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

Three students sing and hold microphones

Annual Fall Concert Showcases Six Winsor Courses

Emcees Aarna Sundaram ’29 and Rosalind Yeh ’30 welcomed the whole school to the annual fall concert on Friday, October 10, which was held in the David E. and Stacey L. Goel theater. Barely a month into the school year, students from six different performing arts courses performed for the community exploring all that they’ve…

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Give students wear harnesses for a ropes course activity outside

Connecting Outside the Classroom

Each September, Winsor students leave the classroom behind and head off campus for class retreats. “It is really special that Winsor builds time in our schedule to have some fun as a class!” shared a Class VI student.  Creating and fostering community is a hallmark of the Winsor experience. In support of that mission, class…

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Four alums from across generations look at archival documents.

Forever Learning

During Alumnae Weekend, attendees had the option to attend one of three concurrent master classes on Saturday afternoon. Presented by Winsor staff and alumnae, each class offered a brief deep dive into a different subject, giving attendees the chance to engage in literary and historical discussions, flex their artistic muscles, and even explore Winsor’s own…

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