Celebrate the end of summer at Tivoli Day—Oak Bluffs’ beloved street festival—on Saturday, September 20, 2025, from 10 AM–6 PM (rain date Sunday).
Stroll Circuit Avenue, enjoy live music, art, family fun, and tasty island treats, plus don’t miss the thrilling Ring Challenge on the Flying Horses carousel. Free entry. Bring your appetite, cash, and fall spirit—let’s send off summer in style!