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
Community News
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…
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…
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,”…









