North of the split with US 44, NY 82 passes through the former hamlet of Bloomvale. It then leaves the vicinity of the parkway and begins to parallel Wappinger Creek as it heads through the northern extent of Dutchess County. At Pine Plains, the creek terminates while NY 82 intersects NY 199 in the center of the hamlet. NY 82 turns east, forming a brief overlap with NY 199 before splitting outside of the community. Shortly after leaving NY 199, NY 82 passes into Columbia County.