NY 82 begins at an intersection with NY 52 in Brinckerhoff. The route proceeds to the northeast, paralleling the path of the Fishkill Creek through southern Dutchess County. At the East Fishkill hamlet of Hopewell Junction, NY 82 briefly overlaps NY 376 before separating from the waterway east of the hamlet. 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. To the north in Billings, NY 82 intersects NY 55 before continuing onward toward the village of Millbrook. South of Millbrook, NY 82 turns to the west at an intersection with NY 343. Midway between Millbrook and the Taconic Parkway, NY 82 meets U.S. Route 44 and overlaps the route for a short distance to the west. The two routes separate just east of where US 44 meets the parkway.