NY 308 begins from its western terminus at an intersection with US 9 in the Dutchess County village of Rhinebeck, at about in elevation. It is within the Rhinebeck Village Historic District, a historic district that contains 272 buildings in a variety of architectural styles dating from over 200 years of the settlement's history. One of those buildings, the Beekman Arms Inn, at the corner of routes 9 and 308, claims to be the oldest continuously-operated inn in the United States. founded in 1766.