A Special 5th Reunion Dinner for the Class of 2020

The Winsor Class of 2020 had an unusual final spring semester, celebrating their graduation and many other events virtually even receiving their diplomas in festive, albeit a socially distanced, event on the turf. During Winsor Alumnae Weekend 2025, the Class of 2020 finally gathered with their families for a special fifth-reunion dinner that brought some class members back to Pilgrim Road for the first time since March of their senior year. 

Outgoing Head of School Sarah Pelmas welcomed graduates and their families to open the dinner, acknowledging the unique (if challenging) experience of being part of the Class of 2020. Ms. Pelmas emphasized the ways their pandemic experiences made this class stronger, more resilient, and more adaptable—all qualities that have served them well in their years since Winsor, and will continue to be valuable as they navigate a changing world. Ellen O’Hare ’20 echoed Ms. Pelmas, emphasizing her gratitude at being part of “the vibrant, dynamic community that is our class—each person bright, multi-dimensional, beautiful in exactly their own way.” She thanked Winsor for the gift of “unshakable confidence in myself as both a young woman and a passionate learner.” Maggie Furlong ’20 added that while “our class photo downstairs would look different from all the others,” Winsor has remained a special place for her and many of her classmates. She then led a toast “to getting the celebration we deserved all along.” 

The night included a viewing of the class’s senior slideshow, featuring photos and memories from Class I through Class VIII. Many of the class’s faculty advisors also joined the dinner, relishing the opportunity to reconnect with former students and their families. The night ended with a beloved Winsor tradition: a “death by chocolate” dessert bar, which provided a sweet conclusion to a rich experience for the Class of 2020.