Fall 2026
In This Issue
140 Years and Counting
From the chime of Miss Winsor’s Bell to the boisterous joy of Ring Day and UTL, Winsor’s traditions have shaped generations of students. In honor of 140 years, we celebrate the traditions, objects, and events that make Winsor, Winsor.
Leading the Field: A History of Athletic Leadership
How did Winsor go from calisthenics on Boston Common to 14 competitive teams and dozens of championships? Meet the often-unsung leaders who built the athletics program, expanded opportunities for girls, and shaped what it means to be a Wildcat.
Looking Back, Moving Forward
After a year spent listening to students, Head of School Meredith Legg P’32 reflects on the friendships, confidence, and intellectual growth they described, and on how Miss Winsor’s 140-year-old spark still lights the way forward.
Bulletin
A visit from Little Rock Nine member Dr. Terrence Roberts. The student-led Asian American Footsteps Conference. A first-ever Spring Rally and a brand-new civics curriculum. Across campus this year, Winsor students found connection, community, and their own voices.
The Gift of a Lifetime: Introducing The Marion D. de B. Kilson ’54 Endowed Scholarship Fund
Marion Kilson ’54 came to Winsor as a scholarship student. Now her children are opening that door for others, creating an endowed fund for students with financial need who would be the first in their families to attend an independent school.
A Lifelong Habit of Helping
Annabel Jones ’27 started by baking cookies for her local firefighters. Today her service reaches across Boston, from building mobile gardens and tutoring fourth graders at the Tierney Learning Center to telling the stories behind local composting work.
Winsor Giving: Part of an Intellectual Odyssey
Three generations of F. Warren McFarlan P’92’s family have called Winsor home. For three decades, the Harvard Business School professor emeritus has given back, lending his governance expertise and his family’s steady support to the school’s mission.
Exploring The Winsor Bulletin’s Publication History
In 1934, the very first Bulletin offered graduates school news, classmate updates, and use of the tennis courts (with ID). Winsor Archivist Chelsea McNeil traces how the magazine has informed and connected our community for more than 90 years.
Commencement
With a fairy-tale class theme, a song about friendship, and wisdom from nuclear technology CEO Dr. Leslie Dewan ’02, the Class of 2026 closed its Winsor chapter, celebrating with one moonwalk and a flurry of 65 red roses.
Continuum
From volunteering side by side and exploring art after dark to earning statewide honors and coming home for Alumnae Weekend, Winsor graduates prove that the bonds formed on Pilgrim Road last a lifetime, across every class year.
I Felt Ready for the Next Step
Nina Gerson ’27 spent a semester in Washington, D.C., at the School for Ethics and Global Leadership. She shares how the experience connected her passions for politics and journalism and gave her a clearer vision of her future.
