 North of the Thruway, NY 65 intersects the eastern terminus of NY 253 and Calkins Road (unsigned NY 943C and a former extension of NY 253) at junctions roughly 1 mile (1.6 km) apart. From this point northward, the route heads through much more developed areas, beginning with a series of housing tracts situated in the 1.5 miles (2.4 km) between Calkins and Jefferson Roads, the latter carrying NY 252. It continues on past NY 252, taking on a more northerly routing as it crosses over the CSX Transportation-owned West Shore Subdivision railroad line and the Erie Canal and passes through densely populated portions of Pittsford and Brighton.
