NY 248 begins at an intersection with NY 19 in the hamlet of Stannards, located within the town of Willing. It heads generally eastward from the community as Hallsport Road, following Chenunda Creek into a largely rural portion of the town. Here, the route passes by a series of fields and a handful of isolated homes before leaving the creek and entering Hallsport, a small community near the eastern town line. Past Hallsport, NY 248 follows a more southeasterly routing for just under to the town line, where it turns back to the east as it proceeds into the town of Independence and becomes known only by its route number. About into Independence, the highway makes a sharp curve to the south into a more forested area of Allegany County. At this point, the route begins to descend in elevation as it heads through a small valley surrounding an offshoot of Cryder Creek. Just outside Whitesville, the small, narrow valley gives way to a wider one surrounding Cryder Creek itself, and NY 248 turns eastward into the latter valley to enter Whitesville as Main Street. In the hamlet, NY 248 intersects its lone spur route, NY 248A, and crosses Cryder Creek, which splits into Marsh and Spring Mills Creeks a short distance to the northeast. At the eastern edge of Whitesville, NY 248 turns northward onto Wildman Avenue, crossing over Spring Mills Creek and following Marsh Creek northeastward out of both Whitesville and Allegany County.
Steuben County
Across the county line in Steuben County, NY 248 passes through rural, forested areas as it proceeds northeast along the base of a valley surrounding Marsh Creek. Roughly into the town of West Union, the creek gives way to a large, marshy lake, which NY 248 straddles while proceeding northeastward, and later southeastward through the valley. The valley ends southeast of the hamlet of Barney Falls and from the county line, allowing the route to turn northward and enter Rexville, a small community based around the junction of NY 248 and County Route 117. Here, NY 248 joins Bennetts Creek, which the route follows for the rest of its existence. Outside of Rexville, the route heads north through another forested valley—this time surrounding Bennetts Creek—to the town of Greenwood and the hamlet of the same name, the largest location on the route between Whitesville and the village of Canisteo. NY 248 heads north–south through the community, serving as its main street, before intersecting NY 417 north of the hamlet. The route continues on, passing through sparsely populated areas of the towns of Greenwood and Canisteo as it proceeds along the base of a wider, less pronounced valley around Bennetts Creek. The surroundings change immediately upon crossing over Purdy Creek and into the village of Canisteo, where NY 248 becomes Greenwood Street and passes by the village's schools and several densely populated village blocks. After eight blocks, the street and the route come to an end at Main Street.
History
The portion of modern NY 248 east of Whitesville was originally designated as Route 4-b, an unsigned legislative route, by the New York State Legislature in 1912. On March 1, 1921, Route 4-b was renumbered to Route 46 and extended westward along what is now NY 248 and NY 19 to Wellsville. No part of legislative Route 46 was assigned a posted designation when the first set of posted routes in New York were assigned in 1924; however, the entire route received a number as part of the 1930 renumbering of state highways in New York. From Stannards to Greenwood, legislative Route 46 was designated as NY 17G, a southerly alternate route of NY 17. The section of the route between Stannards and Wellsville became part of NY 19 while the remainder of old Route 46—from Greenwood to Canisteo—became NY 248. NY 17G became part of an extended NY 248 in the early 1940s. In 1964, the New York State Department of Public Works proposed trading over of roads that were not managing 1,000 or more cars daily for the construction of of the Southern Tier Expressway. This list of proposed transfers included NY 248 and its spur, NY 248A in their entirety, along with NY 244, NY 275 and sections of NY 408, NY 70 and NY 19. In August 1964, the county declined to sign the offer.
Major intersections
NY 248A
NY 248A is a spur connecting NY 248 to the Pennsylvania state line in Allegany County. The route originates at the state line in Willing and continues northeast along the northern edge of a valley surrounding Cryder Creek to Whitesville, where it terminates at NY 248. NY 248A becomes Pennsylvania Route 244 upon entering Pennsylvania. The route was assigned in September 1950.
