A Strong Sense of Community 

“When the whole grade gathered around the campfire, ate s’mores, and sang songs, I felt such a strong sense of community right then,” said a Class V student.

Following Convocation and a busy first week of school, Winsor students stepped away from their desks, left the classroom behind, and headed off campus with their entire grade. 

Creating and fostering community is a hallmark of the Winsor experience. In support of that mission, class coordinators, deans, and advisors accompany students on fall class retreats where each grade participates in a full-day outing. These trips not only build friendships, they help students understand who they are as a class and what unifies them. 

In the Lower School, Class I and Class IV are buddy classes. A bookend to the beginning and end of Lower School, both classes spent the day at Hale Education in Westwood, MA. English Faculty and Class I Coordinator Lisa Stringfellow enjoyed watching Class IV bond with their Class I buddies over lunch. “Having taught the older students when they were in Class I, it was a wonderful full circle moment and a special tradition at Winsor,” she shared. The tradition leaves a lasting impact on students too. Jade De Los Angeles ’34 recalled, “my favorite [retreat] memory was when I met my Class IV buddies and they were really nice. They really seemed excited to meet me and have lunch with me.” 

At Hale Education, activities focus on team-building, outdoor adventure, and class bonding. The experience provides an excellent opportunity for students to learn from and with each other as they take risks and support classmates in their endeavors. During one activity, students swing on ropes blindfolded and everyone had to help each other avoid crashes. “We had to work as a team,” explained Nisa Ghelani ’34. After a near fall, Anisa Shah ’34 recalled, “everyone cheered for me and I was able to finish.” Assistant Director of the Virginia Wing Library and Class I Coordinator Danielle Smogard noticed the energy too. “It was such a supportive and joyful time. I think it really set the tone for how Class I will support one another during their first year at a new school.”

Class II students ventured to Good Pickin’ Farm in Westford, MA where they enjoyed hiking, goat yoga, and building class connections. “Our trip was a great way for new and returning students to get to know each other in a low-stress environment,” says History Faculty and Class II Coordinator Annie Huntoon, “sitting with animals, having lunch with new friends, and laughing on the bus were all great ways to start the year.”

Timed to America’s semiquincentennial and grounded in the Class III civics curriculum, students visited the Boston Public Library in Copley Square to view a special temporary exhibition—Declarations: Printing a New Nation. For the first time ever, the library’s eight rare printings of the Declaration of Independence were displayed together. Alongside rare maps, early printings, books, and visual materials from the period, the exhibit explored the summer of 1776 when the Declaration was current, breaking news. Winsor students stepped into that moment and then applied it to their own community values, considering what values people and nations choose to put into writing, and where personal, community, and national values align or come into tension.

To begin their years in the Upper School, Class V students traveled to Camp Mataponi for an overnight retreat on the shores of Lake Sebago in Maine. Students enjoyed ropes courses, a scavenger hunt, and an egg drop challenge. But in an anonymous collection of memories, the little moments—s’mores, singing songs by the campfire, frolicking in the grass, late night talks with friends, getting closer to cabinmates—were mentioned more than anything else and will undoubtedly have ripple effects throughout the school year. “I didn’t know some of the people in my bunk as well, and getting to talk in a more relaxed setting really helped me to get to know them better and make new connections,” shared one Class V student. Another explained, “I will carry the friendships that I made during the retreat” through the year. 

Class VI students visited the New England Aquarium for their annual retreat, building a sense of community in their new advisory groups and coming together as a class. Activities like the Shark and Ray Touch Tank are always a crowd favorite!

After fall retreats, students continue to build upon and cultivate connection throughout the school year. Winsor supports dedicated community time, which is built into the morning and afternoon schedule, ensuring students take a break from academics to gather both with classmates and across grades at all-school assembly, in homeroom, during advisory, and in clubs. 

Later in high school, after years of class retreats and community time, juniors and seniors continue to nurture bonds in other ways. One of the highlights of junior year is an April overnight retreat to Craigville in Centerville, MA. The retreat helps the class reflect on who they are as a group and what kind of community they want to create in their senior year. Class VIII will have Senior Circles in May and June where classmates gather and support each other as they prepare for life beyond Pilgrim Road.