Fantasy Fest 5K Run/Walk
When: October 19, 2026 6:00 PM
Where: 201 Duvall St, Key West, FL 33040
Run Wild in Paradise: The Fantasy Fest 5K is the Most Magical Mile You'll Ever Take
Ready to lace up for the wildest Monday night of your life? Welcome to the Fantasy Fest 5K Run/Walk—where fairy tales meet finish lines and the streets of Key West come alive with whimsy, costumes, and cocktails. More than just a race, this Monday night party kicks off Fantasy Fest 2025 in true Key West style. Starting at the vibrant Tiki House on Duval Street, runners and walkers dash (or stroll) down the iconic strip dressed as magical monsters or bedtime story characters. Cross the finish and you’ll snag a whimsical medal, a free themed drink or soft drink, plus the legendary Hostess Twinkie Cake at the post-race bash back at Tiki House. Not feeling the full 5K? No sweat—literally. The Tipsy Fairy Mile offers all the swag and celebration with just a short jaunt. Whether you're in it for the fitness, the fantasy, or the festive drinks, this event is a must-visit for travelers who crave quirky fun, island energy, and unforgettable memories. So pack your wings, your wand, or your running shoes—Key West is calling, and it’s pure magic!
To Register- https://runsignup.com/Race/FL/
You might like these Events
Fantasy Fest® 2026
Key West Fantasy Fest 2026: The Ultimate 10-Day Caribbean Celebration Fantasy Fest returns to Key West for an extraordinary celebration from October 16-25, 2026, transforming the island paradise into a vibrant playground of creativity and imagination. This world-renowned festival, celebrating its legacy since 1979, invites adults from around the globe to experience ten unforgettable days of costu...
Offshore Powerboat Racing World Championships
Key West Boat Races Extravaganza The Key West Offshore Powerboat Racing World Championship is set to electrify the scene from November 1 – November 8, 2026 in Key West, FL. The event launches with a visual spectacle as the Parade Participants Lineup gathers on Sunday, November 1nd at 3:30 PM, followed by the First State Bank World's Fastest Boat Parade at 4:00 PM along Duval Street. This dynamic ...
32nd Annual 5k Hog Trot
The Hog Trot 5K returns to Key West on November 28, 2026, celebrating its 32nd anniversary with a fun mix of fitness, community, and post-race revelry. The run kicks off at 8:00 AM from Hog’s Breath Saloon, 400 Front Street, with participants enjoying perks like a free Mich Ultra and a lively post-race party featuring Grey Goose Bloody Marys, Bombora Hog A-Laides, and High Noons at discounted pric...