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

Six young women and the current head of school on stage, smiling

Seniors Present 2026 Hemenway Speeches

Traditions punctuate every season of life at Winsor, marking the rhythm of the year and the milestones that shape each student’s journey. For seniors, these traditions can feel especially meaningful as each familiar experience and gathering brings them closer to graduation and life beyond Pilgrim Road. On April 2, every member of the senior class…

The Unseen Work That Keeps Winsor Going

Winsor had some invisible help staying healthy during the past few cold and flu seasons. Well, not visible to the human eye, anyway. Thanks to Winsor’s portable ultraviolet (UV) light sanitizer, the school’s facilities and janitorial teams—led by John Crompton, director of facilities and construction—have been able to maintain exceptionally clean and healthy spaces for…

Spring Rally: A New Winsor Tradition Takes the Field

On Saturday, April 11, Winsor brought student athletes, families, and fans together for a day of clinics, competition, and school spirit for the first ever Spring Rally. Below, Associate Director of Athletics Katrina Hable shares her reflection on the new event: The day began with a clinic led by our varsity lacrosse and softball student-athletes,…