Located within the Catskill Forest Preserve, NY 296 passes the small Hunter Airport, where views of Rusk Mountain are visible.

Near the junction with Beaches Corners Road, the route turns northwest, paralleling the East Kill, before crossing the waterway a short distance later.

The route proceeds due north after Peck Road, quickly entering a junction with CR 14 (Goshen Street), which merges into the state highway.

After winding down the side of the mountain, NY 296 enters the hamlet of Hensonville, located adjacent to Batavia Kill, a tributary of Schoharie Creek.

The remainder of modern NY 296 was improved under a contract let on April 25, 1912, and accepted into the state highway system on December 19, 1913, as SH 998.