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
Community News
Full Circle: Suzy Shuster ’90 Returns to Campus as 2025 Commencement Speaker
On June 10, 2025, Suzy Shuster, an Emmy Award–winning sports journalist and distinguished member of Winsor’s Class of 1990, will return to campus to deliver the keynote address at Winsor’s 2025 commencement ceremony. Shuster is a nationally recognized broadcaster known for her work on ABC Sports, ESPN, and FOX Sports Net. She currently co-hosts and…
2025 Annual Brooks Poetry Prize Competition
The Brooks Poetry Prize competition is a storied Winsor tradition dating back to 1909 that puts students’ public speaking skills front and center. Nine students stepped on stage in the David E. and Stacey L. Goel Theater as the final round of the competition got underway. English Department Head Courtney Jackson introduced the annual event,…
Seniors Present 2025 Hemenway Speeches
Six seniors sat on the stage of the David E. and Stacey L. Goel Theater prepared to give the speech of a lifetime during all-school assembly on Thursday. The 112th Annual Hemenway Prize for Speaking Competition has been underway for weeks. In March, the entire senior class came together in the theater and listened intently…









