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 the highway was upgraded by the state of New York in two separate projects. On February 19, 1910, the state awarded a contract for road reconstruction in Windham, including the northernmost section that is now NY 296.