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
Varsity Track and Field Wins 9th EIL Championship
The varsity track and field team won their 9th straight Eastern Independent League Championship on Saturday, May 10 at East Providence High School in Rhode Island. Winsor finished first with a total of 148.50 points—27 points over second place finisher Concord Academy’s 121.50 and 70 points over third place finisher Portsmouth Abbey’s 78. “The weather…
Parents’ Association Breakfast Honors Volunteers and Head of School Sarah Pelmas
The annual Parents’ Association (PA) thank you breakfast brought parents and guardians across all classes to campus. Guests noshed on a buffet of bagels and pastries while socializing and reminiscing to close out the school year. Winsor PA Co-Chairs Aida Arain Alam P’27, ’30 and Fawn Andersen P’29 welcomed guests to the event, which also…
94th Annual Class IV Shakespeare Production
Opening with roiling seas and flashes of lightning, the Class of 2029 presented four performances of Twelfth Night. This year’s production took two forms, with one show set in the Renaissance and the other in 1980s Miami Beach. A Class IV tradition, the shows mark the 94th annual Shakespeare production at Winsor. The Winsor community…









