Celebrating the Class of 2023

Tuesday June 6—The Class of 2023 bade farewell to their experiences on Pilgrim Road as students, faculty, and alumnae sent them off with caches of wisdom and good wishes at this year’s Commencement exercises.


Clouds and less than seasonal temperatures could not dim the positive energy that circulated throughout the ceremony. Advanced Rock On got the festivities started with a rollicking and uplifting rendition of Queen’s “Don’t Stop Me Now.” Seniors then processed into the courtyard, dressed in graduation-white garb of their choosing and holding a single red rose. 


“We’re here to honor the people that you have become, the people you have been all along,” said Head of School Sarah Pelmas, “but maybe you are just a little more focused and polished and clear about what you want from this world.” 


For an opening reading, students collectively chose a passage from Norton Juster’s 1961 children’s fantasy novel, The Phantom Tollbooth, about the humanity of mistakes and how normal it is to fumble in life. “You often learn more from being wrong for the right reasons than you do from being right for the wrong reasons,” Nicole Hwang ’23 read to the audience. 


As Allison Kaneb Pellegrino ’89, P ’21, ’22, president of Winsor’s Board of Trustees, next took to the lectern, she was still reflecting on Juster’s words and Hwang’s passionate delivery.


“Today I thought I was going to be rock-solid, but The Phantom Tollbooth — in Class III, we loved it so much that one of my classmates even named her son Milo. You girls always get me,” Pellegrino said.


“This is a happy and a sad day all at once as we say goodbye and good luck to you,” she added. “On this day you are graduating, you will no longer be enrolled students at Winsor, but at the very same moment you are becoming a part of something much, much greater.” 


Pellegrino reminded graduates that, as they move into new chapters in their lives, they also are now part of a 4,000-plus community of Winsor alums. “I am talking about a social and emotional [network] that spans continents, as well as decades.” 


Under the direction of Winsor Choral Director Andrew Marshall, all of the students rose to sing “Landslide,” a sentimental favorite by Fleetwood Mac about the passage of time that led some to reach for tissues. 


“To those of us of a certain generation, that is one of the most poignant songs you could have chosen,” Pelmas told the students as she, too, took a few breaths for composure.


In her speech to the graduates, Pelmas urged them to use all of their opportunities and everything they have learned for the power of good. 


“Whatever your contributions are within athletics, theater, the arts, medicine, community organizing, running a restaurant, or leading a nonprofit, we need you. The world needs to be inspired, uplifted, educated, and led. When we think about the vast disparities around the world … the world needs to be reminded of the worth of every single human being on this planet,” she said. 


Lindsay Whelan ’23 spoke on behalf of the Class of 2023, and she said her biggest takeaway from schooling is that “people make the place.” Whelan credited all of the levels of faculty, administrators, family, and students for making Commencement — as, indeed, all cherished Winsor events — such a memorable occasion.


“A once-empty tent, now filled with love, joy, and community,” said Whelan. “Just as all of these people made this place, this event, this day possible, you people, the Class of 2023 made this place and our time here so special.” 


Liz Friedman ’87 gave the Commencement speech to graduates and held nothing back, providing a realistic picture of the good, the bad, and the ugly moments that can span a career. A highly accomplished Hollywood writer who has written for such television shows as House, Orange is the New Black, and Xena, Friedman currently is the executive producer and co-showrunner for The Good Doctor.


Friedman shared experiences of successes and failures — and urged students to always remain curious and open-minded. 


“Living in the bubble is not what Winsor trained us to do, even if getting out of the bubble exposes us to views we did not see at Winsor. I ask you to embrace curiosity, to ask questions, and — this is really important — to listen to the answers. Create communities that are safe. That is very important. But not necessarily comfortable because, without challenges, I don’t believe there is promise,” Friedman said.


“I have had my share of challenges, and even firings. And you will, as well, but I hope less firings. Because even when you’re smart, well-educated and you do everything right, things don’t always go your way. And you will have a moment when you will need to choose between giving up and pressing on. What Winsor taught me was that giving up is not an option. Take a beat, rally yourself, tap into your community, and press on.” 


While this group of students spent much of their Upper School experience wearing masks and constrained by social distancing, the smiles on this day were now big and visible, and many graduates hugged faculty before leaving the stage with their diplomas. Roses were tossed into the air as graduates enthusiastically danced their way out of the courtyard to the upbeat 1980s-era anthem “Walking on Sunshine.” 


Congrats to the Class of 2023!

View the photo gallery.