New York State Route 199

New York State Route 199
Map of the Mid-Hudson Valley with NY 199 highlighted in red
Route information
Maintained by NYSDOT and NYSBA
Length	30.91 mi[1] (49.74 km)
Existed	1930[2]–present
Major junctions
West end	US 9W / US 209 in Ulster
Major intersections	NY 32 in Ulster NY 9G in Rhinebeck US 9 in Red Hook NY 308 in Red Hook Taconic State Parkway in Milan NY 82 in Pine Plains
East end	US 44 / NY 22 in Millerton
Location
Country	United States
State	New York
Counties	Ulster, Dutchess
Highway system
New York Highways Interstate US State Reference Parkways
← NY 198 → NY 200

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).