it has reached. After some tight curves and bends, SUNY's athletic fields to the east herald entry into the village of New Paltz, where NY 208 becomes South Chestnut Street. A mile into the village, it reaches its northern terminus at a busy intersection at the edge of downtown with NY 299 and NY 32. Continuing north from here puts a driver on the latter. History The earliest of the road segments that make up NY 208 dates to 1735, when a "Highway Deed" was drawn up for a segment in the Town of Montgomery, then in Ulster County, from the Shawangunk town line to what was then the Goshen town line (today Hamptonburgh). When it came to acquire a name, it was first Walden Road. In 1950, Maybrook renamed its portion Homestead Avenue in honor of early settlers whose houses stood or had stood along the road. Designation NY 208 was assigned to its current routing between Monroe and Gardiner in the 1930 renumbering of state highways in New York. The route was extended north to its current terminus in New Paltz . Prior to 1930, the entirety of NY 208 was unnumbered. When US 6 was rerouted to follow the new Quickway and NY 32 between Monroe and Central Valley in the mid-1950s, NY 208 was extended northeast from Monroe along the former routing of US 6 to Highland Mills, where it terminated at NY 32. This extension of NY 208 remained in place until April 1, 1980, when ownership and maintenance of NY 208 from Schunnemunk Street in Monroe to Highland Mills was transferred to Orange County as part of a large highway maintenance swap between the county and the state of New York. Following the swap, NY 208 was rerouted within Monroe to follow its current alignment between NY 17M and Schunnemunk Street while the former routing of NY 208 between Monroe and Highland Mills was redesignated as County Route 105. In 2006, the portion of the route between Washingtonville and New Paltz was also designated as State Bicycle Route 208. New Jersey connection In the 1940s, the New Jersey Department of Transportation planned to link a spur route then called Route S4B from Paramus up though Bergen County to connect with NY 208 at Monroe. The road never got any further than Oakland, but it was renumbered to Route 208 in 1953. Traffic congestion The