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

Students ring a bell on stage.

Convocation Kicks Off a Fairytale Year

On Tuesday morning, “I got the magic in me” blared through the sound system of the David E. and Stacey L. Goel Theater. To mark the beginning of the 140th school year, seniors made their grand entrance to “Magic” by B.o.B featuring Rivers Cuomo (more on the senior theme below). The annual all-school convocation places…

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Celebrating the Class of 2025

“It is a pleasure to welcome you all here to the 131st commencement ceremony of The Winsor School,” said Head of School Sarah Pelmas. The entire student body of grades 5 through 12, faculty and staff, and family and friends of the graduating seniors gathered in a soaring white tent in the Winsor courtyard. The…

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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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