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

People socializing outside in a grassy courtyard standing and seated at tables

Parents’ Association Breakfast Honors Volunteers and Head of School Sarah Pelmas

The annual Parents’ Association (PA) thank you breakfast brought parents and guardians across all classes to campus. Guests noshed on a buffet of bagels and pastries while socializing and reminiscing to close out the school year.  Winsor PA Co-Chairs Aida Arain Alam P’27, ’30 and Fawn Andersen P’29 welcomed guests to the event, which also…

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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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