• 45th Annual Gloucester Waterfront Festival

    45th Annual Gloucester Waterfront Festival

    Stage Fort Park  

    The historic Stage Fort Park along Gloucester Harbor will blossom into color and flavor for the 45th Annual Gloucester Waterfront Festival on Saturday, August 15th and Sunday, August 16th, 2026....

    There is no entry fee for the Fair. There is a parking fee at the beach parking lot. Make online parking reservations here: https://gloucester.blinkay.app/login
  • Gloucester Block Party #3

    Main Street, Gloucester, MA 01930  

    Main Street, Downtown Gloucester comes alive when the Street is closed off and we have live music, street performers, vendors, food vendors and more! Many of our Shops and Businesses...

    Free

    Rockport Autumn Market Pop-Up

    1 Twin Light Circle, Rockport, MA 01966  

    Join us for a cozy fall afternoon at an Autumn Market Pop-Up, a small, community-style craft fair featuring local makers, handmade goods, and seasonal treats. Set in a warm backyard...