Key West Festivals Events

Key West Oyster Fest 2026: A Benefit for the Oyster

231 Margaret St, Key West, FL, United States, Florida 33040 14 Nov 2026

Gold Pool Parties

1129 Fleming St, Key West, FL, United States, Florida 33040 20 Sep 2026

Sunday Recognition Brunch - Key West Oyster Fest 2026

Half Shell Raw Bar 15 Nov 2026

The Lighting of the "Harbor Walk of Lights"

Conch Republic Seafood Company 25 Nov 2026

Wine Festival

Wellen Park Florida 14 Nov 2026

The 72-Hour Film Challenge: Screening Night at Williams Hall

729 Fleming Street, Key West, FL, United States, Florida 33040 17 Nov 2026

Winterfest

Sigsbee Community Center 3 Dec 2026

Trivia Night

1319 Duval Street, Key West, FL, United States, Florida 33040 4 Nov 2026

Annual Key West Food and Wine Festival

Key West 26 Jan 2027

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 12 Dec 2026

Florida Keys Seafood Festival

Truman Waterfront Park 12 Feb 2027

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band

Key West Theater 1 Jan 2027

Put-in-Bay Days in Key West 2027

Key West, Florida 10 Feb 2027

2027 Cupid's Chase 5K Key West

Higgs Beach Pavilion, 1000 Atlantic Boulevard, Key West, FL US 33040 13 Feb 2027

Key West Songwriters Getaways!®

Duval Street 27 Apr 2027

Pete Yorn Solo Acoustic: 25th Anniversary of musicforthemorningafter

Key West Theater 6 Feb 2027

Wienerpalooza 2027!

U.S. Customs House Museum 10 Jan 2027

Key West Songwriters Festival

Southernmost Beach Resort 28 Apr 2027