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
Sara Macaulay Celebrates 40 Years at Winsor
Each winter, the Winsor Board of Trustees hosts a seated dinner for the faculty and staff to celebrate major milestones and to honor their Winsor tenure. At the annual Faculty, Staff, and Trustee Dinner on Tuesday, December 5, 2023, Visual Arts Department Head and Eleanor Thomas Nelson ’49 Chair in Fine Arts Sara Macaulay celebrated…
The Annual Winter Concert: Arise O Light
Sunday, December 10, 2023—During the darkest time of the year, the annual Winter Concert shined bright. With references to fireworks, candles, stars, and even the sun, this year’s concert theme “Arise, O Light” offered a fresh take on a concert that has traditionally been holiday-focused. An abridged concert for students, faculty, and staff on Thursday,…
Samantha Simpson Awarded Pennypacker Prize
The Pennypacker Prize is a special way for us to recognize a Winsor teacher of great promise. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” Henriette attended Wheelock…









