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.

Learn how we build community

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

We connect with our city

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.

View upcoming community events

Community News

a group of field hockey players on the sideline at night

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…

students and a teacher seated around a conference table, facing a television with others on the screen for a remote discussion

Local Author Sparks Rich Classroom Discussion

Local Puerto Rican–Bostonian author Elizabeth Santiago visited campus last week for a conversation with two sections of AP Spanish, a course for which students had spent the summer reading her debut novel Claro de Luna. The book, which explores colonial history, Taíno identity, gentrification, and the power of community, became the foundation for a wide-ranging…