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
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays
Thursday, December 10, 2026, at 8 p.m. Celebrate the season with Shaun Cassidy as he brings his new holiday show, UNWRAPPED: Songs & Stories For The...
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Key West
Personal Effects at Fringe Theater
Dec 9 - Dec 13, 2025 Experience the world premiere of Personal Effects by local playwright Chris Moore, running December 9–13. When the adult children...
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Key West
Holiday Concert & Bazaar
Friday, December 11, 2026, from 5 to 8 p.m. Celebrate the season during the Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at...
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Key West
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Saturday, December 12, 2026, at 8 p.m. Celebrate the music and legacy of Tom Petty when The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers...
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Key West
18th Annual A Positive Step 5K Rudolph Red Nose Run
Saturday, December 12, 2026, at 8 a.m. Pull on your most festive holiday pajamas and head to the southern end of Duval Street for the 18th Annual A...
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Key West
67th Annual Key West Home Tours
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December 29–30, 2026 | January 22–23, February 12–13 & March 12–13, 2027 1–4 p.m. | Key West Ever wandered through Key West and wondered what lies...
Key West
New Year's Eve Red Shoe Drop
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
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Key West
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band
Friday, January 1, 2027, at 8 p.m. Celebrate the music and legacy of The Allman Brothers Band when The Restless Natives bring the sound of Southern...
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Key West
For the Love of Country
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**January 5 through January 9, 2027**. Get ready to two-step your way into the new year as Red Barn favorite Christine Mild returns to Key West with...
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Key West
Ben Harrison in Concert
Tuesday, January 5, 2027, at 7 p.m., with six additional performances through April. Key West singer-songwriter, author, playwright, and storyteller...
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Key West
Blanche & Beyond – Waterfront Playhouse (Spotlight Series)
January 7-9, 2027 Blanche & Beyond at Waterfront Playhouse continues the Spotlight Series with an intimate and insightful look into the life and work...
Key West
Analogous: Old Cameras. New Work. Exhibit Opening
Celebrate the opening of Analogous: Old Cameras. New Work., a collaborative exhibition by Key West photographers Michael Marrero and Mark Hedden at...
Key West
Back in Time Fundraiser – Key ‘Wild’ West
Step into the spirit of the frontier at the Key West Art & Historical Society’s annual Back in Time fundraiser, where this year’s Key ‘Wild’ West...
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Key West
Dracula: A Comedy of Terrors
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**January 19 through February 20, 2027**. Sink your teeth into the funniest, campiest night of theater in Key West as the Red Barn Theatre presents...
Key West
The Jayhawks
**Monday, January 25, 2027.** Get ready for a legendary night of Americana at the Key West Theater! Pioneering alt-country and country-rock band The...
