[1] Founded in 1876 by William M. Pingry, Vermont Academy originally included a boys-only lower school, which gave "...special attention to life in the open.

It is fundamentally and inseparably a part of Vermont — Vermont hills and valleys; it is Mountain Day with the trees a riot of color and the steaks sizzling over the coals; it is ski tracks making patterns on smooth hillsides; it is the lovely blue pyramid of Mount Ascutney rising over the foothills; it is spring nights at the cabin and the first swimming at Bowles pond.

The Vermont Academy curriculum includes courses in Art, College Counseling, English, History, Learning Skills, Mathematics, Music, Science, and World Language (French, Latin, or Spanish).

Fall athletics include: crew, cross country, equestrian, mountain biking, soccer, and wilderness skills.

Spring athletics include: baseball, equestrian, fly fishing, golf, lacrosse, rock climbing, and tennis.

[7] The Vermont Academy campus is located on the north side of Saxtons River, bounded on the south by Burk Hill Road and on the east by Pleasant Street.

[9] Vermont Academy has educated numerous American politicians and military officers, including the diplomat John Barrett (1885), the ambassador Mark Palmer (1959), the judges Joseph Bogdanski (1931), Fred Tarbell Field (1895), and Frank L. Fish, and three members of the House of Representatives: Henry L. Bowles, Howard A. Coffin, and Samuel B. Pettengill (1904).

Professional basketball players include: Bruce Brown (2016), Keron DeShields (2011), Corey Johnson (2015), Tyrique Jones (2016), Jordan Nwora (2017), Simisola Shittu (2018), and Christian Vital, who later transferred to St. Thomas More School.

Other notable athletes include Bert Abbey (1887) and Danny MacFayden of Major League Baseball, the skiers Rob DesLauriers (1983) and Joseph Peter Wilson, the football player Marcus Santos-Silva (2017), and Jim MacLaren (1981), a triathlete.

The authors George Burwell Utley, Mark W. Smith (1987), John Steptoe, and Helen M. Winslow, the orthodontist Albert H. Ketcham, the scientist Florence R. Sabin (1889), and the religious figures Bishop John Bryson Chane (1963) and missionary Clara Converse (1879), who is credited with establishing education for women in Japan, all graduated from the school.