Passing the station, NY 66 also has a junction with the terminus of NY 295 (Railroad Street). Now known as Main Street, the route remains commercial through the northern reaches of the village, turning northwest at a roundabout with Austerlitz Street, River Street and Kinderhook Street. Continuing onto Center Street, NY 66 winds across the northern reaches of the village before crossing into the town of Chatham, where it drops the Center Street moniker. Through the town of Chatham, the route returns to its rural nature, passing a junction with a former alignment of NY 66 that dead-ends in the nearby woods. Turning northwest again, NY 66 enters the hamlet of Old Chatham, where it reaches a junction with CR 13 before crossing Kinderhook Creek.