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

Image related to the post titled: Sara Macaulay Celebrates 40 Years at Winsor

Sara Macaulay Celebrates 40 Years at Winsor

Each winter, the Winsor Board of Trustees hosts a seated dinner for the faculty and staff to celebrate major milestones and to honor their Winsor tenure. At the annual Faculty, Staff, and Trustee Dinner on Tuesday, December 5, 2023, Visual Arts Department Head and Eleanor Thomas Nelson ’49 Chair in Fine Arts Sara Macaulay celebrated…

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Image related to the post titled: The Annual Winter Concert: Arise O Light

The Annual Winter Concert: Arise O Light

Sunday, December 10, 2023—During the darkest time of the year, the annual Winter Concert shined bright. With references to fireworks, candles, stars, and even the sun, this year’s concert theme “Arise, O Light” offered a fresh take on a concert that has traditionally been holiday-focused. An abridged concert for students, faculty, and staff on Thursday,…

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Image related to the post titled: Samantha Simpson Awarded Pennypacker Prize

Samantha Simpson Awarded Pennypacker Prize

The Pennypacker Prize is a special way for us to recognize a Winsor teacher of great promise. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” Henriette attended Wheelock…

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