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

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
Five female athletes standing in a gym.

Six Winsor Athletes Pursue Collegiate Athletics

Winsor is thrilled to have six accomplished athletes from the Class of 2025 who are continuing their athletic careers by pursuing sports at the collegiate level.  “We are so proud of these six athletes and all they have accomplished. We have loved watching them grow as both athletes and leaders during their time at Winsor,”…

Read More about this story
Students ring a bell on stage.

Convocation Kicks Off a Fairytale Year

On Tuesday morning, “I got the magic in me” blared through the sound system of the David E. and Stacey L. Goel Theater. To mark the beginning of the 140th school year, seniors made their grand entrance to “Magic” by B.o.B featuring Rivers Cuomo (more on the senior theme below). The annual all-school convocation places…

Read More about this story