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

We gather for weekly assembly

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.

We unite around shared interests and identities

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.

We connect with our city

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.

Learn about how students engage with Boston.

We invest in the long term work of diversity, equity, and inclusion

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.

Read about Diversity, Equity, and Inclusion at Winsor.

Community News

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…

Read More about this story
Speaker stands at podium on stage.

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…

Read More about this story
Lacrosse team poses in two lines

Spring 2024–25 Athletics Banquet 

“It was a terrible spring, weather wise, but it was a good spring on the river, fields, track, and courts!” joked Director of Athletics Sherren Granese at the Spring 2024–25 Athletics Banquet. Teams often compete on Saturdays and Ms. Granese noted it rained every Saturday from March 22 through June 7. Despite the weather, “Thank…

Read More about this story