Thankful for Grandparents and Grandfriends
Eager older learners streamed into the Wildcat Room ready to start their school day at Winsor’s annual Grandparents’ and Grandfriends’ Day event. The special program brought more than 160 visitors to campus the day before Thanksgiving break.
While the whole school enjoyed a festive morning snack of cinnamon sugar donuts, students with grandparent and grandfriend visitors joyfully gobbled their sweet treats together. As mobility and lesson plans allowed, a cohort of students left snacktime with grandparents and grandfriends in tow. On their way to class, students offered bespoke tours pointing out lockers and indicating favorite spots on campus.
In preparation for all the visitors, Winsor’s dedicated facilities team set up dozens of extra chairs in classrooms all over campus. All told, faculty incorporated over 100 golden-age learners into the day’s lessons. As grandparents and grandfriends settled in—some even pulling out notebooks and raising hands—they were able to participate in hands-on learning and witness the rigorous excitement of a Winsor education first hand.
Grandparents and grandfriends joined courses such as Truth and Fiction, Middle Eastern Literature, Native American Literature, Information Sciences, Biology, Honors Geometry, and Precalculus. In Class II Science, the lesson of the day was a chicken wing dissection, which garnered enthusiastic participation by grandparents and grandfriends who wore gloves and wielded instruments. The World Languages Department hosted a number of folks as well with visitors to classes in Mandarin Chinese 2, Class IV French, and Class IV Spanish. In Class IV Latin/Accelerated Foundations of Latin, World Language Faculty and Winsor alum Caroline Burke ’07 incorporated Winsor’s urban campus location into her lesson plan, taking the class on a walking tour to spot classical architecture around Boston.
While some visitors attended classes, others heard from a student panel composed of seven Upper Schools students. The panelists shared stories of favorite Winsor traditions, teachers who go above and beyond, clubs that add to the Winsor experience, what it’s like to participate on sports teams and in theater productions, and—of course—the best school lunches.
Chef Heather is both a beloved and award-winning figure on campus. Aside from the donuts, grandparents and grandfriends also partook in a delicious luncheon prepared by Chef Heather and the dining services team at Winsor. Guests enjoyed a festive salad course featuring local lettuce, roasted butternut squash, spiral beets, and candied pumpkin seeds, a choice of entrée—orange-tarragon Statler chicken breast or orange-tarragon honey nut squash with lentils, and mashed potatoes and green beans with maple mustard sauce. Dessert was classic Winsor: our signature brownies, as well as some delicious cookies to round out the meal.
The lunch program included a performance by Class IV Rock On, who wowed the crowd with historic American soul: James Brown’s “I Got You (I Feel Good).” Afterward, Head of School Meredith Legg P’32 shared remarks with the gathered group, including reflections on her first fall at Winsor. She spoke about her unexpected path from engineering to girls’ education, and her deep belief in the transformative power of girls’ schools, noting, “This is a place where girls can shed their self-consciousness.” She went on to talk about the singular experience Winsor students enjoy during their time here, the excellence of Winsor’s faculty who “scaffold and develop deep analytical thinking, creativity, and problem solving,” and the bright future the school looks toward as we write the next chapter of our history.
As the afternoon drew to a close, the campus hummed with the lingering energy of shared discovery and connection. Grandparents and grandfriends departed with fuller notebooks, new memories, and a deeper glimpse into the joy, rigor, and community that define a Winsor education. For students, the day offered a rare and treasured chance to welcome loved ones into their daily world. They shared the classrooms where they think boldly, the halls where they grow together, and the traditions that shape their Winsor experience. It was a celebration not only of learning, but also that the strength of our school is built, in no small part, on the love and support of the people who walked beside our students long before they walked through our doors.





