Sugarloaf Mountain and Breakneck Ridge Trail
Directions to trailhead
From the east end of the Bear Mountain Bridge, proceed north on Route 9D for about 8.5 miles to the Village of Cold Spring. Continue ahead on Route 9D for another two miles (beyond the intersection with Route 301 in Cold Spring) and pass through a tunnel under Breakneck Ridge. Proceed for another 0.3 mile and park in a small parking area on the right (east) side of the road, just before a small blue "adopt a highway" sign.
Train Directions
Take the Metro-North Hudson Line to the Cold Spring station and walk north on Route 9D to the trailhead. Find link for info here
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Hike Description
At the parking area, you'll see a triple-yellow blaze that marks the start of the Wilkinson Memorial Trail, which you will follow for the first half of the hike. The trail begins to climb on a winding woods road, passing a stone foundation to the right. In 0.2 mile, the green-blazed Nimham Trail begins on the right, but you should continue to follow the yellow-blazed Wilkinson Memorial Trail. After about a third of a mile, the trail briefly leaves the road to cross a stream. The climb back to the road is rather steep, but the grade moderates when the trail turns left and rejoins the road.
About 0.6 mile from the start, the red-on-white-blazed Breakneck Bypass Trail begins on the right. This will be your return route, but for now, continue ahead on the yellow-blazed Wilkinson Memorial Trail, which soon turns left and descends slightly to cross a stream.
The trail now begins to climb Sugarloaf Mountain on switchbacks. (Due to ecological considerations, the trail has been rerouted and no longer continues to the summit of the mountain.) After a steep section, the grade moderates. Before reaching a very steep section, the trail turns right and levels off in a wooded area that was once farmed, passing a moss-covered stone foundation at the lowest point. After crossing a woods road and several seasonal streams, the trail bears right and begins to parallel the aptly-named Cascade Brook, climbing steadily but gently.
After paralleling the brook for a quarter mile, the trail turns left, crosses the brook and a woods road, and begins a much steeper climb. On the way up, it comes out on open rocks, with the highest point on Breakneck Ridge visible to the right. Soon afterwards, the trail levels off along a minor ridge, then climbs steeply to another viewpoint (just to the left of the trail) at the summit. The elevation here is 1,220 feet, and this is the highest point you'll reach on this hike. From here, you can see the Newburgh-Beacon Bridge, Dennings Point and the city of Beacon (on the east side of the river).
As you descend from the summit, you'll pass another viewpoint over the river and soon reach a junction with a woods road. Turn right, leaving the yellow-blazed Wilkinson Memorial Trail, and follow the green-blazed Connector Trail. In a short distance, you'll come to another trail junction, where you should again turn right, now following the white-blazed Breakneck Ridge Trail.
Continue to follow the joint Breakneck Ridge Trail for over a mile. For most of the way, the trail is relatively level, although there are some ups and downs. After about a mile, the trail makes several short but steep descents, then begins a steady, steep climb. On the way up, the blue-blazed Cornish Trail branches off to the left, but you should continue to follow the white-blazed Breakneck Ridge Trail. A short distance beyond the junction, there is a view over Surprise Lake (and the youth camp located along the lake) from open rocks to the left of the trail.
At the top of the climb, you'll reach a 360-degree viewpoint - perhaps the most panoramic of the entire hike. You can see both north and south along the Hudson River (with the eastern section of Breakneck Ridge blocking the view in between), Bull Hill to the southeast, and Surprise Lake to the northeast.
The trail descends very steeply from the summit, then levels off. Keep a lookout for three red-on-white blazes on a large boulder to the right of the trail. These blazes mark the start of the Breakneck Bypass Trail (blazed with both red and red-on-white markings).
Turn right, leaving the Breakneck Ridge Trail, and follow the Breakneck Bypass Trail, which climbs a small rise. As you descend from the rise, watch carefully for a sharp left turn in the trail after 100 feet, marked with a double blaze on a rock and on a nearby tree.
Soon, you'll reach a viewpoint to the right of the trail, looking northeast over Sugarloaf Mountain, with the Newburgh-Beacon Bridge in the distance. Continue to descend along an eroded woods road, with the trail having been rerouted to the left to avoid some badly eroded sections. After turning sharply right and leaving the road, the trail climbs slightly to another view of Sugarloaf Mountain - this one, at a closer range.
From this final viewpoint of the hike, the Breakneck Bypass Trail descends - first steeply, then more gradually - and it ends at a junction with the yellow-blazed Wilkinson Memorial Trail. Turn left and retrace your steps, descending along the Wilkinson Memorial Trail for 0.6 mile to your car on Route 9D.