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

Weekly student-led assemblies bring the Lower School and Upper School together for celebrations of culture, explorations of pressing issues and current events, and showcases of theater and dance. Spirit-filled traditions like all-school assembly, Spirit Week, and the singing of “Lift Every Voice” at graduation connect Winsor’s past to the present and seal bonds of friendship and sisterhood for life.

We unite around shared interests and identities

Affinity groups build relationships among students who share a common experience. Student clubs of all kinds bring students together to explore shared interests, hobbies, and co-curricular pursuits.

We connect with our city

Winsor is a learning hub in the heart of Boston, accessible by T and within reach of centers for the arts, community-based service organizations, and the internationally renowned medical and academic institutions headquartered in the Longwood neighborhood.

Learn about how students engage with Boston.

We invest in the long term work of diversity, equity, and inclusion

We want students to explore who they are, how to be more themselves, and how to relate to others. This kind of learning happens at Winsor because prioritize it through positions like the Bezan Chair of Community and Inclusion, a fully funded faculty position, works with students, teachers, and staff to weave issues of equity and social justice into community life. Doing this work makes Winsor a more welcoming and inclusive place for everyone to be.

Read about Diversity, Equity, and Inclusion at Winsor.

Community News

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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Three students sing and hold microphones

Annual Fall Concert Showcases Six Winsor Courses

Emcees Aarna Sundaram ’29 and Rosalind Yeh ’30 welcomed the whole school to the annual fall concert on Friday, October 10, which was held in the David E. and Stacey L. Goel theater. Barely a month into the school year, students from six different performing arts courses performed for the community exploring all that they’ve…

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