Celebrating the Class of 2026
Nearly 1,200 people were in attendance for Winsor’s 132nd commencement ceremony on June 9 to honor the 65 members of Winsor’s Class of 2026. Family and friends, teachers and classmates, and Classes I–VII—graduates’ whole extended community—gathered to celebrate the hard, rewarding work that led them to this milestone. The ceremony was also an opportunity to look toward life’s exciting next steps, and to all the ways Winsor will stay with these new alums all along life’s journey.
Faculty, staff, and students processed into the massive white tent that covered most of Winsor’s courtyard; the faculty and staff accompanied by Advanced Rock On’s rendition of “Don’t Stop Me Now” by Queen, and the students walked in to Bach’s famous composition, “Jesu, Joy of Man’s Desiring.”
Once the tent was full, Head of School Meredith Legg P’32 welcomed the assembled community and acknowledged the ways in which everyone there had played a role in this day’s accomplishments.
“These commencement exercises honor the 65 graduates of the Winsor School Class of 2026. This ceremony is also a moment to recognize all of those who walked beside you on your journey, graduates,” said Ms. Legg. She noted “the faculty and staff who work tirelessly to create the learning community you have known and cherished during your time at Winsor,” and she credited “the families, the parents, grandparents, siblings, aunts and uncles, caretakers and friends” who believed their child belonged at Winsor and “knew that this Winsor education would be the gift of her lifetime.” The graduating class met these sentiments with enthusiastic applause.
After Ms. Legg’s welcome, Yemisi Adetowubo ’26 and Alisa Ross ’26 read a passage selected by the senior class from A. A. Milne’s The House at Pooh Corner. In Milne’s scene, Christopher Robin asks Pooh to promise he’ll never forget him, “not even when I’m a hundred.” After Pooh promises, the narrator reflects that, though they may leave that place, “wherever they go, and whatever happens to them on the way, in that enchanted place on the top of the Forest, a little boy and his Bear will always be playing,” drawing a moving parallel to the seniors’ enchanted Winsor experience and to their class theme, “Once Upon a Time.”
Led by Choral Director Andrew Marshall, Illumina then performed “Blessing” by Katie Moran Bart, based on the old Irish verse. “May the sun shine warm upon your face,” the Upper School choir sang to the seniors on their warm and cloudless graduation day.
Following this performance, Allison Kaneb Pellegrino ’89, P’21, ’22, chair of the Winsor Board of Trustees and president of the Winsor Corporation, addressed the Class of 2026. She commended this year’s seniors, in particular, for serving as a crucial resource of institutional knowledge for Ms. Legg in her first year as Winsor’s head of school. Ms. Pellegrino also stressed “how truly special” the Winsor community is, and encouraged the graduates to think of that community as “part of your permanent infrastructure.” Going out into the world after graduation was not leaving Winsor, but rather, “expanding your territory.” She explained that “being an alumna is like having a permanent safety net”—meaning something more than simply a professional network, “but a social and emotional one,” she said. “Winsor is always here for you.”
Before Ms. Legg returned to the podium to address the graduating class and their families, the whole student body stood to perform the senior class song, “We’re Going to Be Friends” by Jack White, originally performed by the White Stripes.
Ms. Legg’s remarks followed on the song’s themes, saying “We’re Going to Be Friends” “encapsulates the way you have approached your time together, seniors: with a magnetic warmth, pulling all of us into your orbit. With a knowledge that anything that is worth doing is worth doing together, that sharing the experience of your triumphs and challenges makes those experiences sweeter. And, with wonder—that insatiable curiosity, that thirst for knowledge, that appreciation for the world expanding before you.”
She traced the way that this wonder has informed the senior class’s time at Winsor, from their Class I theatrical production of Where the Wild Things Are, to their Class IV Shakespeare performance, The Tempest, “where again you explored the themes of man and monster, magic and science, and justice and forgiveness.” Ms. Legg recounted some of the class’s many memorable high school moments, from athletics to robotics to ILEs, summing up, “You have put your hearts and minds into leveling up to reach every challenge.”
She then turned to the senior class theme, “Once Upon a Time,” and examined, at the end of this class’s fairy tale, the concept of “happily ever after”: “We who know you, seniors, know that your Happily Ever After is something much deeper,” she said. “Yours is a pursuit of purpose and of knowledge. An awareness that contributing to the world is what will bring you fulfillment and a true happily ever after.”
Ms. Legg concluded her address by quoting once more from the senior song: “Our wish for you is this: That you will hold on to that sense of wonder that makes it so that ‘we don’t notice any time pass.’ And that you will seek out the people—like your friends at Winsor—where you can just tell ‘we are going to be friends.’”
The gathering then joined in a performance of Winsor favorite “Jerusalem,” an adaptation of William Blake’s poem about tirelessly striving to build a better world, with music by C. Hubert H. Parry, accompanied by Head of Performing Arts Felicia Brady-Lopez on piano and directed by Mr. Marshall.
Each year, the seniors select a representative from their class to speak at commencement. Alessa Andrews ’26, this year’s chosen senior speaker, stepped up to the mic and addressed her classmates, bringing them back to the deliberations over their class theme during their junior retreat on Cape Cod. “In order to succeed,” she said, “we had to listen carefully to one another, understand each other’s motivations, and close the gap between many diverging viewpoints. Even through the grogginess, lost voices, and chaos, we managed to come to a consensus on the theme: Once Upon a Time.”
The point in remembering this moment, Alessa said, was to remind everyone that “this class is not one personality or one perspective,” but “when it mattered,” they were equipped with the skills to “come together.” At this same retreat, the students chose five words to represent their class: “United, supportive, spirited, reliable, and motivated.”
“Throughout the year,” she said, “even when we faced challenges and were pulled in different directions, we kept these words in our heads to guide our actions.”
She credited the class’s ability to reach the end of their fairy tale to both resilience and dedication to these values—along with “help from our version of fairy godmothers: our teachers, the Winsor administration, the facilities team, and the kitchen staff, who were all working hard to ensure our success.”
Nearing the end of her remarks, Alessa charged her classmates: “As we create new communities, we must replicate the lessons we learned and the moments that made our class great. Find things you can agree on, like the fairy tale theme. Build a community around your core values, and bring them to life in all of your experiences. And remember that once upon a time, in what we call Winsor Castle, we created a united, supportive, spirited, reliable, and motivated group out of 65 wildly different people.”
After Alessa’s stirring remarks, Senior Small Chorus performed their final song together as an ensemble. As they sang Paul Simon’s classic ballad “Bridge Over Troubled Water,” many in the ensemble and the audience dabbed tears from their eyes.
Senior Class President Liana Min ’26 introduced this year’s commencement speaker, Dr. Leslie Dewan ’02, CEO of the nuclear technology consulting firm Neutronic Designs. Liana recounted Dr. Dewan’s impressive credentials: a Ph.D. in nuclear engineering and a Presidential Fellowship from MIT; a Department of Energy Computational Science Graduate Fellowship; service on the MIT Corporation, MIT’s board of trustees, and the committee for the National Academy of Engineering’s study “Laying the Foundation for New and Advanced Nuclear Reactors in the United States”; named an MIT Technology Review “Innovator Under 35,” a National Geographic Explorer, and a World Economic Forum Young Global Leader.
But more personally, Liana recounted her impression of Dr. Dewan from the Zoom conversation she and her classmates had with the speaker earlier this semester. “While her accomplishments are extraordinary, what impressed us most was the authentic joy she brought to the conversation,” Liana said. “Dr. Dewan met every question we asked with one of her own, replying with genuine interest and sharp wit. That curiosity has undoubtedly fueled her success as an engineer, innovator, and leader.”
“I’m so glad to be back at Winsor today,” Dr. Dewan began, “and incredibly grateful to be able to celebrate this day with you all.”
Dr. Dewan’s remarks covered a range of subjects relevant to the graduating class. She described, for instance, the “pre-nostalgia” of high school’s final days—“that strange awareness, while you’re still living through something, that you will remember it, and that it will matter deeply to you for a very long time”—a feeling surely most of Class VIII could recognize. But the majority of Dr. Dewan’s speech revolved around the linked topics of joy, curiosity, and connection.
“In a world that often rewards cynicism, it is easy to underestimate joy,” she said. But joy “is what makes meaningful work possible. It’s what brings people together; it’s what sustains communities; and it’s what reminds us that the whole point of building a better world is that people might actually enjoy living in it.”
That work of bringing people together—what Dr. Dewan called “a gift for connection,” is also essential to building that world, and it’s a skill the Class of 2026 “has in abundance.”
She described how important making those sorts of connections has been to her own career. “Twenty-four years ago, when I was sitting where you are today, I knew I loved science and engineering. I suspected that my future would involve reactors, materials, equations, and technical problems,” she said. “I did not expect how much of my career would come to depend on connecting with people.”
“The technologies we build do not exist in isolation,” Dr. Dewan explained. “They affect communities, governments, economies, and people’s lives. They require trust. They require conversation. They require the ability to explain complicated ideas clearly, and to listen carefully when other people see the world differently than we do.”
This work has demanded a “moving between worlds,” she said. “And when I think about where I first learned to do that, I think about Winsor.”
Dr. Dewan identified this aptitude for well-rounded understanding, curiosity, and boundary-crossing communication as a hallmark of a Winsor education. “One of the greatest gifts that Winsor gives us is not simply knowledge,” she said. “It is the ability to move comfortably between different ways of thinking and different ways of being in the world. To be analytical and creative. Scientific and humanistic. Rigorous and compassionate. That ability has become even more valuable as the world has grown more complicated.”
In closing, Dr. Dewan left the Class of 2026 with a request:
“Protect your sense of wonder, your joy, and your curiosity. Keep creating community and connection wherever you go. Carry forward the habit of explaining what you know clearly and generously, because some of the most important work you will ever do will involve helping other people see something they could not see before. And carry forward the breadth that Winsor has given you: the ability to move among fields, among communities, and among different ways of thinking,” she said. “And wherever life takes you next, know that Winsor goes with you.”
Once Dr. Dewan’s remarks had concluded, the time came for each member of the Class of 2026 to walk (or in one case, moonwalk) up to accept their diploma onstage, receiving hugs, high-fives, and/or proud nods from Ms. Legg, Class VIII Dean David Griffin, and Head of Upper School Kimberly Ramos.
“Friends and family, on behalf of the faculty and staff, and the trustees of the Winsor School, I present the graduates of the Class of 2026,” said Ms. Legg, which was met by the applause of some 1,200 community members and a flurry of 65 red roses tossed into the air.
Congratulations to the Class of 2026!
