Island Pond, Lemon Squeezer, AT, & Long Path

Harriman State Park
Rockland Co, NY

Hiking Trails:
Crooked Road Path: Unblazed
Appalachian Trail: White blaze
Long Path: Green blaze

Total Time: 2:05 hour
Estimated Distance: 3.8 Miles

Pros: Scenic lake, rock formations, good view, and quiet area
Cons: Crooked Road Path overgrown
Hike Type: 2 car point to point
Level of Difficulty: Difficult

Google Maps of Parking:
Car 1: https://maps.app.goo.gl/TqJ4eS9tjwm5qEV58
Car 2: https://maps.app.goo.gl/asNNz2gSPdHMmhz38

Hiking Partners:
Jacob Baldinger

We parked on Island Pond Road at the Crooked Road Path. We took the Crooked Road path to the Appalachian Trail. This trail was very overgrown and not properly maintained. Upon reaching the Appalachian Trail we went down to the Island Pond, and then turned back to the Appalachian Trail and headed to the Lemon Squeezer, a rock formation with covered rock and narrow pathway through the rocks.

After the Lemon Squeezer, we climbed up Island Pond Mountain and took a short bushwhack to the view above the lake, and then continued down the mountain to intersection of the Long Path and Appalachian Trail, the two most famous hiking trails in New York. We then took the Long Path to the unmaintained shelter, then past Surebridge Swamp, and then to Arden Valley Road where the other car was located.

Map of the Route

Overgrown Crooked Road

Island Pond

Lemon Squeezer

Island Pond Mountain

Appalachian Trail on Island Pond Mountain

AT / Long Path Intersection

View Approaching the Unmaintained Shelter

Unmaintained Shelter

Surebridge Swamp

Surebridge Mountain Loop

Harriman State Park,
Orange Co.,
New York

Hiking Trails:
Crooked Road: Unblazed
Arden-Surebridge Trail: Red blaze
White Bar Trail: White blaze
Dunning Trail: Yellow blaze
Surebridge Mountain Trail: Unblazed
Lichen Trail: Blue blaze
Long Path: Green blaze
Appalachian Trail: White blaze

Total Time: 2:00 hour
Estimated Distance: 4.2 Miles

Pros: Great views, scrambles, and interesting rock formations
Cons: None

I had hiked nearby this area the previous week, and had wanted to go back to the higher terrain of Harriman between Kanawauke Road and Arden Valley Road that is highly exposed with large, barren rock faces. This area is exceptionally scenic, especially during the fall with the bright foliage.

I parked on Arden Valley Road at Crooked Road, and took the Crooked Road path past the Appalachian Trail and to the Arden-Surebridge Trail. I then took the Arden-Surebridge Trail for a short distance, and then cut across to the White Bar Trail, which I took south until the Dunning Trail.

I took the Dunning Trail west, as it climbed up Surebridge Mountain. I then cut across on a bushwack on a somewhat used route to the rocky exposed area where there is an outstanding view facing west. Most of the area of Surebridge Mountain from this point is formed of large, exposed bedrock and short shrubs, with continuos views to the west. I noticed an informal path at this point going North near the escarpment of Surebridge Mountain. The path has red strings tied to strings and cairns (rock piles) along the route. I took this newly discovered trail north until right before it ends, where I bushwacked over to the Lichen Trail.

I took the Lichen Trail to north to the big rock exposure on that trail, and the view overlooking Island Pond. I continued along this short trail to it terminus at the combined Arden-Surebridge Trail and the Long Path, going west towards Island Pond. I continued along the Arden-Surebridge Trail where it split with the Long Path, and then went passed the Lemon Squeezer, where I met up with the Appalachian Trail. I took the Appalachian Trail for a short distance back to Crooked Road, which I took back to my car.

Map of the Route

Crossing a Saturated Brook on the Arden-Surebridge Trail

Surebridge Mountain Summit

Rocky Area along the Surebridge Mountain Summit

View from Surebridge Mountain Facing Southwest

View from Surebridge Mountain Facing Northwest

Same View, Zoomed in to Island Pond

View Facing West

Large Pine Tree on Surebridge Mountain

Cairns along the Unofficial Surebridge Trail

Large Rock on Surebridge Mountain

More Rocks on Surebridge Trail

Fall Foliage Colors along the Rocks

Me at the Ramapo-Dunderberg and Lichen Trail Intersection

Me at the Same Location Above

Lichen Trail

Island Pond from the Lichen Trail

Zoomed into Island Pond

Large Rock Approaching the View on the Lichen Trail

Lichen Trail Rock

Lemon Squeezer Entrance that I Passed

Island Pond Mountain and the Lemon Squeezer

Island Pond Mountain and the Lemon Squeezer
Harriman State Park,
Orange Co.,
New York

Hiking Trails:
Crooked Road: Unblazed
Appalachian Trail: White blaze
Appalachian Trail Bypass: Blue blaze
Island Pond Road: Unblazed

Total Time: 1:30 hour
Estimated Distance: 2.3 Miles

Pros: Great scramble and rock formation, nice views, and scenic lake
Cons: Parking can be challenging

Hiking Partners:
Rayzi Friedman
Joseph Friedman

The Island Pond area is one of my favorite areas in Harriman State Park. It's a remote and very scenic area of the park. We parked on Arden Valley Road on a small pull-out near Crooked Valley Road that I am familiar with. (There is official parking available directly by Island Pond if you purchase a key to the area from the State Park office at Lake Tiorati.)

We took Crooked Valley Road, which is an unmarked path that extends from Arden Valley Road to the Appalachian Trail. We then took the Appalachian Trail east, and at the intersection with the A-SB Trail, we went through the Lemon Squeezer and then climbed up Isand Pond Mountain. above the Lemon Squeezer. To the east of the trail there is a beautiful view towards Monroe and Island Pond to the south.

We then climbed back down through the Lemon Squeezer, took the Appalachian Trail towards Island Pond, and cut at one of the paths down to the lake for a nice view of the lake. We then cut back to the Appalachian Trail, took Island Pond Road back to Arden Valley Road, and walked along the side of Arden Valley Road back to our car.

Map of the Route

Approaching the Lemon Squeezer.
Note the People on the Trail in the Distance

Boulder Tunnel at the Entrance to the Lemon Squeezer

Me in the Lemon Squeezer

Rocks of the Lemon Squeezer

Narrow Path inside the Lemon Squeezer

Rock Overhangs in the Lemon Squeezer

Me under a Rock Overhand in the Lemon Squeezer

Steep Trail Ascent near the end of the Lemon Squeezer

View from Island Pond Mountain, Facing Northwest

Me on Island Pond Mountain

Island Pond in the Distance from Island Pond Mountain

Another view of Island Pond from Island Pond Mountain

View from Island Pond Mountain, facing Southwest

Rock Formation Jutting into Island Pond

Me at Island Pond

Island Pon d