Shortly after the NY 9H junction, NY 217 splits off to the northeast toward Philmont. The road continues southeastward from NY 217, crossing over Claverack Creek and leaving the built-up hamlet of Claverack for countryside more open and less rugged than that in the Catskills. It proceeds generally easterly across mostly undeveloped fields to Martindale, a small community at the interchange linking NY 23 to the Taconic State Parkway. From here, NY 23 follows a creek valley southeast and east into Hillsdale, where the route connects to NY 22, a north–south highway that closely parallels New York's eastern state line for most of its length. Almost to the east, NY 23 reaches the state line, where it becomes Massachusetts Route 23 as it serves the bi-state Catamount Ski Area.