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

Team of athletes holds their trophy.

Cross Country Wins 21st EIL Championship Title

Congratulations to the Winsor cross country team who finished first with a low score of 38 points to secure their 21st Eastern Independent League (EIL) championship.  On Friday, October 31, the team travelled to Chase Farm in Lincoln, RI where the Wheeler School hosted the championships. “Winsor entered the race as the strong favorite given…

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Five students wear red clothing and hold their arms in the air

Three Decades of Under the Lights

A beloved Winsor tradition for over three decades, Under the Lights brings current and former faculty, students, alums, and parents to campus for a Friday-night celebration of Winsor community. The gathered crowds cheered on the mid, JV, and varsity soccer, field hockey, and volleyball teams as they competed in 11 contests with area schools. Hundreds…

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Seated female doctor wearing a lab coat

Lessons from Summer Reading: Courage in Action

The Winsor community gathered this fall for an inspiring virtual conversation with Dr. Mona Hanna, author of What the Eyes Don’t See: A Story of Crisis, Resistance, and Hope in an American City. Chosen as Winsor’s 2025 summer reading selection, Dr. Mona’s memoir chronicles her courageous role in uncovering the Flint water crisis and her…

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