Sunday, August 17, 2025

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

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