By Joan Yenawine
Joan is a writer and contributor for Winsor’s Communications team.

We want every single student to feel that this is their school, to think, ‘I belong here.’ ”

— Sarah Pelmas, head of school and O’Donnell Family Chair
Head of School Sarah Pelmas’s bold statement has a fresh, modern ring to it. Yet the core value of belonging has long been a part of Winsor’s DNA. “At every moment when there was a shift in who the population of the school was, there has been some kind of thinking about belonging. So it’s not at all a new thing. The whole school is organized around making sure students feel they can bring their entire selves,” Ms. Pelmas says.

“It’s about people feeling like this is their place.”

After all, to develop the confidence needed to learn, a person first must feel comfortable and safe. Belonging, therefore, is crucial for every learning environment. Because Winsor has emphasized the goal of belonging for so long, the school is practiced at helping students find points of connection with others.

The advisory program is central to helping classmates become known both to one another and to faculty. In these small-group structured weekly meetings, adults and students discuss everything from serious academic and future plans to not-so-serious topics like K-pop or the finer points of Pictionary. As participants spend this time together intentionally, understanding and trust can grow.

“In an informal setting, I feel more comfortable being vulnerable and honest,” Alyna Johnson ’27 says. “Regardless of the activity, advisory connects me with classmates I might not have otherwise have befriended.”

Schoolwide traditions, including both regular elements of the academic day and highly anticipated events through the year such as off-campus trips, reveal even more of Winsor to students. These shared activities help cement classmates, faculty, and staff to one another.

Nora Furlong ’25 recalls how welcomed she felt from her very first day in Class I, as she ran through the “scream tunnel” of Upper School students. Hattie Jackman ’29 found that same sense of community through the annual Red Day: “The whole school comes together and shows spirit. Whether it’s watching one of the games or eating the amazing food, on Red Day, everyone has fun.”

Athletics is still another forum for connection—the collective sense of purpose, striving, failing, and winning together. That surefire combination creates lasting bonds, even among kids who aren’t the fastest or who are relatively new to a sport.

Raina Sohur ’23 says she discovered the joys of the cross country team when she was in Class III. “I love the team because I felt like I belonged and was included equally from when I was a slow seventh grader to being a senior on varsity,” she says.

And for still other students, belonging to Winsor comes not through the people but through the spaces—personally resonant spots on campus such as the Lubin-O’Donnell Center lounge and the courtyard—where one feels fulfilled and at peace, perhaps with others or perhaps alone.

The dynamic of belonging is a tricky business to untangle. There is much to sort out and understand before a community of hundreds—with different backgrounds, identities, and perspectives—can come to know and appreciate one another. Ms. Pelmas describes this “diversity of viewpoints and our differences as a fundamental part of what it means to belong.”

Julian K. Braxton, Winsor’s director of community and inclusion, says he tells students, “You must venture out and create your own spaces of belonging and include people who may not always agree with you. ...In our disagreements, we can find ways of understanding each other.”

And no school—no matter how thoughtfully designed and organized its curriculum—can completely eliminate the normal growing pains of adolescence. “There are a couple of key times in life—usually around seventh grade and again at 10th grade—where significant identity formation starts happening because there are massive brain changes,” Ms. Pelmas says.

“When people look back on middle school, they remember they felt out of place, they didn’t know who they were. You have to go through some rough patches, but it’s utterly crucial to who you are. We try to reinforce for kids that this is normal, that it’s necessary.”

Associate Head of School Kate Caspar says the only way to know whether Winsor is getting belonging “right” is for faculty and staff to stay closely connected to their students. This is where Winsor’s small size has an outsize impact.

“This is my fourth independent school, and I think one of Winsor’s great advantages is that we are small,” says Ms. Caspar. “We really know our students. We see them in class, we see them in clubs, activities, and advisories. I think every student here has a connection with an adult here, and it’s through those meaningful, trusted relationships that the best teaching happens.”

Belonging fits easily alongside diversity, equity, and inclusion as related educational goals. Indeed, Winsor’s 2021 Report on DEI concludes with the statement, “We remain steadfast in our commitment to belonging.”

But, Ms. Pelmas cautions, the terms are not interchangeable.
“Diversity is typically numbers—who is physically there. Equity is
about ensuring access to the support needed to attain similar outcomes. And inclusion is the validation of particular identities and background,” the head of school says. “Belonging is very different because everybody has such an individual sense of what it feels like to belong or what it would mean for them to belong.”

Being part of a high-achieving institution carries its own, special
challenge. “The level of ambition can create anxiety, which is contagious,” says Ms. Pelmas. “The kids feel it, the parents feel it. ...The kids are constantly worried about not measuring up. We spend a lot of time talking about that, because that can really make kids struggle with who they are and their self-concept.”

Talking. Building relationships. Offering opportunities and choices. These are the time-intensive, creative, and intuitive ways that everyone at Winsor pursues creating a sense of belonging.

“There’s good work to do here,” muses Ms. Pelmas. “In a school like this, it’s easy to feel that we’re making a difference, because these kids are going to change the world. They’re going to be strong. They know what matters to them. You can feel that here.” 
Off-campus retreats to Hale Reservation, overnight trips to Cape Cod, daily meals in the dining room, and self-directed free periods provide students with a precious resource: time to cultivate connections.

There is space to create a personal and collective sense of belonging at Winsor, and students find it with teammates in athletics and with classmates and faculty during advisory. 

Class retreats at the beginning of the school year are one way students and faculty forge a bond. By the time students in Class VIII are about to head off to college, they seek out their favorite teachers and revel in each other’s company.