Defining Community and Excellence: Ms. Sugrue’s Journey at Milton

By Emlyn Joseph ’27

As the 2025-2026 academic year wraps up, one naturally turns to the next year and begins wondering what it holds. The 2026-2027 academic year will have numerous changes, from departmental shifts to new students. One change stands out to our community: the departure of our Academic Dean Ms. Heather Sugrue, who has left a notable mark on Milton Academy. From a dorm parent and House Head of Hallowell House to a math teacher and the Academic Dean, Ms. Sugrue has worked at all of the facets of Milton life, connecting with students and faculty and leaving a lasting impact for the future of this institution.

Before coming to Milton, Ms. Sugrue taught at St. Paul’s School in New Hampshire. Many of her colleagues there “had raved about Milton”; after getting her masters degree, she applied to places around the greater Boston area and chose to come here. Since 2001, Ms. Sugrue has been an invaluable member of our community. During her first years at Milton, she lived in Hallowell House and worked in the math department. She remarks that not only has “the math department certainly bounced around campus” but also residential life and general student culture has also shifted. For example, events like the dorm open house or baccalaureate hold special memories for Ms. Sugrue. However, many aspects of Milton have still remained the same for her: “The student body has always been this great group of people with differing interests and different energies from all over.” She expresses that her work across campus has been valuable through the “learning and growing [she has] done as an educator, through the math department and through senior colleagues.” Moreover, raising her children on campus and living with her family have brought in unforgettable memories and growth. These different experiences across Milton have allowed Ms. Sugrue to integrate new ways of teaching. Indeed, she reflects something crucial she “found [herself] leaning into as a teacher over time is just really focusing on building relationships with students.”

As the academic dean since 2019, Ms. Sugrue has naturally continued to be at the forefront of the Milton student experience both in and outside the classroom. Indeed, Milton’s annual sketch comedy show, Wicked Sketchy, has featured Ms. Sugrue several times. Mr. Parisi from the Performing Arts Department explains that students entirely write these sketches, and since 2022, curated sketches have centered around the academic experience; inevitably, Ms. Sugrue makes an appearance.

When reflecting on her time as Academic Dean, Ms. Sugrue acknowledges a key challenge: the Covid-19 pandemic. “I would say the hardest time was COVID…within this office, we were trying to make schedules that would work across the world,” she explains, as the faculty body navigated rapid changes to continue to make a Milton education accessible. Working through such challenges, Ms. Sugrue has strengthened both her leadership and the community of Milton itself.

The next chapter of her life will be situated around Cape Cod. Her older son Brady Sugrue ’26 will be going to college, and her younger one Aidan Sugrue ’28 plans to study abroad in Spain. She reflects, “it is not hard to imagine being somewhere else; it is hard to imagine not being here.” That being said, she emphasizes the importance of appreciating the campus and the institution: “I appreciate it… it is beautiful. And so occasionally you need that sort of reminder to open your eyes wider.” Looking forward, she “is excited to see what the rest of this year brings and where [she] might head.”

For all students, particularly seniors as they begin a new journey beyond Milton, Ms. Sugrue underscores how important cherishing friendships and relationships is. In addition to that, remember that stressful moments do occur, “but when you step back…on the whole, life is okay.” Staying optimistic throughout life is essential, she adds on. Ultimately, one of the most rewarding parts of her career has been “tied to students…whether it be advisees or other students that I have been able to get to know better…it is always a pleasure to keep up that – those points of connection.” These values of connection and positivity are the essence of what Ms. Sugrue has instilled in students, faculty, and other community members of this institution. Truly, Ms. Sugrue’s teaching and work has inspired countless members of our community and left unforgettable impacts on every one of us. On behalf of the entire Milton community, we thank you, Ms. Sugrue, and we wish you all the best.