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Bayfest on Anna Maria Island

Pine Avenue, Anna Maria Island, FL 34216 Pine Avenue, Anna Maria Island, FL

Get ready for a beloved island tradition! Bayfest is Anna Maria Island’s annual October street festival that celebrates the laid-back coastal lifestyle with live music, delicious food, refreshing drinks, and a lively classic car show. Stroll along Pine Avenue and browse unique arts and crafts vendors, enjoy family-friendly activities, and soak up the festive island atmosphere. This free event is a perfect way to kick off the fall season and experience the charm of Anna Maria Island like a local.

Sarasota Food Truck Festival

Sarasota Food Truck Rally & Music Festival

The Sarasota Food Truck Rally & Music Festival is a vibrant three-day celebration held annually over Thanksgiving weekend. Set against the scenic backdrop of Sarasota Bay at J.D. Hamel Park, the festival features a diverse lineup of food trucks offering a wide array of culinary delights, from gourmet dishes to classic comfort foods. Attendees can enjoy live music performances spanning various genres, creating a lively and entertaining atmosphere for all ages. The event is pet-friendly, with leashed pets welcome, and offers free admission to all visitors. ​