
October 16, 2026 - October 17, 2026
Free
Outdoor
Pet-Friendly
Food & Drink
Anna Maria Island Bayfest
Fall street festival on Pine Avenue with music, food, and a classic car show.
Event Details
Bayfest is Anna Maria Island's signature fall street festival, held each October along historic Pine Avenue in the city of Anna Maria. The event closes the avenue to traffic and fills it with live bands, food and drink vendors, a classic car show, kids activities, and local artisans. Bayfest has a warm, small town feel and is one of the most anticipated community gatherings of the year on the island's north end. Admission to the street festival is generally free, with food and drink available for purchase. Pine Avenue's shops, cafes, and galleries stay open during the celebration, making it easy to combine shopping with the festivities. From The Sandbox Beach House in Holmes Beach, the north end and Pine Avenue are a short trolley ride or drive away, so you can enjoy the evening music and still return to a quiet, pet friendly home base.
πPine Avenue
Anna Maria, FL
Plan Your Visit
Stay at Sandbox Beach House and enjoy easy access to all Anna Maria Island events. Our Holmes Beach location keeps you close to the action while providing a quiet retreat with a heated pool.
Book your stay for this event
Check availability around October 16, 2026 - October 17, 2026 and secure your spot at Sandbox Beach House. Small dogs (35 lbs or less) welcome.
