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Established in 1791 to comply with a Massachusetts law requiring the District of Maine to provide public education, Berwick Academy is Maine’s oldest academy. The original 10-acre lot, donated by a local judge, was one-half mile from the village of South Berwick. Originally a school for boys, girls were admitted 37 years later which led to the need for a new, larger building. Additional structures and associated landscape features were added over time, culminating in the current quadrangle arrangement on the present-day 72-acre campus.

Although there are many landscapes in Maine with Frederick Law Olmsted, Sr. and Olmsted firm associations, Berwick Academy is one of a small number of sites designed during the Olmsted, Olmsted & Eliot tenure. In 1894 the William Fogg family hired the firm to design the grounds of the newly-constructed Fogg Memorial Building. The plan included a stone retaining wall and hillside lawn, pedestrian paths and steps, and a horseshoe-shaped carriage driveway. The plan was implemented but adapted over time. Some original features remain, including the roadside stone retaining wall and the location of paths. Other elements, such as the stone entrance path and steps, were restored in the 1990s. The Academy was listed on the National Register of Historic Places in 1978 and is included with the 1996 Berwick Academy Historic District Boundary Increase.