On July 2, 1935, the Rip Van Winkle Bridge over the Hudson River between Catskill and Greenport was opened to traffic. It became part of a realigned NY 23 after the Athens–Hudson ferry shut down in the late 1940s. NY 23 utilized modern NY 23B between the bridge and Hudson. Plans were made in the early 1950s to construct a southern bypass of the city of Hudson between the Rip Van Winkle Bridge and NY 23 midway between Claverack and Hollowville. Construction on the portion of the highway between the bridge and US 9 south of Hudson began in the mid-1950s and was completed in the late 1950s as a realignment of NY 23. Ultimately, this was the only section that was built; as a result, NY 23 overlapped with US 9 and NY 9H to reach its former alignment in Claverack.