New York State Route 82

In 1908, the New York State Legislature created Route 1, an unsigned legislative route extending from New York City to Rensselaer. Route 1 left modern NY 22 at the hamlet of Amenia and followed what is now U.S. Route 44 west to Smithfield Valley Road. From there, the route headed north through the town of North East and northwest through the town of Pine Plains to the community of Pine Plains by way of Smithfield Valley Road. Route 1 continued northward on Silvernails and Gallatinville Roads and modern CR 7 to the hamlet of Ancram, where it turned northeast to follow today's CR 7 toward Copake.[4][5] On March 1, 1921, Route 1 was realigned between Amenia and Copake to use modern NY 22 instead.[6]

NY 82's northern terminus at US 9, NY 23 and NY 9H in Bell Pond.

In the 1930 renumbering of state highways in New York, the portion of pre-1921 legislative Route 1 between Pine Plains and Ancram became part of NY 82, a new route extending from the vicinity of the village of Fishkill in the south to the town of Livingston in the north.[2][7] At the same time, the segment of old Route 1 from Amenia to Pine Plains became part of NY 82A, an alternate route of NY 82 between the hamlets of South Millbrook and Pine Plains by way of Amenia.[2]

The portions of NY 82 and NY 82A between Washington's Hollow and Amenia were incorporated into the new US 44 c. 1935. As a result, NY 82A was truncated to begin at US 44 near Amenia while NY 82 overlapped US 44 from South Millbrook to Washington's Hollow.[8][9] The routings of NY 82 and NY 82A between South Millbrook and Pine Plains were swapped c. 1936, with the route via Amenia becoming NY 82 and the route via Stanford becoming NY 82A. From South Millbrook to Amenia, NY 82 overlapped US 44.[9][10]

NY 82 has been realigned twice between Pine Plains and Ancram since its assignment. The first realignment was made c. 1935 when the route was altered to bypass Gallatinville Road and continue on Silvernails Road to modern CR 7 in the hamlet of Silvernails.[8][9] 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,[11][12] a route from originally assigned as part of the 1930 renumbering.[7] 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.

In 1966, NY 82 and NY 82A were restored to their c. 1935 alignments, with NY 82 routed through Washington's Hollow and NY 82A beginning in Amenia.[13] On April 1, 1980, ownership and maintenance of NY 82A was transferred from the state of New York to Dutchess County as part of a highway maintenance swap between the two levels of government. Also transferred from the state to the county was the portion of NY 82's original routing in Pine Plains between NY 199 and Silvernails Road.[14] Following the swap, NY 82A was redesignated as CR 83 while NY 82's former routing in Pine Plains became CR 83A.[15]

As part of the above highway maintenance swap, the state assumed maintenance of the portion of NY 82 from NY 199 to the Columbia County line. At the same time, the state also acquired ownership of the segment of NY 82 in Columbia County between the Dutchess County line and CR 7 in Ancram as part of a separate swap with Columbia County. Both segments had previously been county-maintained.[14]

NY 82 originally entered the hamlet of South Millbrook instead of bypassing it to the west. Its former routing into the community is now CR 111 and known as "Old Route 82".[16]