[2] Cummings was born in St. Albans, Vermont, educated at the Hoosac School in New York, studied American art and architectural history at Oberlin College, and received his doctoral degree from Ohio State University in 1950.
When young, he spent winters with his parents in Bennington, Vermont, and summers with his grandmother in Southington, Connecticut.
Elmer D. Keith, a Wallingford, Connecticut, antiquarian, author and collector, taught Cummings to deconstruct a building to look behind its repairs and later additions.
In graduate school, Cumming's thesis was on seventeenth-century Massachusetts buildings, and his dissertation was on the Federal architect Asher Benjamin.
In 1951, as colleges began cutting staff due to the Korean War, Cummings lost his academic post and reluctantly became an assistant curator in the American Wing at New York's Metropolitan Museum of Art.