The southern terminus of the route was at an intersection with NY 256 south of the community of Scottsburg in Sparta.

While NY 256 headed northwest into a valley surrounding the Conesus Inlet, NY 255 headed northward as Stagecoach Road, running across mostly undeveloped areas along the top of the valley.

East of Scottsburg, NY 255 intersected CR 1A (Springwater Road) and CR 38 (Liberty Pole Road), the former connecting to Scottsburg, before crossing into Conesus.

[1][4] The north–south highway connecting Dansville to Conesus was taken over by the state of New York by 1926.

[6][7] On April 1, 1983, ownership and maintenance of NY 255 was transferred from the state of New York to Livingston County as part of a highway maintenance swap between the two levels of government.