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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Featured
Islamorada
34th Annual Florida Keys Island Fest
Mar 28 - 29, 2026
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
Marathon
City of Marathon Food Truck Jamboree - Back for Seconds
Feb 25, 2026
Come out for second helpings at the City of Marathon’s Food Truck Jamboree — Back for Seconds! Bigger and better than the first event, the February...
Key West
Pet Portraits with Maggie Ruley
Feb 25 - 26, 2026
Join local artist Maggie Ruley for a creative and engaging pet portrait workshop celebrating your beloved companions. During this guided session...
Key West
RAMS HEAD PRESENTS: DMTB: THE DAVE MATTHEWS TRIBUTE BAND
Feb 25, 2026
DMTB is a celebration of the music of the Dave Matthews Band - a time machine to a funky tea party in the 90’s, a boisterous era of tape trading, sing...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Dave Edmisten at Key West Theater
Feb 25 - 26, 2026
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Featured
Marathon
Little Shop of Horrors at Marathon Community Theater
Feb 26, 2026, Feb 27, 2026, Feb 28, 2026, Mar 5, 2026, Mar 6, 2026, Mar 7, 2026, Mar 12, 2026, Mar 13, 2026, Mar 14, 2026, Mar 19, 2026, Mar 20, 2026, Mar 21, 2026
FEBRUARY 26, 27, 28 @ 8:00PM MARCH 5, 6, 7 @ 8:00PM MARCH 8 @ 3:00 PM- SUNDAY MATINEE MARCH 12, 13, 14 @ 8:00PM MARCH 15 @ 3:00PM - SUNDAY MATINEE...
Key Largo
CONNECTIONS PROJECT Pop-Up, Key Largo Chamber After Hours at REEF Center
Feb 26, 2026
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
Marathon
CONNECTIONS PROJECT Pop-Up at Art Studio by Sandra Lee
Feb 26, 2026
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
Key West
Distinguished Speaker Series: Flavor of the Peninsula | The History and Cultural Significance of Food in Florida
Feb 26, 2026
Join the Distinguished Speaker Series: Flavor of the Peninsula — a lively lecture with Dr. Cori Convertito exploring Florida’s culinary history from...
Key West
Move Like the Ocean: Build a Kinetic Cardboard Sea Creature
Feb 27, 2026
Dive into a fun, hands-on creative workshop with artist Cricket Desmarais, where participants will design and build their own kinetic cardboard sea...
Marathon
Sombrero Beach Run
Feb 27 - Mar 1, 2026
Join us in the Florida Keys for the Sombrero Beach Run! Enjoy a scenic race along beautiful Sombrero Beach, with options for all fitness levels...
Key West
Neil Berg’s 50 Years of Rock n’ Roll, Part 6 at Tennessee Williams Theater
Feb 27, 2026
With a cast consisting of both stars from Broadway's greatest rock musicals, as well as incredible Rock & Roll singers, Neil Berg shares the often...
Key West
FOOD: Celebrating Conch Cuisine
Feb 27, 2026 - Jan 3, 2027
Feb 27, 2026 - Jan 3, 2027 A landmark exhibition, FOOD: Celebrating Conch Cuisine builds on the foundation of the Smithsonian's acclaimed Food History...
Key West
FOOD: Celebrating Conch Cuisine - Exhibit Opening
Feb 27, 2026
Exhibit Runs February 27, 2026 - January 3, 2027 FOOD: Celebrating Conch Cuisine Building on the foundation of the original Smithsonian Food History...
Key West
Colin Quinn at Key West Theater
Feb 27, 2026
Catch Colin Quinn live at the historic Key West Theater on Feb 27, 2026. The Brooklyn-born comedian brings sharp, irreverent stand-up and decades of...
