The origins of NY 296 date back to the early 1910s when the highway was improved by the state of New York over the course of two separate projects. On February 19, 1910, the state awarded a contract to rebuild  of roads in Windham, including the northernmost  of what is now NY 296.
The origins of NY 296 can be traced back to the early 1910s when New York State undertook two separate projects to improve the highway. On February 19, 1910, a contract was awarded for road reconstruction in Windham, which included the northernmost section that is now NY 296.