Special Events

John Winthrop’s special events offer fun for children and adults, and fundraising events provide support for the scholarship fund. Annual events include the Street Fair, the Auction, and Watermelon Day.

Street Fair

The annual John Winthrop Street Fair is a fun, community event to raise money for the JWS scholarship fund. Marlborough Street is closed off from Berkeley to Clarendon while families enjoy activities, rides, and food. Typical offerings include pony rides, a moonwalk bounce, a train ride, a real fire truck to explore courtesy of the Boston Fire Department, cupcake decorating, and face painting, plus cotton candy, popcorn, and food from the grill.

Watermelon Day

Watermelon Day, a long-standing JWS tradition, is the last day of the John Winthrop school year. Children gather in the outdoor amphitheater and sing for parents, friends, and relatives. The presentation ends with plenty of watermelon for everyone.