelines for all the above and more are available at www.FantasyFest.com/GetInvolved. Fantasy Fest is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys.

Fantasy Fest invites businesses, organizations and brands to join the 2026 “Musical Icons and Iconic Musicals” themed magic. There’s a level for everyone to get in on the dream and be seen by tens of thousands of festival-goers leading up to and through the Oct. 16-25 revelry. Sponsorships help fuel the festivals iconic events which in turn support charities, celebrate creativity, and build community.

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.

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Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For all the details e-mail [email protected]. To download the partnership form visit https://fantasyfest.com/pdf/FF2026-Partnership-Opportunities.pdf

He wrote and performs the local anthem “I’m From Key West,” and has been reeling in a following from island stages and streaming platforms for about half a decade. Now, Mike Stack will bring his supercharged energy to the front of the line as Grand Marshal of the 2026 Deep Eddy Vodka Fantasy Fest Parade, set to roll down Duval Street in Key West, FL, on Saturday, Oct. 24.

Possessing a knack for creating catchy, sing-along songs with his unique island-vibe, hip-hop and country blend sound, Stack has cultivated a devoted audience by serving up the salty spirit of life in the Conch Republic with “I’m From Key West,” and other hits like “I Want My Beer,” and “Boat Days,” turning everyday moments into sing-along anthems.

We caught up with Mike ahead of Fantasy Fest to ask a few questions:
Q: This year’s Fantasy Fest theme is “Musical Icons and Iconic Musicals.” If your life were a musical, what would it be called, and who’d play you?
A: This might be too obvious, but if my life were a musical, I’d have to call it “I’m from Key West.” I was born and raised here, and so much of what I do and the music I make comes from growing up on this island. And I’d have my buddy Arron Kutner play me. He’s been preparing for the role his whole life.

Q: What are your top three (or four, or five) annual Fantasy Fest events, and why?
A: A few of my favorites are Goombay because of the culture and food; Tutu Tuesday is just one of those nights where everybody gets after it and has a good time. The parade is always incredible… the floats, the energy, and this year I hear they’ve got a pretty cool Grand Marshal. Honestly, the people watching might be my favorite event of them all. You never know what you’re going to see during Fantasy Fest!

Q: Name three musical icons, living or dead, that you would most love to see in the crowd, cheering you on during this year’s Deep Eddy Fantasy Fest Parade.
A: Bob Marley, Toby Keith, and Mac Miller. Three completely different artists, but all three have influenced the kind of music I love and the music I make. If I saw those three standing together on Duval Street cheering me on, I’d probably have to stop the float and go hang out with them.

“With this year’s Fantasy Fest theme of ‘Musical Icons & Iconic Musicals’, we couldn’t think of a better person to lead the biggest night of Fantasy Fest,” said festival director Nadene Grossman Orr. “Mike has spent years bringing music, energy, and pure Key West spirit to performance stages, and now he’ll be bringing that same energy straight down Duval Street!”
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Fantasy Fest 2026 runs Oct. 16-25 and is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, a parade entry form, a downloadable mobile APP and other information including ways to get involved, visit http://www.fantasyfest.com.

Fantasy Fest, Key West, Florida’s annual multi-day costuming party in paradise, welcomes revelers from near and far to turn the island into a living celebration of musical spectacle during this year’s extravaganza, set for October 16-25.

The 2026 Fantasy Fest theme, “Musical Icons and Iconic Musicals” invites fantasy-makers to style themselves at the center of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic, or take center stage as the musical icon – or iconic musical character – of their dreams. The sky’s no limit for this “Swift-ly” moving and “Wicked-ly” wondrous ten-day break from the ordinary.

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: Creatively transform your home or business 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 12.

 

• Oct. 16: The Royal Coronation event to crown Fantasy Fest’s 2026 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. 16 and 17: 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. 18: That Arena Rock Show at Sunset Pier: A free admission, high-energy, time-traveling theatrical tribute to classic Rock & Roll.

 

• Oct. 19: 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. 19: A Green Parrot Beatles Tribute: Jump into your yellow submarine and disembark in the 1960’s for this dress-up dance party with Key West’s very own Beatles tribute band.

 

• Oct. 20: 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 2026 t-shirts and swag.

 

• Oct. 20: Tutu Tuesday with its annual epic dance party features lights, lasers, and multiple dynamic DJ’s spinning at four different Caroline St. district area venues. Tutu’s required!

 

• Oct. 21: LUV2GLOW PARTY – Rick’s Upstairs on Duval Street transforms into a vibrant universe of fluorescent visuals, underwater-inspired décor, and pulsating house music with immersive glowing environments, DJ’s and live performers. Come dressed or painted to glow under black-lights.

 

• Oct. 21: 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. 22: The 42nd Annual Key West Headdress Ball, presented by the Key West Business Guild at the Coffee Butler Amphitheater reveals a playlist of out-of-this-world headdresses modeled by their creators along with high-energy entertainment by some of the island’s best talent.

 

• Oct. 22: Sloppy Joe’s 47th Annual Toga Party: Live music starts early and flows late at this revelry, where fantasy-makers can don traditional Roman “drape duds” or create their own 2026 Fantasy Fest theme-inspired versions. Toga costume contest welcomes individuals or groups of 2-4.

 

• Oct. 23: 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. 23: 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. 23 and 24: The magnificent mile-long Fantasy Fest Street Fair and Costume Promenade offers revelers an extravaganza of fabulous food, lively libations, arts, crafts and costumes starting at high noon and going into the night.

 

• Oct. 24: The world famous Deep Eddy Vodka 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 “Musical Icons and Iconic Musicals” theme to life. An awesome island tradition since 1979!

 

•  Oct. 25: 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. 25: Don your fabulous feathers for “The Fat Lady Sings” Tea Dance at La Te Da on Duval Street—the final official Fantasy Fest celebration.

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• Oct 26: The 2026 Fantasy Fest theme will be announced.

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“At Fantasy Fest, you can see the spectacle and be the spectacle,” said Fantasy Fest Director Nadene Grossman Orr. “Whether you arrive as a Broadway legend, rock icon, pop superstar, or icon of your own creation, this is your invitation to step into the spotlight and let your imagination take flight.”

Fantasy Fest 2026 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.

“Musical Icons and Iconic Musicals” is the official theme for Fantasy Fest 2026 –Key West, Florida’s annual multi-day costuming extravaganza in Paradise. From October 16-25, those who embrace the magnificence of all things musical can style themselves at the center of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic… You get the idea. The sky’s the limit Lucy, during this “Wicked-ly” wondrous ten-day break from the ordinary.
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Revelers can see the spectacle and be the spectacle—with celebrations including the world-famous Fantasy Fest parade; the Captain Morgan Masquerade March (aka “Locals Parade”) and Paparazzi Row; the exuberant Goombay Festival; Royal Coronation of the 2026 Fantasy Fest King, Queen, and royal court; the dazzling Headdress Ball; kooky Key West Pet Masquerade; a mile-long Duval St. street fair; concerts, pool parties, theater productions, and much more. Fantasy Fest 2026 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.