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

Mount Frissel Tri-State Hike

Mount Washington State Park, MA
Taconic State Park, NY

Hiking Trails:
Mt. Frissel Trail: Red blaze

Total Time: 3:00 hour
Estimated Distance: 2.9 Miles

Pros: Good climb, excellent views, landmark area
Cons: None
Hike Type: Back and out
Level of Difficulty: Very difficult

Google Maps of Parking:
https://maps.app.goo.gl/nJaVMvAAbcM6Vgi88

Hiking Partners:
Yehudah Koblick

Continuing along our camping trip in Taconic State Park, we went on this hike on Mount Frissel which transverses the highest point in Connecticut, as well as the tri-state mark of New York, Massachusetts, and Connecticut. The peak of Mt. Frissel is not in Connecticut but in Massachusetts, but the main view is a bit below the summit and in Connecticut. 

We parked at the state line on East St/Mt. Washington Road, and took the Mt. Frissel Trail west up Round Mountain. This route up was very steep and difficult, but there was a good view on the top. We then continue along the trail, dipping down and then steeply up again as we ascending Mt. Frissel. After reaching the summit, in Massachusetts, we descending slightly to cross the state line into Connecticut with the great view. We then continued to the tri-state line and then turned around and came back the same way.

Map of the Route

Obelisk at the Connecticut/Massachusetts State Line at the Parking

Mt. Frissel Trialhead

Ascending Round Mountain

Round Mountain View

View of Mt. Frissel

View from the Mt. Frissel View on the Highest Point of Connecticut

Rock Pile at the State Line and Highest Point

USGS Marker

State Line Obelisk (NY, CT, MA)

NY Side of the Obelisk (Strangely, CT is missing an engraving)

Old Stone Obelisk on the Floor at the State Lines

Back at the Mount Frissel View