The route continues on, crossing over Owego Creek and passing the Newark Valley Country Club about north of Newark Valley village before entering the town of Berkshire. In Berkshire, NY 38 serves the hamlet of Berkshire, a small community situated directly on the highway. The route continues on through the narrowing creek valley into the town of Richford and the hamlet of the same name, where it meets NY 79 in the community's center. After Richford, the valley continues to narrow for just under before reversing course as the route heads into Cortland County and the town of Harford.