In 1908, the New York State Legislature created Route 1, an unsigned legislative route extending from New York City to Rensselaer. Route 1 left modern NY 22 at the hamlet of Amenia and followed what is now U.S. Route 44 west to Smithfield Valley Road. From there, the route headed north through the town of North East and northwest through the town of Pine Plains to the community of Pine Plains by way of Smithfield Valley Road. Route 1 continued northward on Silvernails and Gallatinville Roads and modern CR 7 to the hamlet of Ancram, where it turned northeast to follow today's CR 7 toward Copake. On March 1, 1921, Route 1 was realigned between Amenia and Copake to use modern NY 22 instead.
