New York State Route199 (NY199) is a 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 expressway 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 Route41, a new route connecting Barrytown to Millerton, in the mid-1920s. NY41 was renumbered to 199 as part of the 1930 renumbering of state highways in New York. When the Kingston–Rhinecliff Bridge opened in 1957, NY199 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 Route82 (CR82). Route description Route 9W to Red Hook The western terminus of Route 199 is the northern terminus of U.S. Route 209 in Ulster County. When the expressway 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 (1.6km), with the eastbound lanes reaching the toll gantry for the Kingston–Rhinecliff Bridge further on. West of the toll gantry, the expressway ends as the road narrows to two lanes to cross the 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 has its first traffic light at the intersection with River Road (also County Route 103). At