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
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…
Celebrating the Class of 2025
“It is a pleasure to welcome you all here to the 131st commencement ceremony of The Winsor School,” said Head of School Sarah Pelmas. The entire student body of grades 5 through 12, faculty and staff, and family and friends of the graduating seniors gathered in a soaring white tent in the Winsor courtyard. The…
2025 Awards Celebration
Gathering in the David E. and Stacey L. Goel Theater, the Winsor community came together for the 2024–25 Awards Celebration in which Upper School and Lower School students are recognized for achievements in athletics, academics, community, and leadership. The awards celebration is a day the whole community looks forward to. While parents and guardians of…









