Born in Toronto, Ontario, Sheppard studied at the Central Ontario School of Art in Toronto as well as under mentors such as George Reid, J.W. Beatty and William Cruikshank at the Ontario College of Art, Toronto in 1912. He also did an apprenticeship as a commercial engraver with Rolph, Clark and Stone in Toronto. Sheppard worked in oil, watercolour and pencil with subjects including landscapes, rivers and lakes, streetscapes, portraits and figures. He also painted in New Brunswick, Nova Scotia, and in Quebec. Most of his career he worked as a commercial lithographer and exhibited his works with the RCA in 1915-1954 as well as the AAM, MMFA in 1916-1950. His work is in the collections of the AGO, CWM and NGC.