Key West Festivals Events
Festivals Happening Next in Key West, FL
Golf Cart Facade Viewing Tour Fantasy Fest
3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040
29 Oct 2025
SPORTS
Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY
Hot Tin Roof Restaurant
9 Nov 2025
SPORTS
USD 403 TO 805
31st Annual Taste of Key West
Truman Waterfront, Key West, FL, United States, Florida 33040
23 Mar 2026
DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th
The Alamo Key West
5 Dec 2025
MUSIC
Wesley House Holiday Village & Bike Ride
Coffee Butler Amphitheater
5 Dec 2025
CYCLING
Q West: Comedy Escape 2026
Key West Theater
10 Apr 2026
COMEDY
USD 450 TO 534
Melon Jelly LIVE @ The Alamo, Key West FL 🎶
The Alamo Key West
21 Nov 2025
PARTIES
Shoreline Sessions Reggae Beach Festival
1319 Duval Street, Key West, FL, United States, Florida 33040
1 Nov 2025
REGGAE
Freedom Flotilla Festival
Key West, Floirda
19 Dec 2025
FESTIVALS
61th Annual Key West Art & Craft Festival
Truman Waterfront Park
21 Feb 2026
ART
Freedom Flotilla Festival
Key West
19 Dec 2025
FESTIVALS
FREE
CFK Community Day 2025
5901 College Rd, Key West, FL 33040-4315, United States
1 Nov 2025
FESTIVALS
Wheeland Brothers
Key West Theater
8 Nov 2025
ENTERTAINMENT
Cupid's Chase 5K Key West
Clarence S.Higgs Memorial Beach
14 Feb 2026
SPORTS
USD 45 TO 50
Florida Keys Seafood Festival
Truman Waterfront Park
14 Feb 2026
FESTIVALS
FANTASY FEST. STREET FAIR
700 Duval St, Key West, FL 33040-7404, United States
1 Nov 2025
FESTIVALS
Changes In Latitude at Key West Theater
512 Eaton St, Key West, FL, United States, Florida 33040
3 Mar 2026
ENTERTAINMENT
The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews
Key West Theater
25 Nov 2025
MUSIC
A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey
Key West Theatre
14 Feb 2026
Phil Collins Experience at Key West Theater
512 Eaton St, Key West, FL, United States, Florida 33040
26 Jan 2026
MUSIC
Key West 250th Celebration and Time Capsule Opening 2072
Mallory Square Key West
25 Mar 2026
KIDS
2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!
Sebago Key West
31 Oct 2025
Crooks Second Line Parade
111 Olivia St (temporary during construction), Key West, FL
15 Feb 2026
PARADES
The Massacoustics at Key West Theater
Key West Theater
4 Feb 2026
CONTESTS
Southernmost Turkey Trot 5K
The Southernmost Point Buoy
27 Nov 2025
THANKSGIVING
Fantasy Fest
Key West, Florida
26 Oct 2025
FESTIVALS
WOOF Week 2026!
1129 Fleming St, Key West, FL, United States, Florida 33040
21 Apr 2026
PARTIES
Key West Audio Tour: Hemingway’s Haunts and Island Legends
Ernest Hemingway House
25 Oct 2025
ART
USD 8 TO 40
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Key West Festivals Events