NY 42's northern segment proceeds northwest through the hamlet of Shandaken as a two-lane residential street, intersecting with the northern terminus of CR 47 (Creek Side Drive) at the shore of Esopus Creek. After CR 47, NY 42 passes south of Glen Brook Park, continuing northwest through the hamlet as a two-lane residential road. Before crossing under some power lines, NY 42 bends northeast, intersecting with Ford Road, where it turns northwest once again, paralleling the power lines. During this northwestern stretch alongside Halcott Mountain, NY 42 intersects with a former alignment of itself, which parallels to the west for a short distance. The route soon enters the hamlet of Bushnellville, where it becomes a two-lane residential street. Just after the intersection with Gooding Road, NY 42 bends northeast and crosses the county line into Greene County.