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

Community News

Four students on stage dressed in Renaissance costumes.

94th Annual Class IV Shakespeare Production

Opening with roiling seas and flashes of lightning, the Class of 2029 presented four performances of Twelfth Night. This year’s production took two forms, with one show set in the Renaissance and the other in 1980s Miami Beach. A Class IV tradition, the shows mark the 94th annual Shakespeare production at Winsor.  The Winsor community…

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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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