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.

5 hours
7 miles
Route Type:
Allowed on leash
Views, Public Transportation
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Daniel Chazin
Trail Conference volunteers maintain trails in this park.
Trailhead GPS Coordinates
Driving Directions

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.Hudson River from the summit Sugarloaf Hill. Photo by Daniel Chazin.

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.

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Directions from the train

If you are taking the train to Garrison and do not have a detailed map, this is the most direct route to the start of the trail: - Find the stone pillars (marked Arden Highlands) at the southern end of the train station parking area - Follow that trail (blue markers) passing over a narrow wooden bridge and then coming to a metal bridge over the tracks. If you continue straight at that junction (and do not take the bridge) you will be on a white trail that will bring you to the Garrison Institute (0.5 - 1 mile to Garrison Institute from the train station) - You can get to the main road by walking up the stairs and around the side of the main Garrison building and follow the Garrison driveway to the main road, Route 9D.  (this was not a problem when we did it and Garrison has many hiking trails in the woods surrounding it) - Walk right (south) on Route 9D for 300 feet to Wing and Wing Drive (two more stone pillars) then go left thru the pillars and you will be on the Driving directions above.  Follow the road towards the parking area then see the directions above. (If anyone knows of a route to avoid walking through Garrison Institute please update these directions for those taking the train)

Watch for ticks and turns!

I did some trail running on the Osborne Loop yesterday, and wanted to point out two things: 1- When you're headed north after leaving the Appalachian  Trail, you will come to a sharp left turn after about a mile and a half. Stay alert, as this turn is blazed with only a single blaze, and can be confusing. I believe this is the point in the hike description above where it says "after climbing to a viewpoint over the Hudson River". The turn is right before you make that climb, and needs to be blazed as a turn. 2- I found a tick on me this morning, so if you hike this trail, check yourself well after you are done. There are lots of spots where the trail needs to have branches trimmed.

Prickly Pear Cactus

When you reach the top of Sugarloaf Hill please be careful to not step on the prickly pear cactus. In the NY area it is not uncommon on southfacing rocky outcrops. Even though most people think of it as a desert plant it is found in almost all states and not necessarily in a desert enviroment, though typically dry.

More about how to do it from the train

See for more information about the trails from the train station parking lot.

Slight changes

Just did this hike today, and now there is a path right from the parking area through the field to the woods road. When you reach the woods road, go right, and you will pass the gazebo in a few hundred feet. keep going and you will be on the red blazed trail. Also, for those taking the train to Garrison, stay alert. I took the trail that begins at the station and came out on the Garrison Institute grounds, and had to walk a bit to get to 9D. Once there though, the Castle Rock Unique area entrance was right across the street :)

Sugarloaf trail

Just to follow up on Michael K7 re the alternate start: From the parking area, you can look for the blue "New York Department of Environmental Conservation" blazes. These will take you maybe 100 yards, past a red pumphouse and up to the beginning of a field. Follow the tire tracks across the field toward Castle Rock and into the woods. You will come to the carriage road about 20 yards into the woods, and it is not marked in either direction. Make a right onto the carriage road, which parallels the top edge of the field, and it will take you to meet the official (red-blazed) trail at the gazebo, as Michael said. This is more pleasant than walking back along the road to the official trailhead, and I saw no markers discouraging the use of this route.

Fire at Castle Rock Unique Area

A brush fire on March 24, 2009 burned approximately 50 acres on the west face of Sugarloaf Mountain in the Castle Rock Unique Area. Firefighters brought the fire under control before it spread more widely. They suspect a discarded cigarette was the cause. The Red Trail that ascends the mountain from the west passes through the area that burned.