Once across the bridge and into Columbia County, the highway encounters NY 9G near the Olana State Historic Site in western Greenport. The two highways briefly overlap until NY 9G continues north with NY 23B to follow NY 23's old course into and through the city of Hudson. NY 23 continues to the southeast, bypassing Hudson well to the south and serving Columbia–Greene Community College, located in an otherwise forested area of Greenport. After , the route meets US 9 at an isolated junction due south of Hudson. US 9 and NY 23 overlap for across more open but still largely undeveloped areas to a small, unnamed community on the western edge of Bell Pond, a small waterbody in the northeast corner of the town of Livingston.