Alumni Reunion Bonds Milton Students Past and Present

By Nini Lu ’29

Milton Academy’s alumni reunion weekend kicked off on May 15, 2026. For the first time in years since COVID, this event was held during the academic year instead of during the summer. Through club gatherings on Friday afternoon, alumni met current students, reconnecting with Milton’s culture and seeing its progression. There was a diverse range of topics, with student club leaders present from different orginizations, including the Measure and the Paper, Public Issues Board, and Speech and Debate.

Speech and Debate’s alumni meeting took place in the Kellner Performing Arts Center. Compared to the other events, this one had great attendance, and even many of those who hadn’t participated in debate in their Milton days were glad to learn about it and chat about other topics. The alumni were very enthusiastic, “eager to hear about [the students’] experiences and relate them to their own,” as observed by Jiner Huang ’28. For her, it was “incredible to see all these people come together across their different experiences… united at this one place.”

The affinity group reunion began in Thacher Auditorium, with food, tables, and tags set up for the culture clubs that hosted their events there. However, a lot more students and faculty showed up than alumni, with around twelve student leaders, five of whom were around a single table, often all talking to only a single alum. One of these conversations was with an alumna who was one of the first recipients of a scholarship from Hong Kong. As one of only two Asian students in her year, she remembered there being only one culture club for all students of color. Riley Qiu ’28, a board member for Tang, the Chinese culture club, recalled that the alumna’s experience was fascinating to hear about, especially because so much has changed within the four decades. With around a third of the current student population identifying as Asian, it was heartwarming for the alumna to see that Milton now has multiple groups, including Asian Society, Tang, Hallyu, the Korean culture club, and SAMENA, which includes South Asian identities, that celebrate diverse Asian identities.

Later, on Saturday, alumni cheered on the varsity baseball team as they defeated Tabor Academy, claiming the seat of Independent School League champions. Furthermore, alumni bonded through a family barbecue over lunch, where they were welcome to bring their children, too. Henrik Brun ’91, who attended both events, as well as a cocktail party, found the series of events to be a “really nice alumni gathering with classmates from all over the country coming back,” and believed that our head of school, Dr. Alixe Callen ’88, “is charting a great course forward for the school.”

Moreover, Robbins and Wolcott hosted tours on Saturday between 11 AM and 3 PM. The visitors, many of who were former residents of Robbins and found it wonderful to return, shared positive reactions. The majority of day student alumni, though, had never set foot in a dorm before. Siri Chadalawada ’26, a guide for the alumni’s dorm visitations of Robbins House, noticed that there had evidently been a great divide between boarding and day students, especially throughout the ’60s, ’70s, and early ’80s. She remarked that, according to an alumnus, many “social cliques” existed, where interaction between different groups was very limited.

Furthermore, “the cultural dynamics were very different back then.” Although divisions within the student body have generally subsided, it is still empirical that the current boarder-day divide is growing once more: in the Milton Paper’s annual State of the Acad survey, 70.6% of 2026 respondents believe that such a divide exists, an increase of 17.1% compared to two years ago.

Overall, this special reunion allowed for Milton students, both past and present, to bond over shared experiences while reflecting on what is unique to each of us. As Ms. DeGregorio stated, “many alumni shared with the Advancement team during the weekend how much it meant to them to be here with our students.” Indeed, with more than 650 alumni attending, and well over $500,000 raised for the school, this year’s reunion was an outstanding success from all metrics. Most importantly, the connection between Milton students from all classes is “a powerful reminder of the transformative impact Milton has had on their lives, and the importance of the lifelong relationships that came from their time here,” said Ms. DeGregorio.