NY 244 begins at an intersection with NY 19 in the village of Belmont, located southeast of the Southern Tier Expressway in the town of Amity. The route heads northeast on the two-lane Genesee Street, serving several blocks of homes as it crosses the Western New York and Pennsylvania Railroad at-grade and passes over the Genesee River. On the opposite bank, NY 244 changes names to Milton Street at an intersection with the south end of County Route 48. From here, the route continues northeastward out of the village and into less developed areas of Amity. Outside the village limits, the route becomes Mainville Road and runs mostly parallel to Phillips Creek, following it northeast and eastward through a lightly populated valley. The highway meets the southern terminus of CR 2B on its way into the town of Ward, where NY 244 loses the Mainville Road name and the creek ends in the hamlet of Phillips Creek. East of Phillips Creek, NY 244 proceeds across hilly, rural terrain to the town of Alfred, where the highway crosses CR 10 and CR 11 at a junction just east of the town line. Another rugged and undeveloped stretch brings the route into the village of Alfred, a college town home to Alfred University and Alfred State College. NY 244 bypasses most of the village; instead, it connects to downtown by way of North Main Street, here designated but not signed as NY 960B. Outside of the village, NY 244 continues through the town of Alfred and heads along the base of a narrow, lightly populated valley surrounding Canacadea Creek to Alfred Station, where it ends at a junction with NY 21. The intersection is just over south of the village of Almond, where NY 21 connects to the Southern Tier Expressway.
History
The Belmont–Alfred Station road was acquired by the state of New York in stages over the course of the early 20th century. In the town of Amity, the highway was improved under a contract awarded by the state on March 22, 1921. The ensuing project cost $161,802 to complete, and the rebuilt road was added to the state highway system on January 14, 1922, as unsignedState Highway 1559. The part east of Alfred was reconstructed in the mid-1920s as part of a project to connect the Alfred village center and Alfred Station by way of a state road. It was inventoried by the state as SH 1654. In the 1930 renumbering of state highways in New York, SH 1559 and SH 1654 became part of NY 244, a new route extending from Belmont to Alfred Station. In between the two state-owned segments, NY 244 followed an unimproved road through the towns of Ward and Alfred. This segment was rebuilt by the state in the early 1930s. This section became officially part of NY 242 in September 1932. 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 244, NY 248 and its spur, NY 248A in their entirety, NY 275 and sections of NY 408, NY 70 and NY 19. In August 1964, the county declined to sign the offer.
