On Friday, May 15, and Saturday, May 16, as Milton students attended classes, 620 alumni, from graduation classes every five years before 2021 (e.g., 2016, 1991), arrived on campus for Reunion Weekend, marking the first time in fifteen years that the event has taken place during the school year.
Development Events Manager Kathleen Pendleton said the change in timing came partly from logistical constraints and partly from a desire to create more meaningful interaction between alumni and students. “The World Cup was going to be the same weekend as the reunion, so we decided to move it to May,” Pendleton said. She added that Head of School Alixe Callen, who had seen reunions held during the academic year at previous schools, “really wanted to see what it would be like.”
The coordination required to pull off a reunion with classes in session was complex. Advancement Events Coordinator Sarah Kennedy said that, for a full year, the Development Office worked with faculty, facilities, admissions, and students to coordinate 30 events across the two-day reunion. “We had to make sure that [we] don’t use the room when there’s a class going on, or we have to make sure we move the tent away from the dorms... we don’t want to be super loud all night. It was a tremendous amount of planning.”
Students were woven into the weekend’s programming. Development Ambassadors, who work with the office throughout the year, greeted alumni, ran check-ins, offered tours, and participated in panels. Alumni joined classroom and club events, including AI programming, a Megablunders session, and gatherings with publications and affinity groups. Students from the Public Issues Board, Speech and Debate, The Milton Measure, and The Milton Paper also spoke to alumni.
Development Ambassador Molly O’Brien ’26 reported that alumni, particularly those who attended before Milton became fully co-educational, were intrigued and surprised by how much the campus has changed. O’Brien, who toured a group of men from the Class of 1966, said the alumni “were shocked to figure out that [Robbins] was now a girls’ dorm.”
Many alumni enjoyed reconnecting with former classmates. Adam Bookbinder ’86 complimented how his class saw “the highest number of people coming back of any class for quite a while.” He said, “The fact that we had 60 people show up 40 years later is pretty amazing.” This year, at her 35th reunion, Amy Hamill ’91 noticed a different tone in her conversations with classmates at prior reunions. She appreciated “people almost expressing their vulnerability or challenges that people at our age–ages 52 and 53 years old–may have had… People aren’t trying to impress each other, they’re really just trying to appreciate and enjoy one another.”
Sander Cohan ’96 enjoyed the class dinner and all-school party. “It was really great having fun at the all-school party with everybody,” Cohan said. He felt that “it was great to spend some time and hang out on the campus,” and appreciated that he got “to see all sorts of folks from not just your class, but across the [different classes].” Bookbinder further echoed that the class dinner in Straus was a particular success: “People stayed for more than three hours.”
An emotional moment came when alumni received letters they had written to themselves as seniors. “The class of 2016 wasn’t able to get their letters at their last reunion because of Covid, so they [did] this year, at their 10th reunion,” Pendleton said. “It was really fun to see everyone’s reaction to some remembering that they wrote [a letter], some not remembering that they wrote a letter.”
A highlight for Pendleton was watching the “four alumni who recreated the photo from their yearbook together down to the Burger King crowns that they wore,” remarking it as a “really lovely moment.”
The weekend also served a fundraising purpose. “Each class [had] their own fundraising goal for both dollars and participation for reunion,” Pendleton explained, “It was a philanthropic opportunity for our alumni.” Rosheen Kavanagh, development office staff, quantified the total funds raised so far by reunion donations as $561,482. However, Kennedy reiterated the weekend’s larger goal to keep alumni connected in whatever way felt most meaningful to them: “We want them to come back and remember Milton well…and see the way that it’s growing and still shaping people.”
The weekend offered a moment to reflect on where time had taken them. Hamill recalled a memory from her senior year, when her science teacher played a James Taylor record for the class and simply smiled at them from a stool as the song filled the room. The moment felt silly at the time, she reflected, but has stayed with her ever since. “I sort of think that if you choose to come back to reunion, hopefully that’s an indication that you are a little bit in touch with what James Taylor had to say about enjoying the passage of time… It [was] an opportunity to connect with really interesting people and just appreciate people’s trajectory of life.”