St Petersburg Fall Festivals – Fall 2025 FL Events

Chalk Festival - Sarasota, FL - Nov 8 to Nov 10, 2024
An annual festival of incredible chalk drawings

Clearwater Jazz Holiday - Clearwater, FL - Oct 17 to Oct 20, 2024
A diverse lineup of musical styles including smooth jazz, swing and more enjoyed over four days and nights.

Clearwater Super Boat and Seafood Festival - Clearwater, FL - Sep 27 to Sep 29, 2024
Last year over 180,000 people filled the beaches and shores of the 2.5 mile race course, including those on over 2500 boats, as they watched super boats race each other over the three-day festival.

Island Hopper Songwriter Fest - Fort Myers Beach, FL - Sep 20 to Sep 29, 2024
A three-part event taking part on Captiva Island, Downtown Fort Myers, and Fort Myers Beach, and featuring performers who write their own songs

The I Like it HOT! Festival - Largo, FL - Sep 14 to Sep 15, 2024
The largest gourmet spicy food show in Florida. Sample and purchase hundreds of spicy foods from around Florida.

Gulfport Geckofest - Gulfport, FL - Aug 31 to Aug 31, 2024
Come on down for two stages of live music, hundreds of vendors serving up food, arts and crafts, lots of kids activities, and street performances of all kinds. Parking is free!