From the kiosk, follow the aqua-blazed Long Path, which heads north into the woods. In 0.3 mile, after a short descent, you'll reach a junction. Here, the red-square-on-white Popolopen Gorge Trail begins to the right, but you should bear left to continue on the Long Path, which begins a gradual climb. Soon, the trail bears right and climbs more steeply. As it approaches the 1,155-foot summit, the grade moderates.
Chiseled into the rock on the summit is a memorial to Raymond H. Torrey, who served as President of the New York-New Jersey Trail Conference from 1931 until his death in 1938. It was Torrey who scouted this trail section in 1922. The summit affords a panoramic east-facing view, with Turkey Hill Lake below and Bear Mountain (with the Perkins Memorial Tower on its summit) beyond.
After taking in the magnificent view, continue ahead on the Long Path. From the northern end of the summit ridge, there is a broad view to the north over the hills in the West Point Military Reservation, with the rocky Popolopen Torne visible to the right (north of Bear Mountain). The Long Path now bears left and descends steadily on switchbacks.
At the base of the descent - just before the crossing of Deep Hollow Brook - turn left onto an unmarked woods road. This road, known as the Deep Hollow Road, was constructed by the Civilian Conservation Corps in 1934. The CCC workers laid a base of broken stone, but never completed the road by overlaying it with a layer of gravel. Head south on Deep Hollow Road, which briefly parallels the brook, then begins a gradual climb.
In half a mile, you'll reach the junction of the Long Path with the Popolopen Gorge Trail at the base of Long Mountain. Turn right and retrace your steps along the Long Path to the parking area where the hike began.