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

Full Circle: Suzy Shuster ’90 Returns to Campus as 2025 Commencement Speaker

On June 10, 2025, Suzy Shuster, an Emmy Award–winning sports journalist and distinguished member of Winsor’s Class of 1990, will return to campus to deliver the keynote address at Winsor’s 2025 commencement ceremony.  Shuster is a nationally recognized broadcaster known for her work on ABC Sports, ESPN, and FOX Sports Net. She currently co-hosts and…

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9 students stand shoulder to shoulder on stage

2025 Annual Brooks Poetry Prize Competition

The Brooks Poetry Prize competition is a storied Winsor tradition dating back to 1909 that puts students’ public speaking skills front and center. Nine students stepped on stage in the David E. and Stacey L. Goel Theater as the final round of the competition got underway. English Department Head Courtney Jackson introduced the annual event,…

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Six female-presenting students seated on stage

Seniors Present 2025 Hemenway Speeches

Six seniors sat on the stage of the David E. and Stacey L. Goel Theater prepared to give the speech of a lifetime during all-school assembly on Thursday.  The 112th Annual Hemenway Prize for Speaking Competition has been underway for weeks. In March, the entire senior class came together in the theater and listened intently…

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