Littlefield was also a well-known wrestling coach at Mt. Vernon High School and Amherst College. Author John Irving served as an informal assistant coach at Amherst, and mentioned Littlefield in his essay-cum-memoir, "Trying to Save Piggy Sneed." On page 118, Irving wrote, “Henry Littlefield was the coach at Amherst then; Henry was a heavyweight—everything about him was grand. He was more than expansive, he was eloquent; he was better than good-humored, he was jolly. Henry was very rare, a kind of Renaissance man among wrestling coaches, and the atmosphere in the Amherst wrestling room was, to Henry’s credit, both aggressive and good-natured—a difficult combination to achieve.”
Littlefield received his B.A. from Columbia College, and his M.A. and Ph.D. from Columbia University.[6][7] During his studies, he also served as an officer in the Marine Corps from 1954 to 1958.[6] At Columbia, he played in the Varsity Show and attended the American Theatre Wing with the intention of becoming an actor.[6]