Reunion 2026: May 15–16

10 a.m.–7 p.m.
Alumni Welcome Center
Stop by for your nametag, weekend information, and refreshments.

11–2 p.m.
Dare to Be True: Celebrating the Class of 1976; Lunch and Program
Members of the Class of 1976 and guests are invited to a special luncheon with Milton leadership and the class program. There is no charge for this event for members of the Class of 1976 and their guests.

1–4 p.m.
Guided Campus Tours
Enjoy a guided tour of your favorite spots on campus, including newly renovated spaces. You’ll also hear about planned campus improvements. Tours run on the hour.
Reacquaint yourself with campus by using our panoramic virtual tour narrated by Milton students.

1–2:30 p.m.
Restorative Justice at Milton
Director of Restorative Practice Suzanne DeBuhr will introduce the principles and practices of restorative justice and its application at Milton, both as a foundation of healthy school culture and as a response in disciplinary matters. Ms. DeBuhr will share how restorative justice methods can shape a positive and supportive environment for students, staff, and the wider school community.

1–2:30 p.m.
Milton in the Classroom
Step back into the classroom during Reunion and experience the joy of learning at Milton. Classroom Sessions include:

• Exploring AI at Milton
• Conquering MegaBlunders at Last
• Hands-On STEM: Building Curiosity
• Alumni Sing

3-4:30 p.m.
Alumni Affinity/ Affiliation/ Club Gatherings
Reconnect with Milton’s vibrant community as alumni gather with current student groups for an afternoon of conversation and connection. Please stay tuned for more details on the specific groups attending. All alumni are welcome.

4:30-6 p.m.
Alumni Lounge
Stop by the Alumni Welcome Center to relax and recharge before the Class Dinners begin.

6–9 p.m.
Class Dinners
Connect with both old and new Milton friends at your class’s dinner. Enjoy a delightful dinner and the opportunity to celebrate with a glass of wine or beer. Please note that this event is for adults only.

The Classes of 1961, 1966, and 1971 will celebrate off campus; additional details will be shared by the class committees.  

8-9 p.m.
Wicked Sketchy
Check out Milton’s annual sketch-comedy performance “Wicked Sketchy.” The show, a community favorite, features hilarious, student-written sketches and is hosted by the Upper School Performing Arts Department.

9–11 p.m.
Milton Night Out
Enjoy a night out with fellow Milton young alumni and delicious snacks and drinks! Please note that this event is for 21+ alumni in the Classes of 2011–2021.

8 a.m.–7 p.m.
Alumni Welcome Center
Stop by for your nametag, weekend information, and refreshments.

9–9:45 a.m.
Memorial Service
A chance for alumni to come together to honor classmates who have passed.

10–3 p.m.
Meet the Milton Archivist
Meet Milton’s Archivist, Laura Pearle! Laura will share how Milton is preserving its rich history—from class traditions to the arts to athletic achievements—and you’ll get a behind-the-scenes look at the foundational work bringing Milton’s past to life.

10-11 a.m.
Milton Talks
Alumni will share their reflections on what Dare to be True means to them today.

11–3 p.m.
Guided Campus Tours
Enjoy a guided tour of your favorite spots on campus, including newly renovated spaces. You’ll also hear about planned campus improvements. Tours run on the hour.
Reacquaint yourself with campus by using our panoramic virtual tour narrated by Milton students.

11 a.m.–12 p.m.
School Leadership Symposium: Charting Our Course
Hear from Head of School Alixe Callen ’88 in conversation with Claire Hughes Johnson ’90 P ’24 ’27, President of the Milton Academy Board of Trustees. Together, they’ll share insights about Milton today—its direction, priorities, and the exciting work happening across campus to shape the school’s future.

11 a.m.–2 p.m.
Family Barbecue
Join us for a fun-filled afternoon at the Family Barbecue, featuring classic games, family-friendly activities, and a delicious barbecue lunch.

11:30 a.m.-12:30 p.m.
Lower and Middle School Open Hours
All are welcome to explore Milton’s Lower and Middle Schools during this special open house. Visitors can tour the spaces where Milton students learn and grow and see how these vibrant environments have evolved over time.

12:30- 1:30 p.m.
Milton Admissions Panel
Join members of Milton’s Admissions team for a panel discussion offering an inside look at the admissions experience across the Lower, Middle, and Upper Schools. Learn how Milton identifies and welcomes students who will thrive in its community, and hear about the values and vision that shape the school’s approach to building each new class.

1:30-3 p.m.
Nesto Gallery Reception – Go Figure Walter Horak ’66 and Dare to be Naive- Pictures and Play Tad Hills ’81
Nesto Gallery, Art and Media Center
Tad Hill’s ’81 exhibit in Nesto Gallery titled Dare to Be Naive: Pictures + Play offers a glimpse into children’s book author and illustrator Tad Hills’ creative process, tracing how his ideas move from rough sketches and text drafts to polished illustrations and finished text. The exhibition also features paintings and a collection of intricate cardboard Halloween costumes, all inspired by the “Dare to Be Naive” spirit of play and curiosity. Walter Horak’s ’66 exhibit ““Go Figure” out in front of the Art & Media Center works within a tradition that is several millennia old, and moved by a notion advanced by art critic Donald Kuspit, who proposed that sculpture was “metaphor making in three dimensions”. Horak’s intention is to extend the figurative tradition through metaphor: to compare human form to other aspects of experience and in so doing to express metaphysical ideas of balance, tension, and temporality. Sources of inspiration can be wildly diverse: calligraphy, modern dance, plant and landforms, and the work of other artists, ancient to contemporary.

2–3:30 p.m.
Class Blocks
Dedicated time for classes to come together and reconnect.

The Class of 1971 will gather off campus.

3-4:30 p.m.
Milton Athletic Games and Reception
Celebrate Milton’s athletic spirit with an afternoon of games and good company. Cheer on Milton teams as they compete on campus, then connect with fellow alumni, parents, and friends at a reception with Athletic Director Lamar Reddicks.

6–10 p.m.
All-Class Party
Connect with Milton friends, along with current and former faculty, at the All-Class Party—an evening of great company, food, and music. Enjoy a Taste of Boston buffet featuring local favorites, live music, and class-designated tables to make reconnecting easy. Please note that this event is for adults only.

The Class of 1971 will celebrate off campus; additional details will be shared by the class committee. The Class of 1966 will celebrate during their extended Class Block from 2-5 p.m.