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.
See Some Shenanigans
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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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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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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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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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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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Islamorada
Treasure Treat Night
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Islamorada
8th Annual Trunk or Treat Halloween Party
Saturday, October 24, 2026, from 6:00 to 8:30 p.m. The Village of Islamorada throws its 8th Annual Trunk or Treat Halloween Party on the Great Lawn at...
Islamorada
Brothers of Others: Happy Halloween at Lorelei
Saturday, October 31, 2026, from 5:00 to 9:00 p.m. Brothers of Others play Halloween night at the Lorelei Restaurant & Cabana Bar, bayside at Mile...
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Islamorada
Dia De Los Muertos Celebration
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Celebrate Dia de los Muertos with memory, music and dance during a celebration in the colorful Florida Keys Brewing Company beer garden in Islamorada...
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Islamorada
Forward-Facing Sonar in Florida Bay
Friday, November 6, 2026, from 5:30 to 8 p.m. Join anglers, fishing guides, scientists, conservation professionals, and community members for an...
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Islamorada
Sip Into Fall Wine Show & Tasting
Tuesday, November 10, 2026 from 6:30 to 8:30 PM. Great wine, good company, fall vibes. City Hall Cafe and Wine Bar hosts its Sip Into Fall Wine Show &...
