Milton's list of notable alumni includes Nobel laureate T. S. Eliot, Attorney General Robert F. Kennedy, U.S.

Other founding members of the board of trustees included Fisher Ames, Nathanel Emmons, Thaddeus Mason Harris, Joseph McKean, and Ebenezer Thayer.

"[3] In March 1798, the Massachusetts legislature granted the academy a corporate charter and a state-funded endowment (three square miles of land in Maine).

[4] However, the academy did not actually open for business until 1807,[5] due to protracted disputes about whether the campus should be located in the center or outskirts of town.

[7] Alumni of the early academy include Major General Edwin Vose Sumner, who commanded Union troops at Antietam and Fredericksburg.

[11] From 1866 to 1884, Milton Academy survived as a paper entity, with a board of trustees but no teachers, students, or campus.

[21][22] Although Milton was nonsectarian, it traditionally educated large numbers of Unitarian students, in contrast to the many Protestant Episcopalian boarding schools founded at the turn of the 20th century.

[26] In 1901, several Milton friends and alumni (including William Forbes's son Cameron and Milton trustee Norwood Penrose Hallowell) helped establish Middlesex School, another formally nonsectarian prep school with a large and wealthy Unitarian clientele.

[23] Academic Richard Livingstone spoke at Milton's 150th anniversary celebration; his talk was published, in abridged form, in the November issue of The Atlantic Monthly.

[31] Other notable guest speakers include Scottish statesman John Buchan, the politicians Newton D. Baker and Franklin D. Roosevelt, and the diplomat Sumner Welles.

According to the New York Times, this made Milton "the first major American boarding school with a black headmaster.

The firm interviewed 60 alumni, parents, current and former staff and came to the conclusion that four former employees had engaged in illegal sexual conduct with students in the 1970s and 80s.

Following an appeal to the Massachusetts Supreme Judicial Court,[58] Buono pleaded guilty to two counts of rape of a child with force in 2022.

[59] In 2005, the school expelled five members of the boys' varsity ice hockey team for obtaining oral sex from a 15-year-old female student on three separate occasions.

[61] The DA dropped the charges against the three older students in exchange for an apology, 100 hours of community service, and two years of probation.