Join the community celebration at BayFest, the Anna Maria Island Chamber of Commerce’s signature annual street festival held on Pine Avenue in the City of Anna Maria. This free outdoor event typically runs on a Saturday in mid-October from 10 a.m. to 9 p.m., closing the avenue for a full day of island fun.
Expect live music on stage throughout the afternoon and evening, local food vendors and trucks serving a variety of bites, arts and crafts shopping, classic car displays (when featured), beer and wine options, and a welcoming community atmosphere. The 25th annual edition in 2026 drew crowds despite the weather, highlighting the event’s enduring popularity as a fundraiser and island tradition. Exact dates, lineups, vendors, and details vary each year and are subject to change.
For the latest updates on BayFest and other Chamber events, click here.
Make your visit to Anna Maria Island even more memorable by arriving by water or extending the day with a private charter. SeaEO Luxury Boat Charters offers customizable private luxury boat experiences from nearby Holmes Beach, perfect for groups of up to 13 guests seeking personalized cruising, sandbar stops, sunset views, or relaxed exploration around the island and Gulf waters.