NY 392 begins at an intersection with NY 13 and NY 38 in the village of Dryden. The road quickly leaves Dryden, heading eastward through Tompkins County. NY 392, known as Virgil Road, turns to the southeast quickly before turning to the northeast. The area NY 392 passes through is mostly rural, consisting largely of cultivated farmlands. After, NY 392 passes into Cortland County. Now in the town of Virgil, NY 392 intersects with County Route 127A, a spur route of NY 392's predecessor, CR 127. It continues northeast, intersecting CR 128 before entering the hamlet of Virgil. Here, it turns eastward at an intersection with NY 215 and CR 125. Past Virgil, it continues on an easterly routing for before curving to the southeast. After another, the route turns to the north as it enters the community of Messengerville. Once in Messengerville, NY 392 ends at a junction with US 11 just west of Interstate 81.
History
The east–west highway connecting the hamlets of Virgil to Messengerville in the town of Virgil was originally designated as part of NY 90 in the 1930 renumbering of state highways in New York. At the time, NY 90 began in Messengerville and headed northwest to Cortland via Virgil. This section of NY 90 remained unchanged for the next half-century, save for an April 1, 1981, highway maintenance swap that transferred ownership and maintenance of the Virgil–Messengerville segment's easternmost mile from Cortland County to the state of New York. On April 1, 1980, ownership and maintenance of East Main Street and Virgil Road from NY 13 and NY 38 in the village of Dryden to the Tompkins–Cortland county line was transferred from Tompkins County to the state of New York as part of a highway maintenance swap between the two levels of government. One year later, on April 1, 1981, ownership and maintenance of CR 127 and the portion of CR 128 north of CR 127—collectively a single highway linking Virgil Road at the county line to NY 90 in Virgil—was given to the state as part of the aforementioned maintenance swap with Cortland County. Following the second swap, NY 90 was truncated northward to Homer. Its former routing between Virgil and Cortland was redesignated as NY 215 while its old alignment from Virgil to Messengerville became part of NY 392, which also extended westward to Dryden over the newly acquired state highways. Reference markers along the Virgil–Messengerville stretch of NY 392 originally read "90" for the highway's former designation; however, they have since been replaced with markers reading "392".
