Description:

From the parking area, retrace your steps along the road. When you reach the fork, turn left (east), then turn right at the next intersection. In a few hundred feet, you will see a sign to the left marking the start of the trail. Turn left and follow a footpath which climbs across a field to reach a woods road at the edge of the forest. A wooden gazebo located here invites one to pause and enjoy the pastoral setting, with West Point and the Highlands in the background.

From the gazebo, proceed south on the woods road, now following the red blazes of the Sugarloaf Trail. The trail soon turns sharply left and ascends on another woods road. After several switchbacks, you'll pass a pond on the left and then reach a trail junction in the broad saddle between Castle Rock and Sugarloaf Hill. Turn right here, and continue to follow the red blazes, which now mark a footpath that steeply climbs to the summit of Sugarloaf Hill. Just beyond the summit, the trail ends at a rock outcrop, with a magnificent view to the south over the Hudson River and the Bear Mountain Bridge.

After enjoying the view, retrace your steps and return to the trail junction in the saddle. Now proceed straight ahead on the blue-blazed Osborn Loop Trail. Named after a prominent family in the area who donated the land traversed by the trail, the Osborn Loop Trail follows carriage roads of the former estate. The trail climbs gently and, after passing a small pond to the right and a gazebo to the left, reaches a junction with the yellow-blazed Carriage Connector Trail. Continue ahead on the blue-blazed trail, which soon resumes its climb, passing through thick stands of mountain laurel. After leveling off, the Osborn Loop Trail ends a junction with the white-blazed Appalachian Trail. You're now about halfway through the hike (including the side trip to Sugarloaf Hill).

Proceed straight ahead on the carriage road, now following the white blazes of the Appalachian Trail on a relatively level route. In about 500 feet, you'll notice a blue-blazed side trail on the right, which leads a short distance to a rock outcrop with a limited view over the Hudson River. About a mile beyond, the yellow-blazed Curry Pond Trail leaves to the right. Continue ahead on the Appalachian Trail, which soon begins to descend. After bearing sharply right at a junction with another woods road, it reaches the southern end of the Osborn Loop Trail. The Appalachian Trail turns left here, but you should continue ahead, now once again following the blue blazes of the Osborn Loop Trail.

In about half a mile, you'll notice a trail leaving to the left, blazed with both branded wooden markers and white discs. This trail leads to the Manitoga Nature Preserve. Then, a short distance ahead on the blue-blazed trail, you'll pass the western end of the yellow-blazed Curry Pond Trail. Continue ahead on the Osborn Loop Trail, which soon turns right, leaving the carriage road, and descends to cross a stream. After climbing to a viewpoint over the Hudson River, the trail again descends. It crosses another stream and climbs to the trail junction in the saddle between Sugarloaf Hill and Castle Rock.

Continue straight ahead at the junction, and descend on the red-blazed Sugarloaf Trail. When you reach the gazebo at the edge of the field, turn left, descend across the field, and follow the woods roads back to the parking area.