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

Two women posing side by side, smiling.

Erin Cantos Wins the Pennypacker Prize

The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. 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…

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a group of student performers dancing on stage

Class I Play Celebrates the Magic of Creativity

The Winsor community was treated to a fable of childhood wonder on Friday, January 16, with the Class I play, The Magic Paintbrush. This year’s production, written specifically for Winsor’s Class of ’33 by Theater Director Jeremy Johnson, was an original musical adaptation of the Chinese folktale of the same name, with original music by…

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Sana Sharma gestures with hand at the front of a classroom

How One Alum Is Reimagining Life in Space

First taking the stage at an all-school assembly and then dropping into classes like AP Physics to meet with students, emerging technologies designer Sana Sharma ’10 returned to Winsor. “‘Emerging technologies designer’ is a fun way of saying I couldn’t quite choose between the sciences and the arts and have found a way to do…

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