The New Hampshire Register of 1810 listed the Chesterfield Academy as one of only 12 academies in the state.
Academies — private secondary educational institutions — were virtually the only means of obtaining a secondary education in New Hampshire at the time. Public schooling went to the eighth-grade level. Students who wanted to continue their education beyond that level were responsible for paying for it themselves.
The Chesterfield Academy had actually been founded in 1790 and was the first academy in southwest New Hampshire. It had an excellent reputation during its early years, being ranked second only to Phillips Exeter.
Between 70 and 100 students were generally in attendance. Most of these were local residents, but many others came from Vermont and Massachusetts. The bylaws of 1806 set rules and regulations for the academy. Tuition cost 25 cents per week, and unexcused absences were to be punished by a 25-cent fine for each day absent.
Students were forbidden to use indecent language, to keep cards or dice, or to visit public houses. They were also to keep themselves neat and clean and were not to dispute or contradict the principal.
Many students went on to distinguished careers after their stay at Chesterfield, including several who became prominent lawyers and doctors. Some of the more famous graduates included Rev. Hosea Ballou, pioneer of Universalism; Dr. Horace Wells, inventor and pioneer in the field of anesthesia; famed surgeon Amos Twitchell; and Gov. William Hale.
The school realized its greatest prosperity during the 1820s, when Chesterfield was one of the leading towns in the county with two hotels, six stores and a population greater than that of the county seat at Keene.
Public high schools began to predominate in the middle of the 19th century, however, and academies began to lose their importance. The Chesterfield Academy continued on for many years, but after 1850 it lost the previous prominence that had made it one of the most distinguished educational institutions in New Hampshire.