Near the bottom of the ramp, at the entrance to the parking area, you'll see a brown post with a yellow arrow, a blue blaze, and 1777W and 1779 blazes. This marks the start of three co-aligned trails: the 1777W and 1779 Trails (which commemorate Revolutionary War events) and the blue-blazed Timp-Torne Trail. Follow these trails up stone steps and under the US 9W viaduct.
Soon, the trails turn left on a paved road. They follow the road for only a short distance and reenter the woods. In another 0.2 mile, the trails turn left onto the paved Mine Road, but in 125 feet, they turn right, leaving the road, and descend on a grassy woods road. In a short distance, the three trails turn left on a footpath, briefly joining the red-on-white-blazed Brooks Lake Trail. The trails cross a wet area on puncheons, then bear left, climb the hillside, and come out once again on the paved Mine Road.
Turn right onto the paved road and follow it for about 500 feet. Just past the intersection with Wildwood Ridge (another road), follow the three trails as they turn left, leave the paved road, and descend into the woods. The trails soon cross a stream on rocks and join a wide woods road - the route of the West Point Aqueduct, built in 1906. At first, the route climbs steeply, but it soon descends and then levels off, with a stone-and-concrete retaining wall to the left. The trails begin to parallel Popolopen Gorge, with the rushing waters of Popolopen Creek visible in places through the trees on the left.
After about two-thirds of a mile along the West Point Aqueduct, you'll reach a trail junction. The 1777W and 1779 Trails continue ahead, following the aqueduct, but you should turn sharply right, following the blue blazes of the Timp-Torne Trail, which climbs gradually on a woods road, soon reaching paved Mine Road. The trail turns left, follows Mine Road for 100 feet, then turns right and begins to climb the Popolopen Torne on stone steps and switchbacks. After a relatively level stretch, the trail turns left and climbs more steeply. Soon, it comes out on a east-facing viewpoint over the Hudson River, the Bear Mountain Bridge and the East Hudson Highlands from a rock ledge.
You'll want to stop here for a short break, but - despite what you might think - this is not the summit of the mountain. Continue ahead on the trail, which makes a sharp bend to the south and continues to climb over rock ledges. In another five minutes or so, you will reach the true summit of the Popolopen Torne, where open rock ledges afford a 360° view. From here, you can see not only the Hudson River and the Bear Mountain Bridge to the east, but also Bear Mountain to the south, and the hills of the West Point Military Reservation to the west.
After spending some time at this beautiful spot, continue ahead as the trail steeply descends the mountain on rock ledges. The descent is much steeper than the climb, and you will have to use both your hands and your feet in places. About halfway down, the trail reenters the woods and continues to descend more moderately on stone steps and switchbacks. You'll cross paved Mine Road and unpaved Fort Montgomery Road and descend to rejoin the 1777W and 1779 Trails at the West Point Aqueduct.
Turn right and follow the three trails (Timp-Torne, 1777W and 1779) along the aqueduct route for 250 feet, then turn left, descend stone steps, and cross Popolopen Creek on a 62-foot footbridge. This prefabricated bridge was installed in 2012 by a volunteer trail crew from the New York-New Jersey Trail Conference, replacing a similar bridge that was severely damaged in 2011 by Hurricane Irene.