The Lemon Squeezer Loop at Harriman State Park is a popular trail that traverses the Appalachian Trail (AT) and the New York Long Path (Long Path) and circles Island Pond. The enormously popular Harriman State Park features a train stop, making it one of the most accessible state parks from New York City. The entire park is maintained by the NY-NJ Trail Conference. The following epic trail is 7.6 miles—with total elevation gain of 1,360 feet—and can be completed in five hours.
The Lemon Squeezer Loop starts at Elk Pen Trailhead with an open meadow. Walk toward the tree line and you will find the famous white blaze of the AT, which runs continuously from Georgia to Maine. But on this excursion, you can enjoy a small section of the trail as it leads to an awesome geological formation.
Follow the AT toward a gradual incline into the forest, where a sign will give mileage to the Lemon Squeezer and other points of interest. Take note of Green Pond Mountain, Island Pond, and, of course, Lemon Squeezer since they will all be a part of your journey. Now it’s time to begin the climb toward Green Pond Mountain.
The ascent to Green Pond Mountain is the steepest climb of the hike, but it’s gradual and of an easy grade. This entire leg of the trail is tree-covered, but during winter or late fall hikes there are amazing views. There is a switchback early on in the climb that is often missed—it looks like the trail continues straight up the mountain. However, the trail actually cuts to the right and continues up slowly, but surely. Once you reach the man-made stairs, you have reached 1,000 feet in elevation.
At the summit of Green Pond Mountain there are massive boulders. Be sure to check out the boulder to the left that can be climbed for views of western mountain ranges and Sterling Forest State Park.
After taking in the views of Green Pond Mountain, the descent to Island Pond begins. The trail gradually declines and—on leafless days—Island Pond is visible in the distance. The descent curves right and then left before intersecting with Island Pond Road, which you can take if you want to sit near the water, just note, that there are better views available further along the AT.
Continuing on the AT you will arrive at a stream with a bridge. On the right there is a small unmarked trail with a sign that reads, “Fires Not Permitted.” Follow this trail for a great view of Island Pond.
Once back on the AT, the trail will climb then descend over a stream until you reach a huge rock formation that is home to the Lemon Squeezer. There is also a trail junction between the AT and the Arden-Surebridge Trail, marked with a red blaze. This formation marks the beginning of the ascent of Island Pond Mountain.
Follow the white blaze under a large rock formation of a large boulder sitting on top of another. Enter the Lemon Squeezer’s three foot high by one foot wide path. The weird angle adds to the entertaining maneuvers involved with traversing through it.
Right after finishing the Lemon Squeezer, there’s another rock formation that must be climbed to continue along the trail. Luckily, there’s a tree that grows in the rock and its roots can be of great assistance getting up and over. Don’t worry, if you don’t want to make the climb, there’s an easy route around the challenge; it’s marked with a sign post reading “Easy Way.” But if you are wavering, just remember, it’s way more fun going the “hard way.”
After the climb, the trail continues ascending toward the summit of Island Pond Mountain and opens up to grassy area. The AT continues over the summit and down into a pine tree grove until coming to another signpost marking a junction with the Long Path. The Long Path runs from the George Washington Bridge to the Adirondack Mountains. Take a right onto the Long Path with the green blaze toward the White Bar Trail.
The Long Path descends toward an area known as the Dismal Swamp. The swamp is a wet area, and Gore-Tex is an asset here. You’ll want to be wearing something from La Sportiva (like the Trango TRK GTX)—you can find their line at REI—to make it through the cattails and other swamp flora with dry feet.
The trail continues until reaching an intersection with the Arden-Surebridge Trail. Many hikers take the Arden-Surebridge Trail back to the AT then retrace the the trail to Elk Pen. You can also take a left onto the Arden-Surebridge Trail for less than a minute before turning right to the White Bar Trail.
The White Bar Trail is less maintained than the AT or Long Path, and it has rugged terrain, but no major incline or decline. There is also less traffic along the White Bar, just be careful not to lose the blaze as switchbacks are common.
The White Bar Trail merges with the Dunning Trail, marked with a yellow blaze. The two trails continue through rugged terrain along a narrow path, and cross over streams and rock formations. Make a right where the Dunning Trail makes a hard break from White Bar toward Green Pond and the Valley of Boulders. The yellow blaze will drop off on the right from the white blaze.
The Dunning trail will pass a large boulder that seems like an excellent bouldering spot if you could get a mat this far into the state park. Soon after, Green Pond will be visible on your left. The Dunning Trail will then intersect with the Nurian Trail, which is marked with a white blaze. Bear right onto the white blaze and soon the trail comes to a scenic view of the southeast.
It is now that you will begin your descent into the valley of boulders, which features waterfalls and many different rock formations. This area has remarkable scenery and gets little traffic.
Once through Valley of Boulders, the final leg of your journey begins. The Nurian Trail intersects with the Stahahe Brook Trail, marked with a red blaze. The trail leads back to the Elk Pen Trailhead and features a very scenic mossy area along the Stahahe Brook. After reaching what looks to be the remains of a bridge, the trail turns right and acts as a dividing line between open fields to the left and the forest to the right until reaching the trailhead.
The Lemon Squeezer trail is fun for its variety of terrain and beautiful scenic viewpoints. It’s a great adventure that can be adjusted to reach the many shelters of Harriman State Park. It also takes advantage of the AT and Long Path at one of the few places where the two popular thru hikes meet.