Lemon Squeezer / Island Pond Loop


This loop hike climbs to the summits of Green Pond and Island Pond Mountains, goes through the narrow Lemon Squeezer, and passes the historic Boston Mine.

4.5 hours
Moderate to Strenuous
7.5 miles
Route Type:
Allowed on leash
Views, Public Transportation
First Published:

Daniel Chazin


Lemon Squeezer Trail  / Island Pond - Harriman State Parks.


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Trail Conference volunteers maintain trails in this park.
Trailhead GPS Coordinates
Driving Directions

Take N.Y. Route 17 north through Sloatsburg, Tuxedo and Southfields. About two miles north of Southfields, turn right onto Arden Valley Road. Cross the bridge over the New York State Thruway, then make the first right at a sign "Hikers' Trailhead Parking." Park in the dirt parking area to the west of a large meadow, known as the Elk Pen.


Take Shortline bus from Port Authority. Buy tickets to Southfields (round trip hikers discount of course), and ask the bus driver to let you off at Arden Valley Road next to a "Welcome to Harriman State Park" sign & a sign with a drawing of two hikers (a couple of miles north of the old Red Apple Rest).  Return bus stops across the street - wave the driver down.  After you get off the bus, make a right onto Arden Valley Rd., walk across the bridge over the NY State Thruway, then notice two white A.T. blazes under a sign that says "Rough Road next 5 miles ahead" indicating to turn into the woods.  This takes you to a parking lot and on the other side of the lot slightly to the right, the trail continues through a field, then makes a right onto a woods road to an A.T. mile marker sign for Lemon Squeezer and other destinations.


From the parking area, follow an unmarked woods road east across the meadow. At the end of the meadow, you will notice three red-triangle-on-white blazes, which mark the start of the Arden-Surebridge (A-SB) Trail. Turn right and follow the A-SB Trail south for about 100 feet, where you will see a wooden sign giving mileages along the Appalachian Trail (A.T.). You will be following the A.T., marked with white blazes, for the next two and one-half miles of the hike. Turn left onto the A.T., which begins a steady ascent of Green Pond Mountain, first moderately, then more steeply. After a climb of over 500 vertical feet, you'll reach the summit of the mountain, where a large boulder to the left of the trail affords limited views to the west. The A.T. now descends the eastern slope of the mountain on switchbacks.

At the base of the descent, follow the A.T. as it turns left onto Island Pond Road, a dirt road built by Edward Harriman (after whom the park is named) about 1905. You'll soon enter a beautiful hemlock grove. After only about 500 feet on Island Pond Road, the A.T. turns right, goes over a small rise, and crosses a gravel road built in the 1960s to provide access for fishermen to Island Pond. The trail descends to cross an outlet of the pond on a small wooden bridge. The stone spillway you see was built by Civilian Conservation Corps workers in the mid-1930s as part of a plan to increase the size of Island Pond by damming it. The work was never completed, though, and the pond remains in its natural state.

The A.T. now ascends to a knoll overlooking beautiful Island Pond. On the way, you will pass a large rusted metal object to the right.Gravel Sorter at Island Pond. Photography by Stephen Harris This was a rotary gravel sorter, used to separate different sizes of gravel. The trail then descends and turns right on another woods road, known as the Crooked Road. After a short distance, the white blazes leave to the left and climb to a junction with the A-SB Trail, marked with red triangles on a white background. Turn left at the junction and follow the joint A.T./A-SB to the base of a large rock formation, where the two trails split.

This rock formation, known as the Lemon Squeezer, is one of the mostLemon Squeezer. Photography by Stephen Harris interesting features of the park. Turn left and follow the A.T. as it climbs through a very narrow passage between the rocks and then goes up a steep rock face, where you will need to use both your hands and your feet. Those who are physically able to negotiate these challenges will find them to be a highlight of the hike. But if the climb is too difficult, it is possible to bypass the Lemon Squeezer by following a path to the left.

After reaching the top of the Lemon Squeezer, the A.T. continues on a more moderate grade to the summit of Island Pond Mountain. The stone ruins just north of the summit are the remains of a cabin built by Edward Harriman. This is a good place to stop and take a break.

The A.T. descends from the mountain and enters an attractive hemlock grove. After winding through the hemlocks, you will reach a junction with the aqua-blazed Long Path, marked by a wooden signpost. Turn right, leaving the A.T., and follow the Long Path as it skirts the edge of Dismal Swamp. The ridge visible across the swamp to the east is Surebridge Mountain. A short distance beyond a wet area, crossed on tree roots, you will come to a woods road -- the route of the A-SB Trail (now encountered for the third time). Cross the road and bear left, where you will see three horizontal white blazes, marking the start of the White Bar Trail. Continue ahead on the White Bar Trail, which briefly joins a woods road, then turns left on a wider woods road - the continuation of the Crooked Road that you followed earlier in the hike.

After about a mile on the White Bar Trail, the yellow-blazed Dunning Trail joins from the left. Continue ahead, now following both white and yellow blazes. When the two trails separate a quarter of a mile later, turn right and follow the yellow blazes of the Dunning Trail. After passing a large cliff to the right, the trail ascends a rise, then descends to the base of the Boston Mine. This iron mine -- a large open cut into the hillside, partially filled with water -- is reached by a short path to the right. It was last worked around 1880.

After visiting this mine, continue ahead on the yellow-blazed Dunning Trail. In 500 feet, you will reach a wide woods road - the southern extension of Island Pond Road. Turn right, leaving the yellow-blazed trail, and follow unmarked Island Pond Road as it descends through hemlocks and laurels towards Island Pond. When you once again encounter the red-triangle-on-white blazes of the A-SB Trail, continue ahead, bearing right at the fork. At the next Y-intersection, again bear right, and you will soon arrive at the ruins of a stone building, built by the park as a ranger station. Just beyond, a rock ledge affords an expansive view over scenic Island Pond. This is a great spot to rest and take a break.

When you are ready to continue, retrace your steps along the road to the junction with the A-SB Trail. This time, bear right and follow the A-SB as it heads west, crossing a swamp and the southern outlet of Island Pond. A short distance beyond the swamp, turn left, leaving the road, and follow the red-triangle-on-white blazes across the southern end of Green Pond Mountain. You'll pass through an area with many dead trees, where there are good views to the west. Just beyond, the trail begins a steep descent on switchbacks. The grade soon moderates, and after about a mile on the A-SB, you'll reach a grassy woods road - the Old Arden Road - at the base of the descent. Here, the red-on-white blazed Stahahe Brook Trail begins to the left, but you should turn right and continue to follow this A-SB Trail northward along the road to its terminus, marked by a triple-blaze. Turn left and follow the woods road across the meadow back to the Elk Pen parking area, where the hike began.

Comment: Please be relevant, civil, non-commercial.

Reverse hike/swimming access?

Is there any recommendation against doing this hike in reverse?  I was hoping to stop for a swim in Island Pond near the end of the hike, and I believe the boat launch/swimming area is on the north end of the pond, so in order to pass by there near the end of the hike, I'd have to do this loop in reverse.  Has anyone tried this?  Is it dangerous to go through Lemon Squeezer from the other direction?

Great day in Early October 2015

Did this hike on a beautiful early fall day in October. Weather was perfect - leaves just starting to change. I've done at least 6 Moderate to strenuous hikes in W. Harriman - this is one of the better ones. Directions are spot on if you pay attention. Lots of features: iron mine, abandoned structures, great pond surrounded by colors, swampy wetlands, and varied terrain. No real hard climbs and one pretty steep down hill. The distance was good for 4.5 - 5 hours if you minimize breaks < 1/2 hr total. Foot traffic was not so bad for Harriman. I could sometimes go for an hour or more without seeing anyone. This is a good one to do.

Island Pond looks like a Bob Ross Painting now!

Nothing at all to complain about this hike. Very well marked and easy to follow. There were lots of hikers out yesterday. Island Pond is a fantastic place to spend a few hours, especially now with all the colors!

Long Path by Dismal Swamp

Great hike with varied terrain. We came across a deer skeleton on the Long Path just as we entered Dismal Swamp. The skeleton was completely intact, clean and placed directly in the middle of the trail. Would coyotes do something like that? It was an eerie sight to see just before entering the swamp section. Very happy to come to the junction with the A-SB. 

this is a great place to get lost - twice

"When you once again encounter the red-triangle-on-white blazes of the A-SB Trail, continue ahead, bearing right at the fork. At the next Y-intersection, again bear right, and you will soon arrive at the ruins of a stone building, built by the park as a ranger station."  The A-SB trail is very poorly marked in this area, and you can probably skip this excursion to the ranger station, so that you don't wind up getting lost and hiking on Island Pond Road all the way back to the A-T, which then takes you the long steep way around to get back to Elk Pen.  Just saying...

I decided to spend Easter in

I decided to spend Easter in nature's cathedral and do a hike on the AT/Lemon Squeezer loop which is a good hike with plenty of variety.  The trees were still pretty bare when I did this hike but I imagine that it would be very beautiful in the summer and the fall.  I would recommend this hike.  It was beautiful and not strenuous at all.  I walked it slowly and completed it in four hours.  The description/instructions above are easy to follow and are exact to keep you on the right path and keep you informed on what's coming up next.  Also I took public transportation to reach the trial and it couldn't of been easier.  It was exactly as the bus instructions suggest.  When I got on I told the bus driver where I wanted to get off and he didn't bat an eye at my request and dropped me right off at the parks enterance.  Coming back to NYC was just as easy.  I stood on the oppisite of the road and when I saw the bus come around the bend I just waved at the driver and he stopped right in front of me and picked me up.  I would recommend that you look up the bus schedule so you know when the bus is coming back so you can be out on the road on time and not too early or too late.  The best thing is when you get your round trip ticket at the Shortline bus ticket booth in the Port Authority make sure you tell them that you are hiking and they will give you a hikers discount. Enjoy the trail. 

Hiking the AT/Lemon Squeezer

Instead of the mall on Black Friday, I took the  AT/Lemon Squeezer loop...  a good hike.  The only caution was the slippery leaves on the trail...   the views and scenery ... excellent.  I can imagine this is best in the Fall at peak! Alas, since I was hiking solo, I was unable to scale the rock face near the Lemon Squeezer. I would have like to see this accomplished!  This hike has it all - forests, steep climbs, rock formations, Island Pond, Dismal Swamp...   recommended. View my images  : http://www.flickr.com/photos/ sph001/sets/72157628207656729/ show/ Read my thoughts on this trail : http://www.taking-a-hike.com

Your hiking photos

Excellent pictures of this Harriman classic.