NY 82 has been realigned twice between Pine Plains and Ancram since its assignment. The first realignment was made when the route was altered to bypass Gallatinville Road and continue on Silvernails Road to modern CR 7 in the hamlet of Silvernails. In the early 1950s, NY 82 was changed to exit Pine Plains to the east by way of an overlap with NY 199. At Hammertown, the two routes split and NY 82 continued north to Ancram by way of Ancramdale. Between Ancramdale and Ancram, NY 82 replaced New York State Route 201, a route from originally assigned as part of the 1930 renumbering. The sections of NY 201 from Ancram north to NY 22 at Copake and from Ancramdale south to NY 199 east of Pine Plains were given to the counties.