Kent: Hillside Roads & Housatonic River

These pristine roads in the Kent hillside are about as scenic as the New England countryside gets. We’ve mapped a lovely 8-mile loop, skirting Pond Mountain and featuring a tough hill climb. Starting at the Kent School, climb Macedonia Road until the intersection with Macedonia Brook Road and turn RIGHT. At the fork, bear right on Fuller Mountain Road and wrap around Fuller Pond — this is the hilliest section of the route. This stretch is marked by long winding stone walls, saltbox homes, and rolling farmland views. At the next fork, bear RIGHT again on Skiff Mountain Road which winds around Pond Mountain Natural Area to the Housatonic River. Keep west along the river for a flat amble back to the start.