The origins of NY 248 date back to 1912, when most of the route was designated as an unsigned legislative route by the New York State Legislature. The first posted numbers along the route were assigned as part of the 1930 renumbering of state highways in New York. At this time, NY 248 was assigned to the portion of its modern routing north of Greenwood while the section between NY 19 and NY 417 (then NY 17) was designated as New York State Route 17G. NY 248 was extended southwestward over NY 17G in the early 1940s.