New York State Route 199

New York State Route 199 (NY 199) is a 30.91-mile-long (49.74 km) state highway located in the Hudson Valley of the U.S. state of New York. Its western end is in Ulster County, where it begins as the continuation of the short U.S. Route 209 freeway east of its interchange with U.S. Route 9W; after crossing the Kingston–Rhinecliff Bridge over the Hudson River the rest of the highway crosses northern Dutchess County. As it does it passes through downtown Red Hook and Pine Plains, reaching its eastern end at U.S. Route 44 and State Route 22 southwest of Millerton in the upper Harlem Valley.

The portion of Route 199 east of its junction with the Taconic State Parkway was originally part of the Ulster and Delaware Turnpike, a toll road linking Bainbridge to Salisbury, Connecticut. This segment of the turnpike was incorporated into New York State Route 41, a new route connecting Barrytown to Millerton, in the mid-1920s. NY 41 was renumbered to 199 as part of the 1930 renumbering of state highways in New York.

When the Kingston–Rhinecliff Bridge opened in 1957, NY 199 was realigned to continue across the bridge to the town of Ulster. The former routing of the highway between Barrytown and NY 9G along Barrytown Road remained state maintained until 1980, when ownership and maintenance of the highway was transferred to Dutchess County. It is now designated as County Route 82 (CR 82).

The western terminus of Route 199 is the northern terminus of U.S. Route 209 in Ulster County. When the four-lane freeway section of the latter road reaches the cloverleaf interchange with US 9W, in the town of Ulster, between Kingston and Lake Katrine, it assumes the 199 designation as it continues eastward through woodlands. Veering slightly northward, it has another interchange with State Route 32 after a mile (1.6 km), with the eastbound lanes reaching the toll gantry for the Kingston–Rhinecliff Bridge 0.4 miles (640 m) further on.

West of the toll gantry, the highway becomes a two-lane freeway before crossing the 1.5-mile (2.4 km) bridge, on an east-southeast heading. On the east bank, now in the Dutchess County town of Rhinebeck, it remains two lanes as it traverses wooded areas, part of the Hudson River Historic District, a National Historic Landmark. The road returns to a due-east course shortly after the crossing; it becomes a two-lane expressway and has its first traffic light at the intersection with River Road (also County Route 103).

At 0.6 miles (0.97 km) past that intersection, the highway reaches another traffic light at State Route 9G. It joins that highway northbound, immediately entering the town of Red Hook, for a two-mile (3.2 km) stretch through woodlands, first heading northwest then due north. The two lanes widen to four on either side of the Rokeby Road intersection.

The 9G concurrency ends a mile to the north, where the roadway reaches another traffic light after a bend northeast. Here NY 199 turns east, going over a slight rise and then trending slightly southward towards the village of Red Hook. At the village line, a mile east of NY 9G, it passes Red Hook High School, the historic Maizefield estate, and the middle school, becoming West Market Street. At the center of town, another traffic light marks the intersection with U.S. Route 9.

NY 199 becomes East Market Street and leaves the village approximately a half-mile (800 m) to the east, curving gently through a mix of fields and woodlots in the surrounding landscape. A mile (1.6 km) past the village, the road makes the first of four crossings of the Saw Kill. After crossing the Lakes Kill a thousand feet (300 m) further on, the road starts a long turn southeastward past the former Sky Park Airport and Red Hook Golf Club.