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Appalachian Trail /Osborn Loop Trail from Route 9
This loop hike follows footpaths and carriage roads of a former estate through mountain laurel thickets.
Allowed on leash
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Take the Palisades Interstate Parkway to its northern terminus at the Bear Mountain Bridge. Cross the bridge and bear left onto N.Y. 9D. Proceed north on N.Y. 9D for 4.5 miles, and turn right onto N.Y. 403. Continue on N.Y. 403 for 2.1 miles to Cross Road (just north of the terminus of N.Y. 403 at U.S. 9). Turn left onto Cross Road (a one-block road that leads to U.S. 9) and park along the shoulder of the road.
Follow N.Y. 403 or U.S. 9 south to their intersection. Here, you will see the white blazes of the Appalachian Trail, which crosses the intersection. Turn right and follow the trail across a former pasture on a boardwalk, then continue uphill on a old carriage road. In half a mile, after crossing a stream, follow the white blazes as they turn uphill and begin a steeper climb on a footpath. (Ahead, the carriage road is the route of the yellow-blazed Carriage Connector Trail, which will be your return route.) Near the top of the hill, turn sharply left, as the blue-blazed Osborn Loop Trail leaves to the right. You now join another carriage road - this one being relatively level.
A short distance beyond, another blue-blazed trail leaves to the right. Follow this side trail a short distance to a viewpoint over the Hudson River. Although the view is partially obscured by the trees, you can see the Bear Mountain Bridge to the south and West Point across the river to the north. This is a good place to take a rest from your steep climb.
When you're ready to continue, return to the Appalachian Trail and turn right. Follow the Appalachian Trail for another three-quarters of a mile along a relatively level carriage road, with a few gentle ups and downs. After a short climb, you'll notice a cairn and a triple yellow blaze to the right of the trail, marking the start of the Curry Pond Trail. Turn right, leaving the carriage road, and follow the yellow blazes along a footpath. (You may see a few yellow blazes on trees to the right of the trail about a quarter of a mile from the viewpoint. These yellow blazes mark the Appalachian Trail corridor boundary and should be disregarded.)
Follow the Curry Pond Trail as it descends through dense mountain laurel thickets, steeply in places, and passes interesting rock outcrops. After crossing its inlet stream, the trail loops around Curry Pond, with the pond to the left. It crosses the pond's outlet stream and soon ends at a junction with the blue-blazed Osborn Loop Trail.
Turn right and follow the Osborn Loop Trail north. The trail briefly follows a carriage road, but soon turns right and descends to cross a stream. It continues along the side of Canada Hill and, after crossing a few more small streams, bears left and climbs along an old stone wall. At the top of the climb, it bears right, with views to the left through the trees over the Hudson River.
Follow the blue-blazed trail as it descends from the crest of the ridge, first gently, then more steeply, paralleling a stream. At the base of the steep descent, marked by a cairn, the Osborn Loop Trail turns right onto a woods road and continues to descend more gradually through mountain laurel and hemlocks. The trail crosses a stream at a cascade and climbs gently to reach a junction with the red-blazed Sugarloaf Trail, which is ahead and to the left.
Turn right at this junction, continuing to follow the blue-blazed Osborn Loop Trail. You're now on a wide, well-engineered carriage road, supported by a stone wall on the right side. In a short distance, you'll notice an attractive gazebo to the left of the trail - another good place to take a break.
Continue ahead on the Osborn Loop Trail, which now parallels a stream to the right. After passing a small pond, with a stone dam, to the right, you'll reach a junction. Here, the blue-blazed Osborn Loop Trail turns right, but you should continue ahead on the carriage road, now following the yellow blazes of the Carriage Connector Trail. Bear right at the next junction and continue along the yellow-blazed trail, passing through dense mountain laurel and hemlock. After bearing right at the next two trail junctions, the trail narrows and goes slightly uphill, then passes a wetland to the right.
When the Carriage Connector Trail ends at a junction with the white-blazed Appalachian Trail, continue ahead along the carriage road, now following the white blazes. Retrace your steps along the Appalachian Trail until you reach the intersection of Routes 403 and 9, then turn left and continue to Cross Road, where you parked your car.