of the Manchester village center. Past the Thruway, NY 21 becomes rural in nature once more as it runs across rolling terrain to the Wayne County line. Within Wayne County, the area around NY 21 becomes more developed as it enters the village of Palmyra, where the road is village-maintained from the southern village line to its junction with NY 31 in the village's historic center. The route briefly overlaps NY 31 along East Main Street before crossing both the Erie Canal and the CSX Transportation-owned Rochester Subdivision on its way out of the village. From Palmyra to Williamson, the land surrounding NY 21 is predominantly rural in nature. However, midway between the two locations, NY 21 comes close to the hamlet of Marion, which it bypasses to the west. In Williamson, NY 21 passes through the town center at a junction with Ridge Road before ending at an intersection with NY 104 in a more commercial section of the town. History Origins Prior to the American Revolution, the path of modern NY 21 north of Canandaigua was part of an old Native American trail connecting Seneca Lake to Lake Ontario by way of Canandaigua Lake. The trail began in the vicinity of Geneva and went west to Canandaigua on a path now occupied by US 20 and NY 5. It continued north from Canandaigua, passing through the village of Palmyra and the hamlet of Marion before reaching the Lake Ontario shoreline at Pultneyville. Construction to convert the Canandaigua–Marion section of the trail into a road was completed in 1794. The remainder of the trail north to Pultneyville was converted into a road approximately three years later. The Canandaigua–Pultneyville highway served as a post road in the years that followed. At some point, the section of the highway between Palmyra and Marion, initially a corduroy road, was rebuilt as a plank road and tolled. The highway fell into disrepair over the years, leading travelers to conceive ways to avoid paying toll. The toll booths were eventually removed, and the road was later covered with dirt and converted into a stage road. By the 1920s, the state of New York had assumed ownership of the Canandaigua–Pultneyville highway. In the mid-1920s, it became part of NY 72, a north–south highway extending from NY 52 in Naples to the Lake Ontario shoreline in Pultneyville by way of the western side of Canandaigua Lake.