Iron Mines Loop #3 (Northwest/Lemon Squeezer)


This loop hike traverses the ridge of Surebridge Mountain, passes by the historic Greenwood and Surebridge Mines and climbs through the narrow Lemon Squeezer.

5 hours
Moderate to Strenuous
7 miles
Route Type:
Allowed on leash
Views, Historic feature
First Published:
Daniel Chazin


The Lemon Squeezer


View Tiorati Parking in a larger map

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

Take N.J. Route 17 north to the New York State Thruway and take the first exit, Exit 15A (Sloatsburg). Turn left at the bottom of the ramp onto N.Y. Route 17 north, and continue through the Village of Sloatsburg. Just past the village, turn right at the traffic light, following the sign for Seven Lakes Drive/Harriman State Park. Cross an overpass over railroad tracks and continue along Seven Lakes Drive for about 10 miles to the Tiorati Circle. Go 270° around the circle and proceed west on Arden Valley Road. Almost immediately, turn left into the Tiorati parking area. A parking fee may be charged in the summer.


Towards the southern end of the parking area, you’ll notice a triple blue blaze, which marks the start of the Lake Tiorati Trail. Proceed uphill on this trail to the ridge of Fingerboard Mountain, following the old route of Arden Valley Road for part of the way. At the top, turn left on the joint Appalachian Trail (A.T.) (white)/Ramapo-Dunderberg (R-D) Trail (red dot on white), which follows a woods road past a concrete water tower and continues to climb along the ridge of Fingerboard Mountain on a footpath. You’ll reach a few false summits, one of which features an interesting balanced boulder. When the leaves are down, Lake Tiorati may be seen through the trees on the left.

About a mile from the start, you’ll reach a junction marked by wooden signs. Here, the blue-blazed Hurst Trail begins to the left. This trail leads down a few hundred feet to the stone Fingerboard Shelter, built in 1928. You may wish to take a short detour to check out this shelter, at which overnight camping is permitted.

Continue south on the joint A.T./R-D, which soon reaches another intersection. Here, the Appalachian Trail turns right, but you should follow the red-on-white blazes of the R-D Trail, which continues ahead along the ridge. The R-D Trail passes through attractive thickets of mountain laurel and hemlock. After reaching an open area, the trail descends rather steeply. At the base of the descent, watch carefully for the crossing of the Bottle Cap Trail, with its unique blazes – white bottle caps nailed to the trees.

Turn right onto the little-used Bottle Cap Trail, which traverses interesting terrain. Soon, you’ll notice a water-filled pit to the right of the trail, with a pile of mine tailings (discarded pieces of rock) just beyond. These are remnants of the Surebridge Mine, which was active during the Civil War. A short distance beyond, you’ll notice the remains of a banked stone structure to the left. More mine pits may be found to the south. For more information on this and other mines in the area, consult Ed Lenik’s book Iron Mine Trails.

The Bottle Cap Trail descends to cross the unmarked Surebridge Mine Road (the intersection is marked by a cairn) and, just beyond, Surebridge Brook. This crossing can be a little tricky if the water is high, and you may have to go a short distance upstream or downstream to find a good place to cross. After climbing steeply to the ridge of Surebridge Mountain, the trail bears left and overlooks the Surebridge Swamp, with Hogencamp Mountain visible In the distance beyond.

The Bottle Cap Trail descends through a dense hemlock forest, joins a woods road and ends at a junction with the joint aqua-blazed Long Path and red-triangle-on-white-blazed Arden-Surebridge (A-SB) Trail. Continue ahead on the woods road, now following the joint route of these two trails. In 300 feet, after crossing a wet area on rocks, the White Bar Trail leaves to the left. Just beyond, both the A-SB Trail and the Long Path turn right, leaving the woods road, and diverge. Continue on the A-SB Trail (red triangle on white), which takes the left fork.

Soon, you’ll notice a dramatic cleft at the edge of a cliff and reach a junction with the white-blazed Appalachian Trail (A.T.). Turn right, leaving the A-SB Trail, and follow the white A.T. blazes, which lead under an overhanging rock and into a fascinating rock formation, known as the Lemon Squeezer. The trail climbs through a very narrow cleft in the rocks at the base of the cliff 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 about 100 years ago. This is a good place to stop and take a break.

The A.T. descends from the summit and enters an attractive hemlock grove. After winding through the hemlocks, you’ll reach a junction with the aqua-blazed Long Path, marked by a wooden signpost. Continue ahead on the A.T., which soon parallels a stream, crosses it, then turns right and again climbs over the ridge of Surebridge Mountain.

At the base of the descent, the A.T. crosses Surebridge Brook and turns left onto Surebridge Mine Road. In a few hundred feet, you’ll notice a 100-foot-long water-filled mine pit on the right side of the trail, with a huge pile of tailings on the left side. These are the remains of the Greenwood Mine, opened in 1838 and last worked in 1880. At the north end of the mine pit, you can see a drill mark in the rock face, and several rusted pipes are visible just north of the pit. You’ll want to take a break here to examine these interesting historical features.

Just beyond, where the A.T. turns right, leaving Surebridge Mine Road, you should bear left, continuing ahead on the unmarked mine road. You’ll recross Surebridge Brook but hardly notice it, as the brook goes through the rocks far below the surface of the road! Continue to follow the mine road past a marsh to the right, and look carefully for a huge boulder on the left, with a large tree growing against it. This feature marks the crossing of the aqua-blazed Long Path, which can otherwise be easily missed.

Turn sharply right, leaving Surebridge Mine Road, and follow the Long Path, which once again crosses Surebridge Brook and gently ascends a rise. Continue along the Long Path for another mile, crossing several intermittent streams and boulder fields, until you reach the paved Arden Valley Road, which is closed to vehicular traffic in the winter. The Long Path bears left here, but you should turn right and follow the paved road up to the crest of Fingerboard Mountain and then down to the Tiorati parking area where the hike began.

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

Great hike - A few notes for clarification

I just did this hike (August 2013) and really enjoyed it! There's so much interesting terrain and so many interesting things to see. I'd printed out the description above and brought it with me, and I found a few things confusing, so I've taken the libery of adding some notes to the description which will hopefully be helpful to other people who want to do this hike. I've posted the description with my notes here:

Great Hike

Did this hike on February 26th with some snow on the ground. Judging by the tracks easily visible there was much less people than wildlife out there which is preferable most of the time. The hike description was about as accurate as anyone can be. Well documented.

iron mines loop #3

For an additional mile, you can visit one of the best mines in the park, the Bradley Mine shown on the cover of Ed Lenik's book. Instead of turning on to the Long Path, stay on the Surebridge Mine Road which eventually becomes paved and passes some camp buildings before ending on Arden Valley Road. Bear right. After about  a quarter mile you'll see the remains of an old mine road heading uphill on the left. In case you miss it, you'll soon see lots of tailings uphill on the left. Bushwack uphill to find the mine, a long open slot in front and large cave in back with openings to the sky. It's well worth the effort. When you're done , return to Arden Valley Road and follow it back to the parking area.

Bradley Mine

The description of the Bradley Mine interested me so, this morning I hiked from the Tiorati parking lot to the mine.  There are two trails that lead up to the mine.  Both of them are across the road from the norteast end of the swamp and within a 150 feet of each other.  The left most trail is a much easier hike than the one to the right, which is rather steep and filled with loose tailings.  Both trails have "Restricted Area, Do Not Enter" signs posted near the trails.  The signs do not seem to stop people from visiting the mine as I removed a kitchen trash bag full of plastic bottles, cans, and candy wrappers from the mine. The previous commentor is correct, visiting the mine is "well worth the effort,"  The entrance is a narrow slit in the rock that goes back about 80 feet to the entrance of the mine, which appears to be over a 100 feet deep.  Like all the other mines in the area it is filled with water, but there is a ledge along the right side that goes in about 50 feet.  The mine is at least three times the size of the Boston mine.  I'm glad I made the trip :-)