NY 82 was assigned as part of the 1930 renumbering of state highways in New York. An alternate route of NY 82 from South Millbrook to Pine Plains, designated as New York State Route 82A, was assigned at the same time. Part of NY 82A was replaced by the new U.S. Route 44 . The routings of NY 82 and NY 82A were swapped in the mid-1930s, but the change was reverted in 1966. Ownership and maintenance of NY 82A was transferred from the state of New York to Dutchess County in 1980, at which time it was redesignated as County Route 83 (CR 83).