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 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.