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Sugarloaf Hill and Osborn Loop Trail
This loop hike follows carriage roads of a former estate and climbs to an outstanding viewpoint over the Hudson River and the Bear Mountain Bridge.
Allowed on leash
Views, Public Transportation
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Trail Conference volunteers maintain trails in this park.
Take the Palisades Interstate Parkway to its northern terminus at the Bear Mountain Bridge. Cross the bridge and proceed north on N.Y. Route 9D for about 4 miles. Look carefully on the right side of the road for a wooden sign "Castle Rock Unique Area." The intersection is also marked by a street sign "Wing and Wing Road." (If you reach the junction of N.Y. Route 403, you've gone too far.) Turn right at the Castle Rock Unique Area sign, passing through a gate with two stone pillars, and bear left at the fork in the road. Continue past a red barn on the right to a gravel parking area.
Take the Metro-North Hudson Line to the Garrison station. A trail leads from the southern end of the parking lot to the trailhead of the hike (see Map 101).
From the parking area, head north into a field. You will notice a blue-blazed trail, which curves to the right. Follow the blue-blazed trail east across the field, with blazed posts marking the route. At the eastern edge of the field, the trail climbs into the woods, soon reaching a woods road. Follow the blue-blazed trail as it turns right onto the woods road and descends slightly. Soon, you’ll reach a panoramic viewpoint to the northwest over Storm King Mountain, the West Point Military Academy and the East Hudson Highlands.
Just beyond, the blue-blazed trail ends at a junction with the red-blazed Sugarloaf Trail, which comes in from the right. A rustic gazebo is on the left. Continue ahead 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 turns and 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. After crossing the summit ridge, the trail descends a little and 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 on the right and a gazebo on 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 (A.T.).
Proceed straight ahead on the carriage road, now following the white blazes of the A.T. on a relatively level route. In about a mile, the yellow-blazed Curry Pond Trail leaves to the right. Continue ahead on the white-blazed A.T., which soon begins to descend. After bearing sharply right at a junction with another woods road, the A.T. reaches the southern end of the Osborn Loop Trail. The A.T. 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 large cairn on the left which marks a yellow-blazed trail that leads to Manitoga. Continue ahead on the blue-blazed trail, which soon crosses a stream and reaches (on the right) the western end of the yellow-blazed Curry Pond Trail. Just beyond, on the left, an unmarked woods road heads downhill to Manitoga, but you should continue ahead on the Osborn Loop Trail. A short distance ahead, follow the trail as it turns right, leaving the carriage road, and descends to cross a stream. After climbing to a limited 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. You’re now retracing the route you followed at the start of the hike. When you reach the gazebo at the edge of the field, turn left, descend across the field on the red-blazed trail, and follow woods roads back to the parking area where the hike began.