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

Celebrating the Class of 2025

“It is a pleasure to welcome you all here to the 131st commencement ceremony of The Winsor School,” said Head of School Sarah Pelmas. The entire student body of grades 5 through 12, faculty and staff, and family and friends of the graduating seniors gathered in a soaring white tent in the Winsor courtyard. The…

Read More about this story
Speaker stands at podium on stage.

2025 Awards Celebration

Gathering in the David E. and Stacey L. Goel Theater, the Winsor community came together for the 2024–25 Awards Celebration in which Upper School and Lower School students are recognized for achievements in athletics, academics, community, and leadership. The awards celebration is a day the whole community looks forward to. While parents and guardians of…

Read More about this story
People socializing outside in a grassy courtyard standing and seated at tables

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…

Read More about this story