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.
“I introduce culinary techniques and flavors to young minds at Winsor, turning the cafeteria into its own classroom and celebrating cultures and heritages that represent the community.”
Culinary Director
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
Gevvie Stone ’03 Receives NEPSAC Martin William Souders Memorial Award
Last month, during the annual meeting of the New England Preparatory School Athletic Council (NEPSAC), Olympian rower and physician Dr. Gevvie Stone ’03 received the organization’s Martin William Souders Memorial Award. The award is presented each year to a New England Independent School graduate with a distinguished athletic record who has gone on to distinction…
2025 Fall Athletics Banquet and Season Recap
With the latest season wrapped, varsity and JV athletes, families, and coaches gathered to honor the crew, cross country, field hockey, soccer, and volleyball teams at the 2025 Fall Athletics Banquet. Held in the dining room in Carolyn McClintock Peter Hall, the event drew a substantial crowd. Addressing the room, Director of Athletics Sherren Granese…
Thankful for Grandparents and Grandfriends
Eager older learners streamed into the Wildcat Room ready to start their school day at Winsor’s annual Grandparents’ and Grandfriends’ Day event. The special program brought more than 160 visitors to campus the day before Thanksgiving break. While the whole school enjoyed a festive morning snack of cinnamon sugar donuts, students with grandparent and grandfriend…