Festivals in Key West

Check out happening festivals events all around Key West, FL

Wesley House Holiday Village & Bike Ride

 Fri, 05 Dec at 05:00 pm Coffee Butler Amphitheater

31st Annual Taste of Key West

 Mon, 23 Mar at 06:00 pm Truman Waterfront, Key West, FL, United States, Florida 33040

Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY

 Sun, 09 Nov at 09:00 am Hot Tin Roof Restaurant USD 403 to 805

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 03:00 pm The Alamo Key West

Q West: Comedy Escape 2026

 Fri, 10 Apr at 02:00 pm Key West Theater USD 450 to 534

Florida Keys Seafood Festival

 Sat, 14 Feb at 04:00 pm Truman Waterfront Park

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 Fri, 21 Nov at 09:00 pm The Alamo Key West

Wheeland Brothers

 Sat, 08 Nov at 08:00 pm Key West Theater

Changes In Latitude at Key West Theater

Tue, 03 Mar at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West, Floirda

61th Annual Key West Art & Craft Festival

 Sat, 21 Feb at 10:00 am Truman Waterfront Park

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West Free

Cupid's Chase 5K Key West

 Sat, 14 Feb at 09:00 am Clarence S.Higgs Memorial Beach USD 45 to 50

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews

 Tue, 25 Nov at 08:00 pm Key West Theater

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey

 Sat, 14 Feb at 08:00 pm Key West Theatre

Phil Collins Experience at Key West Theater

Mon, 26 Jan at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Key West 250th Celebration and Time Capsule Opening 2072

 Wed, 25 Mar at 09:15 am Mallory Square Key West

Crooks Second Line Parade

 Sun, 15 Feb at 12:00 pm 111 Olivia St (temporary during construction), Key West, FL

The Massacoustics at Key West Theater

 Wed, 04 Feb at 08:00 pm Key West Theater

Southernmost Turkey Trot 5K

 Thu, 27 Nov at 08:00 am The Southernmost Point Buoy

WOOF Week 2026!

 Tue, 21 Apr at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Key West Audio Tour: Hemingway’s Haunts and Island Legends

 Sat, 25 Oct at 12:00 pm Ernest Hemingway House USD 8 to 40