From the Head of School Spring ’26

After six months on Pilgrim Road, I have settled into the day to-day rhythm of life at Winsor. Each morning, as I ascend the entryway steps I am welcomed to campus with a cheerful “Good morning!” from Ms. Marshall. I often stop for coffee and a quick hello to Chef Heather in Peter Hall before settling into my office for meetings and correspondence. On my way to and from lunch, I take the circuitous route to walk down the hallways and get a glimpse into the happenings in classrooms and greet students.
I join the faculty at lunch and hear stories of the classroom discussions that morning, the lab experiments getting set up for the afternoon, or the upcoming game or field trip. The depth of our faculty’s expertise and dedication never ceases to amaze me, even in these casual conversations.

In the late afternoons I open my office door to hear the sounds of the end of the school day: the farewells and laughter of friends as they head to after-school activities. I find these reassuring sounds of a bustling school calming each day, and I miss these familiar noises during breaks. I stop by home games to cheer on our Wildcats as they compete with strength and resolve. Ending my day is a quick check-in with the facilities team, who—amongst many other responsibilities—keep our after-school pick up running quickly and smoothly each evening.

My internal clock is now set to look forward to the Winsor weekly milestones. On Mondays, it’s the afternoon Upper School
meeting. On Fridays, campus is buzzing in advance of our weekly assembly. These community moments bring a special joy to the week, whether they are student performances or outside speakers. I speak regularly at assembly to our entire community, and this year I have been answering questions from students in a segment I call “Legg’s Letters.”

Halfway through my first year, I find myself moving to the special and unique rhythm of Winsor. It is a beat that can’t easily
be explained in words, but it quickly becomes a part of you when you live it each day. It is a feeling as familiar to Class I students as it is to alums in the 50th-reunion class. It is punctuated by the sounds of arrivals and departures, carried along by students passing between classrooms and connecting with faculty, underscored by the thousands of Winsor women who have passed through these halls. The Winsor rhythm is strong, and returns right on time with the arrival of students at the start of each day.

—Meredith Legg