Connecting Outside the Classroom

Each September, Winsor students leave the classroom behind and head off campus for class retreats. “It is really special that Winsor builds time in our schedule to have some fun as a class!” shared a Class VI student. 

Creating and fostering community is a hallmark of the Winsor experience. In support of that mission, class coordinators, deans, and advisors accompany students on a fall class retreat where the entire 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, students head to Hale Education in Westwood, MA for team-building, outdoor adventure, and class bonding both with their grade and their buddy class. 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. 

“I was super scared to climb the ropes course,” shared Class I student Christine Ihua ’33, “but everyone was cheering for me and being so supportive.” Other activities like blindfolded trust walks helped students to get creative and practice communication skills.

Class II boarded a bus to Good Pickin’ Farm in Westford, MA for a day of hiking, goat yoga, and building connections while Class III students spent the day at Community Harvest Project, a non-profit organization that is dedicated to addressing food insecurity through sustainable farming practices and community engagement. Class III visited the Brigham Hill Community Farm location, which grows fresh fruits and vegetables for hunger relief and engaged in a hands-on farming experience in North Grafton, MA.

To jumpstart their time in the Upper School, Class V always spends two days together at an overnight retreat. This year, ninth graders traveled to Wavus Camp in Jefferson, ME where Class V Dean Dana Martin designed a program for students to come together as a class and develop a sense of community as they begin their high school experience. Multiple Class V students remarked on the meaningful downtime with classmates where they could hang out, play cards, share stories, and stay up late “without the distraction of screens.” One student shared that her favorite memory of the trip was “talking about politics, culture, and religion with my cabin mates until 12:08 a.m.” Another student enjoyed “the opportunities to make new friends and become closer with my current friends.” Adding, “Whether it was through Uno games or bonding during meals, I connected with different people throughout this trip.”

Class VI ventured to downtown Boston, spending the day at the New England Aquarium, getting lunch in Quincy Market, and walking around Faneuil Hall. In Class VI, students are assigned a dean who will be with them for every step of their high school journey. Class VI Dean Jenny Albright invited advisory groups to have lunch together and explore the area with friends. While students enjoyed the Shark and Ray Touch Tank and the scavenger hunt, the less structured periods “where I could just hang out with people from my grade and walk around Boston” were universally appreciated. 

“I haven’t ever been able to ‘go out’ with all of [my friends] before,” explained one student. “It will be one of my favorite memories of this year and especially from the retreat. It allowed me to connect with them on a deeper level than I have before and cemented our relationship even more.”

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.