[2] Dickinson studied with George Bridgman and William Merritt Chase at the Art Students League of New York from 1910 to 1911, and from 1910 to 1912 he was a pupil of Douglas Volk at the school of the National Academy of Design.
[1] He spent time traveling around the country doing manual labor, working in lumber camps and finding employment as a surveyor's roadman and farmhand.
[3] Dickinson was active as an instructor for many years, teaching at the Art Students League in 1919–1920 and heading a life class at the National Academy from 1928 to 1931 and again from 1939 to 1943.
A self-portrait is part of the Academy's permanent collection, as are portraits of Mary Gray, George Wharton Edwards, Harry Wilson Watrous, Georg J. Lober, Frederick K. Detwiller, Donald De Lue, Ernest Nathaniel Townsend, John Carroll, Theodore E. Blake, Otto R. Eggers, Robert S. Hutchins, Bryant Baker, and Edgar I.
[16] Dickinson also painted many figurative works throughout his career; a number of these were born of his experiences in Alabama, and are owned by the Greenville County Museum of Art in South Carolina.