In 1866, the town of Milton decided to establish a public high school, causing Milton Academy to temporarily suspend its operation and to lease its building to the town. In 1885, however, the Academy became active again, thanks mostly to the largesse of businessman John Murray Forbes’s support of the endowment, this time moving its location to the corner of Randolph Avenue and Centre Street in a building which would later come to be named Warren Hall.  Although Forbes would be known as the “Founder of the Reestablished Academy,” his son William Hathaway Forbes was chosen the new President of the Board of Trustees. Milton’s population having increased from 1,039 in 1798 to 3,555, the Academy was able to enroll 40 boys and girls and employ four teachers under the leadership of Principal Samuel Thurber.

Recruited by trustee Harriet Ware, Harrison Otis Apthorp became Headmaster in 1887, serving till his retirement in 1904. During his tenure the Academy expanded significantly in population and physical size, enrollment growing to 135 and several new buildings rising on campus, including three boys’ boarding houses, Forbes, Robbins, and Wolcott, a gymnasium, and Wigglesworth Hall, a second schoolhouse constructed next to Warren Hall along Centre Street. In 1898, the school’s centennial year, Apthorp created the school shield and motto “Dare to be True,” which he adopted from a poem attributed to the poet George Herbert.

In 1901, the trustees divided the Academy into separate Boys’ and Girls’ Upper Schools, the Lower School up to Grade 6 remaining coeducational. Soon, Hathaway House, a dormitory for female boarders, was erected as was Ware Hall, a girls’ schoolhouse, directly across Centre Street from Warren and Wigglesworth. For most of the next 70 years, the three schools prospered under one Board of Trustees and Headmaster, who also acted as the Principal of the Boys’ School while the Girls’ and Lower Schools had their own Principals. The Apthorp Chapel and the Robert Saltonstall Gym were added in 1921, and the old gym was renovated and moved across the street to serve the girls on their campus. Although many faculty and older students left to serve their country during the two World Wars, the school carried on, even educating 40 children tuition free, who had been sent to the states from war torn England in the 1940s.

In the 1970s and 80s under the leadership of Headmaster Jerome Pieh, the upper schools gradually merged over a period of 15 years into one coeducational entity.  At the same time, the Academy broadened its outreach, diversifying its student body and becoming a truly international school and multicultural community attracting students and faculty from different races and backgrounds. Edwin Fredie, formerly principal of Needham High School, became Milton’s first African American Headmaster in 1991, following Pieh’s retirement, leading the school’s bicentennial celebration in 1998.  Robin Robertson, the first female Head of School, took Milton into the 21st century, and Alixe Callen, a 1988 graduate with wide experience leading both independent and public schools, became the second female Head of School after her election in 2023, following the retirement of Todd Bland, who had resolutely guided the school through the painful  Covid pandemic toward the end of his 14 year tenure..

Though the enrollment has grown from 135 to 1034 and the modern 125-acre campus, with its state-of-the-art facilities in the arts. sciences, and athletics, looks far different than it did 125 years ago, the Academy’s trustees, administrators, and faculty hold fast to their mission of educating the whole person of each student in their care to “Dare to be True.”

Bibliographical source: Visions & Revisions, A Pictorial History of Milton Academy, copyright 1995 by The Trustees of Milton Academy