Head of the Upper School

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston’s Longwood Medical and Academic Research area, our students benefit from the school's longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and diverse and talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious and socio-economic diversity among all the constituencies of the school.

Winsor supports this commitment through its inclusive curriculum, success addressing a range of learning styles, availability of a wide array of diversity efforts and programs, and participating in the greater Boston community.

For more than 140 years, The Winsor School has empowered generations of girls to pursue their aspirations, discover new talents, hone critical skills, and contribute to the world. Serving students in grades 5 through 12, Winsor is unwavering in its commitment to developing students of conviction with strong voices and expansive intellectual capacity. That same intellectual depth and passion for learning define a faculty whose members, with an average tenure over 20 years, bring extraordinary expertise, commitment, and enthusiasm to their teaching.

Located in the Longwood neighborhood of Boston near Fenway Park, Winsor attracts and nurtures students who are authentic, joyful, energetically curious, and academically confident. Says one faculty member, “Winsor students let you take them on intellectual adventures.” While academic excellence is at its core, the classroom experience is just the beginning. Students are not only thinkers and scholars but also athletes, artists, community volunteers, club members, leaders, mentors, and friends.

In 1886, Mary Pickard Winsor opened a six-month school for eight girls at 334 Boylston Street in Boston’s Back Bay, the first of six locations in various townhouses in the neighborhood. Ahead of her time, Miss Winsor wanted to prepare women to be self-supporting and hoped they would be competent, responsible, and generous-minded. By 1900 the student body had grown to 99 girls;

in 1910 the school relocated to its current location in the Longwood area. Now serving 474 students on a single campus, Winsor’s state-of-the-art facilities, including the Lubin-O’Donnell Center for the performing arts, athletics, and wellness, which opened in 2015, reflect and enhance the excellent education each student receives.

The head of Upper School is a central presence in the life of Winsor, providing thoughtful, student-centered leadership to a dynamic community of adolescents, faculty, and families. In a school known for the strength of its relationships, intellectual ambition, and deep commitment to its students, the head of Upper School helps create the conditions for students and faculty to do their best work and for the Upper School to flourish as an essential part of the larger 5–12 community.

Working closely with the head of school and senior leadership team, the head of Upper School will help shape Winsor’s future while honoring the traditions, values, and distinctive qualities that make the school special. This is a role that calls for vision and follow-through, warmth and accountability, and the ability to attend to both the big picture and the details of daily school life.

A close partner to the head of Lower School (grades 5-8), the head of Upper School reports jointly to Assistant Head of School, and Head of School, Meredith Legg who joined the Winsor community in July 2025. The next head of Upper School will bring energy,…