The Largest Grandparents and Grandfriends Day in Winsor History

November 21, 2023—Ahead of Thanksgiving break, over 120 grandparents and grandfriends visited campus. Older friends and relatives were all smiles as they walked through the halls to participate in the annual event—the largest Grandparents and Grandfriends Day in Winsor history. 

To kick off the morning, students and their visitors gathered in the Wildcat Room for a special snack of glazed doughnut holes and apple cider. Sitting together at round tables, chatting and taking selfies, students and visitors enjoyed a memorable break between classes where school life and home life blended together. 

Some grandparents and grandfriends lingered to hear from a student panel moderated by Eva LaFond ’24 with Karla Sahin ’24, Aleena Bacorro ’25, and Beatrix Picotte ’24; others excitedly accompanied students to class to see a Winsor education firsthand. Students on the panel took turns sharing stories about clubs, classes, sports, faculty, and the intangibles that make their Winsor experience special—like arriving to campus early by train to enjoy a quiet morning on a special hallway bench, taking bass lessons in the After-School Music Program, and dropping into clubs and affinity groups. 

Bacorro spoke about her experience reading classics like The Color Purple and The Great Gatsby in English class, while LaFond highlighted electives like Literature of the Mind—a class that tackles texts that deal with complex mental questions of the self and the consciousness. “We’re just so lucky to get to take classes like that,” LaFond explained. 

Sahin highlighted the level of choice students have. In Class VII the juniors take Global Studies, an interdisciplinary program where English and history courses focus on the same region. Sahin picked a track that focused on Africa, but other choices include India, Latin America, the Middle East, and Russia.
Picotte shared with grandparents and grandfriends that Winsor students know “it’s okay to ask for help, and you should do that as part of the learning process, and figuring out what you need.” 

Unanimously, the panel of students agreed that Winsor traditions such as Under the Lights and Spirit Week were fun in part because of the commitment and participation of an incredibly engaged faculty body. When it comes to dress-up themes, “the teachers go all out, it’s amazing,” they said. 

Faculty welcomed grandparents and grandfriends to observe and participate in lessons and conversations. Excitement was high, especially for grandparents and grandfriends who haven’t experienced a classroom learning environment for decades. Visitors tagged along to familiar courses of yesteryear—such as middle school history, English, science, algebra—and also courses they had never experienced such as sculpture; animation; Broadway Bound; and Drum, Strum, and More. Some grandparents and grandfriends took their time in the classroom very seriously and returned to the Wildcat Room with pages of handwritten notes! 

The afternoon program continued with a festive luncheon. The meal was peppered with musical numbers from performing arts courses such as Illumina and the Chamber Players. In her remarks, Head of School Sarah Pelmas elaborated on the founding history of Winsor and why there is such an emphasis on ways to find connection and belonging.

“We know that students learn better when they feel safe, seen, and challenged. They have to find activities that matter to them, and they have to believe that they matter to each other and to the school itself. When they feel that level of connection and belonging, then learning is much easier, ” said Ms. Pelmas.

She went on to explain that grandparents and grandfriends play an important role in supporting and nurturing students. “The beauty of grandparents and friends is that your students know you will always love them and always be there, and they turn to you for that steadfastness. You can help them ride the ups and downs of their experiences just by asking about their day, about their friends, activities, successes, and goals. They know that it’s never in doubt how much you love them, how proud you are, and that you know it’s hard sometimes. You have the wisdom of experience, and the generational gift of not being their parents. You are basically magical.”