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

We gather for weekly assembly
We unite around shared interests and identities
We connect with our city
We invest in the long term work of diversity, equity, and inclusion

Community News

Speaker stands at podium on stage.

2025 Awards Celebration

Gathering in the David E. and Stacey L. Goel Theater, the Winsor community came together for the 2024–25 Awards Celebration in which Upper School and Lower School students are recognized for achievements in athletics, academics, community, and leadership. The awards celebration is a day the whole community looks forward to. While parents and guardians of…

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Lacrosse team poses in two lines

Spring 2024–25 Athletics Banquet 

“It was a terrible spring, weather wise, but it was a good spring on the river, fields, track, and courts!” joked Director of Athletics Sherren Granese at the Spring 2024–25 Athletics Banquet. Teams often compete on Saturdays and Ms. Granese noted it rained every Saturday from March 22 through June 7. Despite the weather, “Thank…

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Team of female athletes pose with their first place trophy.

Varsity Track and Field Wins 9th EIL Championship

The varsity track and field team won their 9th straight Eastern Independent League Championship on Saturday, May 10 at East Providence High School in Rhode Island.  Winsor finished first with a total of 148.50 points—27 points over second place finisher Concord Academy’s 121.50 and 70 points over third place finisher Portsmouth Abbey’s 78. “The weather…

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