lake itself. Near Woodville, a hamlet north of Naples, the route briefly enters Yates County for just over a half-mile (0.8 km) before reentering Ontario County. It serves lakeside homes and cottages in the town of South Bristol for another , after which the road begins to climb the side of the valley and meander toward the hamlet of Bristol Springs. Here, the road forks, with NY 64 beginning to the left (west) and NY 21 continuing to the right (north). While NY 64 heads northwest to Rochester, NY 21 progresses to the northeast, overlooking Canandaigua Lake on its way through mostly isolated areas of the town of Canandaigua. The route eventually reaches the outskirts of the city of Canandaigua, where it intersects US 20 and NY 5. At this point, NY 21 turns east, joining US 20 and NY 5 as all three routes head around the southwestern portion of the city. The primary portion of the bypass ends about later at an intersection with South Main Street; the junction also marks the east end of the overlap between the three routes and the south end of NY 332. NY 21 turns north onto South Main Street, following NY 332 through the city's historic downtown district. The two routes pass by 426 South Main Street, Benham House, and the city's former United States Post Office, all properties listed on the National Register of Historic Places, before splitting at the junction of Gibson and North Main streets. NY 332 continues north from this point on North Main Street toward Victor while NY 21 follows Gibson Street northeastward through a residential section of the city. It passes Sonnenberg Gardens and Mansion State Historic Park and the city's VA Hospital before leaving the Canandaigua city limits. Outside the Canandaigua city limits, the area surrounding NY 21 becomes rural once again; however, the surrounding terrain is more level than it was south of the city. The route heads northeast through farmland to Chapin, a small hamlet in the town of Hopewell, where it intersects the south end of NY 488 and turns to take on a more northerly course. Not far to the north are the adjacent villages of Shortsville and Manchester, roughly separated by the Ontario Central Railroad. Here, NY 21 passes under the railroad and intersects both NY 96 and the New York State Thruway (I-90) at exit 43 just north