Stillman/Highlands/Bluebird Trails Loop from Mountain Road

From the parking area, proceed uphill on a wide gravel road, following the yellow blazes of the Stillman Trail. In about half a mile, after crossing a stone-arch bridge, the trail turns left, leaving the gravel road. Just before reaching a north-facing viewpoint over the Hudson River, the teal-diamond-blazed Highlands Trail joins from the left.

The joint Stillman/Highlands Trail now begins to climb on a footpath. With the gravel road just to the right, the trail turns sharply left. At the next sharp left turn, two cairns to the right and a red/blue arrow on a tree to the left mark the start of the red/blue-blazed Bluebird Trail. Turn right onto the Bluebird Trail, which follows around the side of a hill, then climbs gently. After turning left on a woods road, the trail climbs rather steeply on switchbacks. It passes a limited west-facing viewpoint and ends at a junction with the Stillman/Highlands Trail.

Turn left, uphill, and continue on the Stillman/Highlands Trail. A short distance ahead, you'll reach the northern end of the blue-blazed Howell Trail, which leaves to the right. Bear left here, continuing along the yellow/teal diamond-blazed trail, which follows a relatively level route. After a short, steep climb, you'll reach a limited view to the northwest. A few minutes ahead, though, you'll come to a much better viewpoint looking north over the Hudson River. Pollepel Island is directly below, with North and South Beacon Mountain to the right, and the Newburgh-Beacon Bridge in the distance.

Continue ahead, past the summit of Storm King Mountain, with some more views from rock ledges to the left. After a short descent, you'll reach a panoramic north-facing viewpoint, with superb views. Pollepel Island, with the ruins of Bannerman's Castle, is directly below. To the east, Breakneck Ridge (marked by the rail tunnel) is visible across the river. The stone building at the foot of Breakneck Ridge (partially obscured by vegetation) caps a shaft of the Catskill Aqueduct, which tunnels over 1,100 feet below the river. North Beacon Mountain (with communications towers) and South Beacon Mountain (with a fire tower) are to the northeast, and the Newburgh-Beacon Bridge crosses the river in the distance. Beyond, the Shawangunks and Catskills can be seen on a clear day. To the left, the village of Cornwall is below, along the west bank of the river. The rail line running along the east shore of the Hudson is Metro-North's Hudson Line (also the route of Amtrak trains to Albany).

The Stillman/Highlands Trail now continues to descend, soon reaching a junction with the white-blazed By-Pass Trail. Continue along the yellow/teal diamond-blazed Stillman/Highlands Trail, which turns sharply left, immediately reaching another outstanding viewpoint from rock ledges to the right. This viewpoint faces south, with the village of Cold Spring visible across the river to the southeast, and Constitution Island jutting into the river just beyond.

The trail passes more views over the river, then bears left and descends along a beautiful stretch of sidehill trail, through hemlocks and laurel. After passing another panoramic viewpoint to the north, the trail makes a switchback turn. About a third of a mile further on, it descends on another switchback and crosses a wooden bridge over a steep drop at the edge of a cliff.

Shortly thereafter, you'll reach the junction with the Bluebird Trail that you encountered earlier in the hike. Turn right and continue to follow the yellow-blazed Stillman Trail, retracing your steps back to your car.