Aside from Saturday morning classes at the Cleveland School of Art, Stroup was a self-taught artist. He spent most of his adult life as a magazine editor, first at Town & Country, then at House and Garden, and began to draw only after moving to Nantucket. Working initially in felt-tipped pen, Stroup depicted the flat Nantucket landscape, but turned to watercolor after his first exhibition. Stroup began working in oil in 1976. He exhibited at the Main Street Gallery.