11 Sept. 1780–17 Sept. 1809
Dickinson organized instruction at the academy on two levels. In addition to the basic courses of reading, writing, arithmetic, geography, belles lettres, rhetoric, and English grammar, he offered such advanced studies as Latin, Greek, Hebrew, French, Italian, algebra, trigonometry, geometry, metaphysics, surveying, navigation, and astronomy. An average of between seventy and ninety students attended the academy during his tenure as preceptor. Perhaps because of his success, David H. Mayhew, a graduate of Williams College, was secured in 1807 to assist Dickinson.
Academia did not monopolize Dickinson's time, however; he read law under Alexander Falconer, who lived about nine miles north of Louisburg in an area known as the Glebe. He also was a competent businessman. Although he arrived in Louisburg with few possessions, by 1809 he had acquired an estate valued at between $6,000 and $10,000. This was accumulated through land ownership, participation in the trade of enslaved people, and by profitable money lending.
In 1808 Dickinson resigned his position at the academy to begin a career in law. He practiced briefly in Louisburg and Franklin County, but died the following year as a result of "bilious fever" contracted during a trip to the eastern part of the state. He never married. He was buried in a family cemetery eight miles north of Louisburg near what is today U.S. Highway 401.