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
Erin Cantos Wins the Pennypacker Prize
The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of…
Class I Play Celebrates the Magic of Creativity
The Winsor community was treated to a fable of childhood wonder on Friday, January 16, with the Class I play, The Magic Paintbrush. This year’s production, written specifically for Winsor’s Class of ’33 by Theater Director Jeremy Johnson, was an original musical adaptation of the Chinese folktale of the same name, with original music by…
How One Alum Is Reimagining Life in Space
First taking the stage at an all-school assembly and then dropping into classes like AP Physics to meet with students, emerging technologies designer Sana Sharma ’10 returned to Winsor. “‘Emerging technologies designer’ is a fun way of saying I couldn’t quite choose between the sciences and the arts and have found a way to do…









