Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
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Key West
Fantasy Fest
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Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. The multi-day festival was...
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Key West
SOMO Half Marathon & 10K
Sunday, October 11, 2026. Lace up for an island run or lend a hand behind the scenes during the SOMO Marathon, Half Marathon & 10K, a Key West race...
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Islamorada
Florida Keys Farmers Market
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Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada. Held every Sunday from 10 a.m. to 3 p.m. in the parking...
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Key Largo
REEF Fest (2026)
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Dive into a weekend of underwater adventure, education, and conservation at REEF Fest, a celebration of the ocean and the spectacular marine...
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Key West
Monday Night Jazz Jams
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Kick off the week with the smooth sounds of Monday Night Jazz Jams at the William Weech American Legion Post 168 in Key West. Held every Monday from 8...
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Key West
National Dessert Day at Key West Cooking Show
October 14, 2026. Celebrate National Dessert Day with a distinctly Key West twist at the Key West Cooking Show, where one of the Florida Keys’ most...
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Key West
Womankind Greene Street Fundraiser
Join the Key West community on October 14 for a special Greene Street fundraiser benefiting Womankind, a nonprofit health center providing healthcare...
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Key West
Hedwig and the Angry Inch at Waterfront Playhouse
October 15-23, 2026 Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience presented...
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Key West
Fly Into Fantasy Fest with Tropic Ocean Airways
October 15, 16, 18, 22, 23 and 25, 2026. Skip the Overseas Highway and take to the skies during Fantasy Fest with Tropic Ocean Airways’ nonstop...
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Key Largo
REEF Fest
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Dive into four days of marine discovery, adventure, and conservation when REEF Fest returns to Key Largo October 15–18, 2026. Hosted by the Reef...
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Islamorada
Morada Way Third Thursday Art Walk
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Every third Thursday of the month from 6 to 9 p.m., Morada Way in Islamorada comes alive with color, music, flavor, and island charm. Stroll through...
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Islamorada
Guided Walks Through a Hardwood Hammock at Green Turtle Hammock
Friday, October 16, 2026, with two guided walks offered that morning. Discover the natural side of Islamorada during a guided exploration of the Green...
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Islamorada
Casting for Cats Backcountry Tournament
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October 16–17, 2026 | Islamorada Cast a line for a great cause at the annual Casting for Cats Backcountry Fishing Tournament, a longtime Upper Keys...
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Islamorada
Ladies, Let's Go Fishing! Keys Saltwater Weekend
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October 16–18, 2026. Discover the excitement of sportfishing in a fun, supportive environment during the Ladies, Let’s Go Fishing! Keys University and...
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Marathon
Witches in the Hammock
Saturday, October 17, 2026, from 6:30 to 9 p.m. Celebrate spooky season with the whole family during Witches in the Hammock at Crane Point Museum &...
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Islamorada
Islamorada Witches Paddle & Halloween Costume Swap
Saturday, October 17, 2026 from 11:00 AM to 2:00 PM. Witches, warlocks and families, let's paddle. Wear your witchiest attire and join the Islamorada...
