The route proceeds to the northeast, paralleling the path of the Fishkill Creek through southern Dutchess County.

NY 82 continues north to the community of Arthursburg, where it meets the Taconic State Parkway at an interchange.

Past the exit, the two roads begin to follow parallel routings through the center of the county.

It then leaves the vicinity of the parkway and begins to parallel Wappinger Creek as it heads through the northern extent of Dutchess County.

From the county line northward, NY 82 passes through Ancramdale and Ancram prior to meeting the Taconic Parkway a second time near the Lake Taghkanic State Park in West Taghkanic.

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.

[6] 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.

At Hammertown, the two routes split and NY 82 continued north to Ancram by way of Ancramdale.

[14] NY 82 originally entered the hamlet of South Millbrook instead of bypassing it to the west.