Born in Buffalo, New York, Cheffetz would later move with his family to Massachusetts at the age of five. He studied under Philip Hale at the School of the Museum of Fine Arts and later attended the National Academy of Design in New York where he studied with William Auerbach Levy.

In the late 1920s, Cheffetz began his love affair with wood engraving. He spent much of his life engraving the landscape of his beloved New England. In 1984, the Springfield Museum of Fine Arts mounted a solo exhibition of the artist's work. He was elected to full membership in the National Academy of Design in 1944.