Rip's Rock Loop

This moderate route begins near the Winter Clove Inn, just south of Round Top, and climbs through the mossy hardwood and hemlock forest of the Windham-Blackhead Range Wilderness. The trail follows a lightly used path that may be faint in places but is generally easy to follow with basic navigation skills. Early on, the route crosses seasonal streams before beginning a steady, occasionally steep climb over rocky terrain. Around halfway in, a short scramble leads to a broad ridge where the forest opens and the grade eases. Continuing along the ridge, stay right at a subtle Y-intersection to remain on the main trail toward Rip’s Rock. The overlook marks the end of the route, offering sweeping views across Kaaterskill Clove and distant peaks of the eastern Catskills. This route sees light foot traffic and provides a good chance for solitude and wildlife sightings. Return the way you came, watching for slick rocks and roots on the descent.