From the Head of School Fall ’26

Last year, my first priority was to learn about Winsor through the eyes of our students. I spent hours talking to students about their Winsor experience. Students shared stories of deep friendships with classmates forged. They shared the joy they feel coming to campus every day to be a part of this special community of learners. And they shared the ways that Winsor has pushed them to expand their intellectual capacities. A Class VII student told me about how inspired she is to be in a school with peers and teachers driving her forward, pushing her to “reach her best,” and a Class VI student told me about how, through her time at Winsor, she has realized a confidence in her own abilities she never expected. She spoke proudly of how she knows she has the strength and the skills to conquer any problem. 

In 1886, Mary Pickard Winsor founded her school in Boston’s Back Bay to educate girls with the idea that girls could—and should—go on to the highest levels of education. Just 14 years later, the Winsor School moved to 103 Pilgrim Road, where the school remains strong and vibrant today, continuing Miss Winsor’s legacy of empowering girls to reach for the highest goals. Throughout our history, as the world has changed and a bustling city neighborhood has risen around the campus, Winsor has remained true to the Miss Winsor’s original mission: to empower girls’ intellect. 

Like the Lamp of Learning, which serves as an enduring symbol of the pursuit of knowledge that lives at the heart of Winsor, the spark that drove Miss Winsor to start her school 140 years ago burns bright today in the students, faculty, and staff on our campus each day. Winsor graduates are connected by experiences that have endured decades—some for more than a century. Whether through the Class I play, Shakespeare Project, class rings, or painting the Class VIII homeroom, these special moments form the backbone of our students’ time at Winsor. While today’s students differ in many ways from those arriving at Miss Winsor’s school in 1886, they have an essential quality in common: they believe in themselves, and want to be challenged to strive for excellence. 

As I start my second year as head of school, I am especially grateful for the generations of faculty, staff, trustees, parents, alumnae, and benefactors who built the foundation upon which we now stand. We are at the threshold of a new chapter in Winsor’s history; together, we will continue to shape this remarkable school, steadfast in our enduring mission to empower girls to lead lives of purpose, engagement, and curiosity. 

—Meredith Legg