Sugarloaf Hill and Osborne Loop

Hudson Highland State Park,
Putnam Co.,
New York

Hiking Trails:
Blue Trail: Red blaze
Sugarloaf Trail: Red blaze
Osborn Loop Trail: Blue blaze
Appalachian Trail: White blaze

Total Time: 3:15 hour
Estimated Distance: 7.6 Miles

Pros: Good view
Cons: Quiet remote area with little traffic
Level of Difficulty: Moderate

It had been a while since I did a long hike. Now with my big trip and the summer behind, I took the opportunity to do this longer loop on some new trails for me. I had been to Sugarloaf Hill before, as well as parts of the Osborn Loop, but the last time I was at Sugarloaf Hill was in 2011, and I have been intent on covering more trails in Hudson Highlands State Park in the eastern Hudson Highlands.

I parked at the trailhead at Wing and Wing Road, where the Blue and Sugarloaf Trails start. The Blue Trail probably has a name, but its not listed on the map. Its a short trail going through the grassy meadow, and then ending at the Sugarloaf Trail. I took the Blue Trail to the Sugarloaf Trail, which climbs up to the top of Sugarloaf hill as a dead end at the top. Sugarloaf is a prominent mountain jutting out from above the Hudson, and the top forms a narrow ridgeline. At the dead end of the trail there is a view facing south to the Bear Mountain Bridge, and a large cactus grove.

I turned around at the end of the Sugarload Trail, and then took the western portion of the OSborn Loop southward, all the way down to its terminus at the Appalachian Trail. I then took the Appalachian Trail northbound, back to the Osborn Loop, which I took south and then west, back to the Sugarloaf Hill Trail. I then took the Sugarloaf Hill Trail down the mountain, through the grassy field, and back to my car.

Map of the Route.
East Hudson Highlands.

Blue Trail through the Meadow

Barns Along the Trail in the Meadow

Leaving the Meadow and Going into the Woods
and the Foot of the Mountain

View of West Point

View of West Point, Zoomed Out

Narrow Ridgeline at Sugarloaf Hill

View at Sugarloaf Hill, Facing South Zoomed Out

View South from Sugarloaf, Facing Hudson River and Bear Mnt. Bridge

View from Sugarloaf Hill, Facing East

Cactus Grove at Sugarloaf

Lots of Trail Markers at Osborn Loop Intersection with Sugarloaf

Horses at the Above Intersection

Appalachian Trail

View Along the Appalachian Trail

Early Foliage along the Appalachian Trail

Sugarloaf Hill from the Meadow along the Sugarloaf Trail

Castle in the Distance Across the Meadow near the End of the Hike

Appalachian, Carriage Connector & Osborn Loop

Hudson Highlands State Park
Putnam County,
New York

Hiking Trails:
Appalachian Trail: White blaze
Carriage Connector Trail: Yellow blaze
Osborn Loop Trail: Blue blaze

Total Time: 2:20 hour
Estimated Distance: 3.9 Miles

Pros: Remote and scenic area
Cons: Views are limited

I wanted to go a bit further north so I could still get some snow in the hike. The snow was still present along most of the hike, but was melting and left things very wet. I parked on Cross Road between Route 403 and Route 9 right near the Appalachian Trail. I walked the short distance south on Route 403 to the Appalachian Trail. The beginning of the hike features a boardwalk going over a swamp area, and the boardwalk is quite dilapidated and in need of repairs.

I continued along the Trail as it climbs the mountain gradually in a scenic valley beside a stream. At the trail intersection of the Carriage Connector Trail, I continued in the same direction along Carriage Connector Trail climbing the the valley until the trail headed east and then intersected the Osborn Loop by a small pond. All along the route, I was very much enjoying the dense greenery of the evergreen mountain laurels and hemlocks, especially in contrast with the snow.

I continued up the Osborn Trail to the highest part of the trail, which unfortunately featured no view. Right after the high point, I reached the Intersection of the Appalachian Trail, which I took down the mountain to where it connects to the Carriage Connector Trail. At this point realizing I still had a bit of time, I bushwacked up the hill up ahead which showed a view on the map, labelled as "White Rock." I climbed the steep ascent to the view, and on the top I noticed that one of the gloves that I had placed in my pocket was missing. I therefore opted to take the same route down the hill so I can trace the route, and actually found my glove right at the bottom at the intersection of the Appalachian and Carriage Connector Trails. I then took the Appalachian Trail back to my car.