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
Key West Farmers Market
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Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air...
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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
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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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...
Key West
Native Plant Sale at Key West Tropical Forest & Botanical Garden
Saturday, October 17, 2026, from 9:00 a.m. to 12:00 p.m. The Key West Tropical Forest & Botanical Garden holds a native plant sale, with staff on hand...
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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
The Hoy Shanty Crew Sing-Along
Saturday, October 17, 2026, from 6 to 8 p.m. Raise your voice and discover the musical traditions of life at sea during the first-ever Hoy Shanty Crew...
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Islamorada
Islamorada Witches Paddle & Halloween Costume Swap
Saturday, October 17, 2026, from 11 a.m. to 2 p.m. Witches, warlocks, and families are invited to grab a paddle and celebrate spooky season on the...
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Key West
Junk in the Trunk: Fantasy Fest Costume Swap
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Saturday, October 17, 2026, from 8 a.m. to 1 p.m. The Truman Waterfront Community Yard Sale, better known as Junk in the Trunk, returns for its fall...
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The Lower Keys
Open Air Market at Boondocks
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Every Saturday from 9 a.m. to 2 p.m., Boondocks Open-Air Market brings island flavor, local creativity, and tropical charm to Mile Marker 27.5 on...
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Islamorada
Mote Marine Laboratory Trivia Night at Florida Keys Brewing Company
Monday, October 19, 2026, from 7:30 to 9:30 p.m. Grab a drink, gather your smartest friends, and put your marine knowledge to the test during Mote...
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Marathon
Children's Tours & Concert Series at Crane Point Museum & nature Center
Select dates throughout 2027: January 11 and 25; February 8 and 22; March 22; April 8, 13, 15 and 29; May 20; June 14 and 28; July 12; August 23; and...
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Islamorada
Cortadito: A Tribute to the Buena Vista Social Club
Monday, October 19, 2026, at 6 p.m. Experience the rhythms of traditional Cuban music when Cortadito brings its tribute to the legendary Buena Vista...
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Key West
The Greatest Hits Pool Party
Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows...
