Pinkerton Academy is a private, non-profit corporation administered by a headmaster who acts under the direction of an elected board of trustees.

[8] In 1793, a classical high school was established in the eastern part of Londonderry (split off in 1827 as the town of Derry) and was maintained for twenty years by direct tax, tuition, and voluntary contributions.

The academy opened on December 4, 1815, as an all-male institution with an endowment of $16,000 by John Pinkerton "for the purpose of promoting piety and virtue and the education of youth in science, languages, and the liberal arts.

[10] In 1881, upon the death of John Morrison Pinkerton, son of Elder James, the academy received a second bequest.

In 1949, the academy entered into an agreement with the town of Derry that marked a significant turning point in the school's history.

As a result of the service agreement, Pinkerton educated all high school aged students who lived in Derry.

Over the next thirty years, additional communities (Chester, Hampstead, Auburn, Londonderry and Windham) signed service contracts with the academy.

In response to the increased number of public school students attending Pinkerton, new facilities were built.

Due to the changing needs and interests of this larger student population, Pinkerton once again developed new courses and fields of study while maintaining its existing college preparatory programs.

The center of the academy's campus holds buildings where classes are taught, and the surrounding area is used for specific non-academic purposes.

[16] Some buildings are dedicated to important people of the academy, such as Robert Frost, Alan Shepard, and Ivah A. Hackler.

[18] Pinkerton offers a variety of 28 sports throughout the school year including football, field hockey, cheerleading, golf, cross-country and soccer in the fall; basketball, gymnastics, ice hockey, track, swimming, alpine ski racing and wrestling in the winter; baseball, volleyball, softball, lacrosse, tennis, and track in the spring.

[19] The teams are named the Astros in honor of astronaut and Pinkerton alumnus Alan Shepard, the first American in space.

In September 2013, the Pinkerton Academy football team played its first ever home night game under the newly installed stadium lights.

More recently, "The Long Red Line", as the team is called, ranked as high as 23rd in the nation in 2009, and won the state title four years in a row in 2013, 2014, 2015, and 2016.

In their final competition year before being dissolved, the team won the 1992 intercollegiate championship, held at Dartmouth College.

[23] The school also had a Chinese exchange program, where students would raise money to stay at Tianjin with a host family and attend classes in English there.