From the Head of School Fall ’25

I am thrilled to have joined the Winsor community this fall. I am embracing my role of being new, relishing all the familiar “first times” of joining a new community. The first-day butterflies, the first time eating lunch in the dining room, the first time through annual traditions like convocation and Under the Lights…the list goes on. The best part about being new is the opportunity to listen and explore. In conversations with students, faculty, staff, parents, and alumnae, I am learning about Winsor’s remarkable history of leadership in girls’ education, the deep connections that are built on Pilgrim Road, and the world-class educational experience of the students on campus today. In a few short months, I can already see Winsor’s legacy of excellence, and the enormous possibility for the future that lives within these walls.

Learning about our students’ experience, what stands out to me is the depth of the connections forged during a student’s time at Winsor. Connections to lifelong friends. Connections to educators who serve as guides through moments of excellence and struggle. And connections to the passions and aspirations that will inspire a life of meaning and contribution. Students are engaged in transformational learning opportunities in and outside of the classroom.

Winsor students jump at the chance to learn from experts in their fields, and to learn by doing—knowing that they will learn the most by trying, failing, iterating, and trying again. They do this important work of learning hand-in-hand with the adults who are dedicated to enacting Winsor’s mission.

The community of adults at Winsor takes seriously their role in the social, emotional, and educational experience of our students. Whether faculty, staff, parents, alumnae, or contractors working around the clock on our science renovation, the adults working with our students create the foundation for Winsor students to soar. It has been easy to see from my very first days on campus that the Winsor School is educating tomorrow’s world leaders on our campus today. Our students are unafraid to ask questions and create opportunities for exploration where they haven’t previously existed. This community uses every opportunity to allow students to exercise those skills and raise their voices.

I am so grateful for the warm welcome I have received to Winsor, and for the opportunity to work together with this community to imagine the future of our great school. I look forward to experiencing many more “firsts” with all of you throughout the rest of this year.

—Meredith Legg