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

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…

Read More about this story
Two alums sit at a table having dinner in a crowded room.

A Special 5th Reunion Dinner for the Class of 2020

The Winsor Class of 2020 had an unusual final spring semester, celebrating their graduation and many other events virtually even receiving their diplomas in festive, albeit a socially distanced, event on the turf. During Winsor Alumnae Weekend 2025, the Class of 2020 finally gathered with their families for a special fifth-reunion dinner that brought some…

Read More about this story
Nine adults stand outside in front of flowering bushes

Welcome New Faculty and Staff — 2025

As we kick off the 2025–26 school year, we are excited to welcome new faculty, administrators, and staff to the Winsor community. While many folks are just beginning their Winsor tenures this academic year, some familiar faces started working on campus last spring and over the summer. Please give a warm Winsor welcome to our…

Read More about this story