Born in Toronto on October 21, 1882, Sheppard received his art training at the Central Ontario School of Art and Design and the Ontario College of Art under George Reid, John William Beatty, and William Cruickshank, accomplished artists and influential teachers. There in 1912-13 he won the Sir Edmund Walker Scholarship and later the Stone Scholarship (Life Classes) in 1913-14, as well as nine Honours diplomas for painting, drawing, and composition. Earlier in his youth Sheppard served apprenticeships in the commercial engraving houses of Toronto such as Rolph, Clark, Stone Ltd. His superb skills as a lithographer provided him the means of a livelihood throughout his life that was wholly and tirelessly devoted to art. After 1912 he travelled extensively throughout Europe and the United States. He was elected a member of the Ontario Society of Artists in 1918 and an Associate of the Royal Canadian Academy in 1929.