2026 Awards Celebration
Gathering in the David E. and Stacey L. Goel Theater on June 4, the Winsor community came together for the 2025–26 Awards Celebration, recognizing students for excellence in athletics, academics, the arts, leadership, and service.
As in years past, the celebration featured one of Winsor’s most beloved traditions: surprise award announcements. With families of award recipients seated in the balcony and more than 40 prizes to be conferred, students waited to learn the winners alongside their classmates. Many of the awards recognize achievement demonstrated throughout the year, while others—including the Brooks Poetry Prize and Hemenway Prize for Public Speaking—follow competitions held before the full community earlier in the school year.
Welcoming students, faculty, staff, families, and guests, Head of Upper School Kimberly Ramos reflected on the significance of the day.
“While today’s awards recognize a relative few,” she noted, “as you cheer loudly for your peers, you are also cheering for our entire community.” She encouraged students to recognize the many ways they support one another throughout the year and to take time to express gratitude to those who helped them along the way. “Winsor is stronger because of each and every one of you,” she said, thanking the Class of 2026 in particular for leading the community “with creativity, passion, and care.”
The celebration began with the conferral of athletic awards. Head of School Meredith Legg P’32 highlighted another remarkable year for Winsor athletics, including two Eastern Independent League championships, three league players of the year, three league coaches of the year, multiple individual league champions, and a series of school, league, and regional records in swimming and track and field.
“These accomplishments were made possible by the incredible work of our athletic teams and coaches,” Ms. Legg said before presenting the athletic prizes alongside Athletic Director Sherren Granese.
The ceremony continued with academic, arts, community, and leadership awards. Reflecting on her first year at Winsor, Ms. Legg shared an observation she had heard repeatedly from faculty: that Winsor students genuinely enjoy tackling difficult challenges.
“At first I thought, ‘sure…keep telling yourself that, teachers,’” she joked. “And then I spent time with all of you. And you told me and you showed me over and over again. You love a challenge. Even more than that, you love triumph over challenge.”
Ms. Legg praised students’ intellectual curiosity and willingness to stretch themselves, describing the community as one that embraces growth through effort. “When you read the harder book, write the more complex sentence, try the spicier math problem, build the more elegant experiment—you are growing and strengthening your intellect,” she said.
Among the awards presented were prizes recognizing excellence in visual and performing arts, world languages, humanities, mathematics, science, public speaking, leadership, and community engagement.
The final award of the afternoon, the Virginia Wing Outstanding Teacher Award, was presented to Mathematics Faculty Jessica Wang. Given annually to the teacher whose teaching skills, inspiration, and devotion have best served the student body in the Winsor tradition, the award is one of the celebration’s most meaningful honors.
Following the presentation, Senior Class Vice President Leela Uppaluri ’26 introduced History Faculty Michael Mirelman as the Class of 2026’s chosen speaker, describing his unique ability to build meaningful relationships with students both inside and outside the classroom.
“Mr. Mirelman has a way of making students feel seen,” she said. Whether through conversations in the hallway, class discussions, or enthusiastic responses to students’ latest interests and projects, he encourages connection and curiosity while helping students understand that “history is ultimately about the people.”
Drawing inspiration from the senior class theme, “Once Upon a Time,” Mr. Mirelman framed his remarks through three personal stories and three pieces of advice for the graduating class.
His first lesson, “don’t find your people,” grew out of his experience growing up feeling different from those around him. Rather than seeking comfort only among those who share similar backgrounds or interests, he encouraged students to embrace opportunities to be outsiders, arguing that some of life’s most meaningful learning happens when we step beyond familiar circles.
The second lesson, “drop your maps,” came from an ambitious bicycle trip he and his twin brother took from San Francisco to Portland. The journey succeeded not because of the maps they carried but because of the people they met along the way. The experience taught him the importance of curiosity, adaptability, and asking for help.
“Those paper maps taped to our handlebars were almost entirely useless,” he recalled. What ultimately guided the journey was the knowledge shared by fellow travelers and the willingness to remain open to unexpected experiences.
His final lesson, “dance foolishly,” drew on memories of one of his first Winsor assemblies, where students and faculty alike were invited to dance together on stage.
“I learned something about Winsor on that day that I have known ever since,” he said. “This school is a place where students can be themselves, celebrate vulnerability, stand on equal footing with their teachers, and obviously…dance.”
As he concluded, Mr. Mirelman returned to the three themes woven throughout his stories.
“Don’t find your people. Drop your maps—burn them even. And I hope that you dance foolishly for the rest of your lives,” he told the seniors. “Dance because your stories matter.”
Head of Lower School Sharon Jones Phinney closed the celebration by reflecting on the lessons embedded in Mr. Mirelman’s remarks.
“I hope we can all take Mr. Mirelman’s advice with us as we head into summer and toward our next adventures,” she said. “Look beyond our own circles, put down the map from time to time, and dance foolishly.”
Congratulating the award recipients, she noted that the students honored during the celebration have done exactly that—taken risks, embraced challenges, learned from one another, and strengthened the Winsor community through their talents, kindness, and spirit.
As the ceremony concluded, the community celebrated not only the achievements of individual award recipients, but also the collective accomplishments of a school year marked by intellectual curiosity, creativity, leadership, and connection.
