Community Life

Inclusion and Belonging

Every school day, more than 475 students travel to Winsor from across Greater Boston to create a neighborhood on Pilgrim Road. Our students bring their whole selves to school—including their diverse talents, family backgrounds, and racial, religious, and gender identities.

Because our teachers and staff welcome students to leave no part of who they are behind, students can be themselves. They find acceptance, pass it on to their neighbors, and a community in which everyone feels like they belong.

Cultivating Connections

Students thrive in a supportive environment. We work to make everyone in our community feel valued and accepted.

Winsor Builds Community

Community News

Volleyball athletes hold a banner

Volleyball Wins It All, Securing Winsor’s First Volleyball Championship

The 2024–25 varsity volleyball team had an incredible season, finishing with an EIL league record of 11–2 and winning Winsor’s first Eastern Independent League (EIL) in-season championship. Director of Athletics Sherren Granese was nostalgic at the Fall 2024 Athletics Banquet. To a group of coaches, Upper School student athletes, and parents, Coach Granese recounted how…

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Student-athlete holds a field hockey stick and passes a ball

Fall 2024 Athletics Banquet and Season Recap

At the Fall 2024 Athletics Banquet, Upper School athletes and their families gathered in the Carolyn McClintock Peter Hall dining room for a light dinner and a special night honoring the cross country, field hockey, rowing, soccer, and volleyball teams.  “I never had to reschedule a game or even cancel a practice due to rain!”…

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2024–25 Convocation Lays the Groundwork for a Perfect Year

To mark the beginning of the 138th school year, seniors made their grand entrance into the David E. and Stacey L. Goel Theater to the Mission Impossible soundtrack (more on the senior theme below). The annual all-school convocation places faculty and staff on stage as the assembled students in Class I through Class VIII hear…

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