Kents Hill was founded in 1824 as the Maine Wesleyan Seminary[3] by Luther Sampson, a Duxbury, Massachusetts native and a veteran of the American Revolution.

According to an early publication of the Kents Hill Breeze, a defunct school periodical, Luther "was of the fifth generation in lineal descent from Henry Sampson, one of the Pilgrim band that landed on Plymouth Rock, December 22, 1620.

Sampson, his wife Abigail Ford, and their children lived in Duxbury and, later, Marshfield, before relocating to over two hundred acres in Readfield, Maine, around the turn of the century.

[4] In 1821, Sampson incorporated there the "Readfield Religious and Charitable Society", whose original charter contained no mention of a school, but rather laid a plan to support area Methodist belief and practice.

Failing financially and seeking a more efficacious means of performing his mission, by 1823 Sampson had begun to explore the possibility of changing the society's identity into one rooted in the education of youths.

Francis H. Fassett, Maine's leading architect in the middle of the 19th century and an important figure in the rebuilding of Portland after the 1886 fire, designed Bearce and Ricker halls.

[14] In 2007, social studies teacher, David Pearson, was awarded a Harvard Singer Prize for Excellence in Secondary School Teaching.