He sailed the New England coast, painting scenes from New Jersey to Maine, and once won the New York-to-Bermuda Race. His publications on navigation were standard text at the U.S. Naval Academy for many decades. Sheppard is also well known for his Venetian canal scenes. He studied abroad from 1888 to 1893, and also studied with well known American marine painter, M.F.H. DeHaas.
During his lifetime, he exhibited at: the Brooklyn Art Association (1874-81), the National Academy of Design (1880-99), the Pennsylvania Academy of Fine Art (1884), the St. Louis Expo (1904), and the Denver Expo, where he won a gold medal in 1884. Sheppard died in Greenwich, NJ in 1937.
In the collections of: the Albright Knox Art Gallery, the Nassau County Museum; the New Haven Colony Historical Society; the Museum of the City of New York, the Cumberland County Historical Society, the Mariner’s Museum, the U. S. Naval Academy, Washington University (St. Louis), the Springfield (MA) Public Library, the Mystic Seaport Museum, and the Peabody Museum (Salem, MA), among others.