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
Winsor Sailing Wins the Mass Bay Championship for the Second Year in a Row
May 22–23, 2024—Congratulations to the Winsor varsity sailing team on winning the Mass Bay C Division League Championship, which was held at Community Boating on the Charles River. The sailing team had another magnificent season, finishing number one in their division of the Massachusetts Bay League for the second year in a row. The 2024…
Spring 2023–24 Athletics Banquet and Season Recap
May 22, 2024—The seniors “wanted to go out on top and knew that to do that they had to work hard, and get everyone to believe that being a team, working together, and having fun would produce the best results,” shared Director of Athletics Sherren Granese at the Spring 2023–24 Athletics Banquet. Celebrating the crew,…
PAB Encourages Lower School Students to Take Risks
May 24, 2024—The Performing Arts Block, colloquially called PAB at Winsor, is an opportunity for Lower School students to explore the arts in Classes I through IV. Students can choose from a variety of electives in voice, dance, and orchestra, and spend the semester honing their craft, culminating in a performance for the community. On…









