NY 295, meanwhile, was assigned to an alignment extending from Austerlitz to East Chatham. At the time, the route began at an intersection with NY 203 southeast of Chatham and headed to the northeast, bypassing Chatham to the east on Bushnell and Birge Hill Roads. It joined its modern alignment southwest of East Chatham and followed it into the hamlet, where the route ended at a junction with NY 204. The portion of NY 295 south of East Chatham was realigned to follow its current alignment . Around the same time, NY 295 was extended eastward to the state line, replacing part of NY 204. Massachusetts subsequently renumbered Route 204 to Route 295 in order to preserve the number continuity. MA 204 was replaced by MA 295 in 1939.