NY 256 begins at an intersection with NY 63 in the village of Dansville. It initially heads northeastward on Perine Street, following it past five residential blocks to a junction with Health Street on the northeastern edge of the village. Perine Street ends here; however, NY 256 continues to the north on Health Street, following the street out of both Dansville and the Canaseraga Creek valley that contains the village. Outside of the valley, the route travels north through the rural towns of North Dansville and Sparta, passing by farmland on its way to a junction with County Route 71, once designated as NY 255. While CR 71 heads northeast toward the hamlet of Conesus, NY 256 continues northwest to serve Scottsburg, a small community in the far northwestern corner of the town of Sparta. North of Scottsburg, NY 256 heads into the town of Conesus and enters the south end of the Conesus Lake valley. Here, it follows the west bank of Conesus Inlet past a marshy area that eventually leads to the southern end of Conesus Lake. The route continues on, following the western lakeshore through the towns of Groveland and Geneseo as West Lake Road. Along this stretch, NY 256 serves many lakeside homes and communities. At Graywood, a community south of the lake's north end, NY 256 joins the Geneseo–Livonia town line and follows it for the remainder of its routing. From this point north, the route traverses lightly populated areas dominated by farmland. NY 256 crosses US 20A west of Lakeville—a hamlet situated at the northern tip of Conesus Lake—before ending about later at a junction with NY 15.
History
NY 256 was assigned as part of the 1930 renumbering of state highways in New York. It initially began at NY 36A in the hamlet of Groveland and followed Scottsburg Road east to Scottsburg, where it turned north to follow West Lake Road to a terminus at NY 254 west of Lakeville. NY 256 was rerouted to follow a new highway connecting Scottsburg to NY 255 southeast of the hamlet. The route was extended north to US 15 and south to Dansville by way of NY 255 in the early 1940s. NY 255 was then truncated to its junction with NY 256. On April 1, 1983, ownership and maintenance of NY 256 between NY 63 and Depot Road in Dansville was transferred from Livingston County to the state of New York as part of a highway maintenance swap between the two levels of government.
