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
Weekly student-led assemblies bring the Lower School and Upper School together for celebrations of culture, explorations of pressing issues and current events, and showcases of theater and dance. Spirit-filled traditions like all-school assembly, Spirit Week, and the singing of “Lift Every Voice” at graduation connect Winsor’s past to the present and seal bonds of friendship and sisterhood for life.
Affinity groups build relationships among students who share a common experience. Student clubs of all kinds bring students together to explore shared interests, hobbies, and co-curricular pursuits.
Winsor is a learning hub in the heart of Boston, accessible by T and within reach of centers for the arts, community-based service organizations, and the internationally renowned medical and academic institutions headquartered in the Longwood neighborhood.
We want students to explore who they are, how to be more themselves, and how to relate to others. This kind of learning happens at Winsor because prioritize it through positions like the Bezan Chair of Community and Inclusion, a fully funded faculty position, works with students, teachers, and staff to weave issues of equity and social justice into community life. Doing this work makes Winsor a more welcoming and inclusive place for everyone to be.
Community News
Marian Smashes the Patriarchy
Thursday, November 9, 2023—Theater Director and Performing Arts Faculty Jeremy Johnson was a little nervous when he approached Head of School Sarah Pelmas about Marian, or the True Tale of Robin Hood. After all, the play continues to be banned in some high schools across the country for its gender-bending take on the classic tale….
Cross Country Wins 19th EIL Championship Title
Friday, November 5, 2023—Winsor cross country earned their 19th Eastern Independent League Championship at Great Brook Farm over the weekend. The team finished first with a score of 68 points, beating second place Portsmouth Abbey by 14 points. Longtime coach Moriah Musto praised the athletes’ efforts calling the meet “a master class in defending their…
Winsor Races in 58th Head of the Charles Regatta
Over 100 Winsor fans stopped by the Winsor Belmont Hill Boat House for the 2023 Head of the Charles Regatta. Winsor Crew alums returned to the dock to see teammates and watch the races while current Winsor families turned out en masse to support the team. “The excitement was palpable and the Winsor fans were…









