Take I-287 to Exit 57 and continue on Skyline Drive to its western end at Greenwood Lake Turnpike (County Route 511) in Ringwood. Turn right and proceed for 8.2 miles to an intersection with Lakeside Road. Turn right and follow Lakeside Road (still designated County Route 511) for 2.4 miles to the Greenwood Lake Marina, just south of the New Jersey-New York boundary. Turn left and park on the left side of the dirt access road, west of Lakeside Road. Do not, under any circumstances, park on the private property of the Greenwood Lake Marina, on the east side of Lakeside Road.
This is one of the most spectacular hikes in the New Jersey-New York metropolitan area. Although it begins with a fairly strenuous 600-foot climb, the rest of the hike does not involve any major elevation changes. There are, however, many short, steep ups and downs, some of which require you to use your hands as well as your feet. The estimated time of four hours will allow you plenty of time to pause and enjoy the wonderful scenery that you'll encounter along the route.
From the kiosk at the end of the parking area, bear left onto the blue-on-white-blazed State Line Trail, which follows a wide, rocky path up Bearfort Mountain. The ascent is moderate at first, and the trail soon levels off. With a private home visible directly ahead, the trail turns right and begins to climb more steeply. Take care to follow the blue-and-white blazes, as there are many side trails that branch from the main route.
In about three-quarters of a mile, you’ll reach an intersection with the yellow-blazed Ernest Walter Trail (marked by a cairn). Bear left and follow the yellow-blazed trail uphill. Soon, you begin to traverse a long, glacially-smoothed outcrop of Schunemunk Conglomerate “puddingstone” rock. This unusual reddish-matrix conglomerate rock – studded with pebbles of pink sandstone and white quartz – is characteristic of the Bearfort Ridge. As you climb along the rock outcrop, views open up over Greenwood Lake to the east.
Continue to the top of the outcrop, which offers a panoramic view over the six-mile-long lake, 600 vertical feet below. The hills of Sterling Forest are in the background and, on a clear day, you can see the Sterling Forest Fire Tower in the distance. You’ll want to spend some time here, taking in the magnificent view and resting from the steep climb.
When you’re ready to resume the hike, continue along the Ernest Walter Trail, which briefly dips into the woods, but soon comes out again on another long conglomerate outcrop. After passing through an area studded with pitch pines, with more views over Greenwood Lake, the trail bears right and descends to cross the outlet of a wetland to the right of the trail. A short distance beyond, it reaches the eastern shore of pristine, spring-fed Surprise Lake. Again, you’ll want to stop here to experience the beauty of this wilderness lake. Swimming is not permitted, however.
The yellow trail heads south from the lake, immediately reaching the start of the orange-blazed Quail Trail, which continues ahead. You should bear right to continue along the Ernest Walter Trail. In a short distance, you’ll begin to pass through a dense rhododendron grove. In several places, the thick rhododendrons actually form a canopy over the trail!
After descending a little, the trail crosses Cooley Brook, the outlet of Surprise Lake, on rocks and logs. This crossing may be difficult if the water is high. The trail now climbs to reach an east-facing viewpoint from a rock outcrop studded with pitch pines at the northern terminus of the white-blazed Bearfort Ridge Trail. The hills of Sterling Forest and the Wyanokie Plateau are directly ahead, with an arm of the Monksville Reservoir beyond. On a clear day, you can see the skyscrapers of Manhattan in the distance. If there are no leaves on the trees, you might be able to see Surprise Lake through the trees to the left.
Continue along the yellow-blazed Ernest Walter Trail, which heads west, crossing many sharp ridges of the mountain. This section of trail is particularly rugged, with many short but steep ups and downs. At the bottom of the second steep descent, you’ll come to a T-intersection. Turn right, following a yellow arrow on a tree, and continue for about 150 feet to a rock outcrop overlooking pristine West Pond. You’ll want to spend a little time at this special spot, enjoying the view!
When you’re ready to continue, retrace your steps to the trail junction and continue ahead, heading west along the Ernest Walter Trail. You’ll soon come to a third, very steep descent, at the base of which the trail crosses Green Brook, the outlet stream of West Pond. The trail now proceeds through an attractive forest of hemlocks, pines and deciduous trees. After a while, there are seasonal views of West Pond through the trees to the right.
About half a mile from Green Brook, the trail crosses a small stream, the outlet of a wetland to the left. Just beyond, a rock outcrop to the left of the trail affords a view over the wetland. An unusual huge split boulder adds interest to this spot, which is another good place to take a break.
Soon, the trail traverses a long, narrow, smooth rock. A short distance beyond, it turns right and descends to end at a junction with the white-blazed Appalachian Trail (A.T.). Turn right onto the Appalachian Trail, which almost immediately climbs a steep ledge. You’re now heading east, again crossing several sharp ridges. At a limited viewpoint to the east, the trail turns left and heads north (when there are no leaves on the trees, Surprise Lake is visible below).
After about a third of a mile on the A.T., you’ll reach another limited viewpoint, with both east- and west-facing views from an open rock ledge. The A.T. now descends a long, sloped rock and reaches a junction with the blue-and-white-blazed State Line Trail (the junction is marked by paint blazes on a rock). Turn right and follow the State Line Trail, which crosses several ridges and then begins a steady descent. In about half a mile, you’ll reach the junction with the yellow-blazed Ernest Walter Trail that you encountered earlier in the hike. Continue along the State Line Trail, which descends steadily to the parking area on Lakeside Road where the hike began.