 From south to north, the trail summits many small mountains under in elevation, its highest point in New York being Prospect Rock at , and less than half a mile (800 m) from the border with New Jersey.The trail continues north, climbing near Fitzgerald Falls, passing through Sterling Forest State Park, and then entering Harriman State Park and Bear Mountain State Park.In Harriman State Park, the trail passes through the famous Lemon Squeezer, a narrow crack between huge boulders.