As the road changes names to Spring Street, the Stony Kill approaches from the west and roughly parallels NY 295 for much of its duration.

The highway proceeds towards the northwest as it passes to the east of a pond, and subsequently intersects the Taconic State Parkway.

Upon crossing the state parkway, NY 295 takes a more easterly direction; however, it turns towards the northwest when it reaches New Concord Road.

The road intersects the Berkshire Connector of the New York State Thruway, or Interstate 90 (I-90), and enters the hamlet of East Chatham shortly after.

The road bends towards the southeast into Canaan, where the Stony Kill turns sharply towards the north, and NY 295 crosses the Queechy Lake Brook.

Crossing between two mountains, the highway passes to the southwest of Queechy Lake, and intersects with NY 22.

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.