Dickinson was born and raised in Seneca Falls, New York, in the Finger Lakes area; his family moved to Buffalo in 1897. The death of his mother from tuberculosis in 1903, the suicide in 1913 of his older brother, Burgess, his father's remarriage in 1914 to a much younger woman, and the death of a close friend in combat have all been cited as influences on the themes of his later work. As a boy Dickinson had assumed he would become a minister, like his father, but his brother's suggestion of a career in the navy proved more to his liking. Unfortunately, he failed the entrance exam of the U.S. Naval Academy twice. In 1911 he enrolled at the Art Students League, where he studied under William Merritt Chase. In the summers of 1912 and 1913 he stayed in Provincetown, Massachusetts, where he studied with Charles W. Hawthorne, and continued there year round from 1913 to the summer of 1916, working as Hawthorne's assistant in 1914. From late summer 1916 through year's end Dickinson investigated the possibilities of printmaking in Provincetown with fellow painter Ross Moffett, and made further attempts in the '20s and '30s, but felt his time was better spent painting.
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