Route Description
NY 199's western terminus is at a cloverleaf interchange with US 9W in the town of Ulster, situated just north of the city of Kingston and south of the hamlet of Lake Katrine. US 209 ends here and becomes NY 199. The portion of US 209 near Kingston is a four-lane limited-access highway, and the first mile (1.6 km) of NY 199 serves as a continuation of the expressway. NY 199 has one interchange with NY 32 before narrowing to two lanes as it approaches the Hudson River. The route crosses the river by way of the Kingston–Rhinecliff Bridge, a two-lane toll bridge linking the towns of Ulster and Rhinebeck.
Now on the eastern bank of the river, NY 199 heads eastward for 1.5 miles (2.4 km) through forested areas to an intersection with NY 9G near the Rhinebeck–Red Hook town line. NY 199 turns northward, overlapping NY 9G through southern Red Hook. The two routes separate east of the hamlet of Barrytown. While NY 9G continues northward, NY 199 heads east through the village of Red Hook and across the hills and fields of northern Dutchess County. Along the way, NY 199 intersects US 9 in Red Hook and the Taconic State Parkway in Milan. Past the latter, it enters the hamlet of Pine Plains, where it is joined by NY 82 from the south. Together, the two highways form the main street of Pine Plains before separating in a more wooded area just east of the community.
East of Pine Plains, the route passes through mostly wooded areas until it reaches the upper Harlem Creek valley. Here, NY 199 turns to the southeast and descends into the valley as it enters the town of North East. The route ends 2.5 miles (4.0 km) to the southeast at an obliquely-angled junction with US 44 and NY 22 southwest of the village of Millerton.
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