The numerous trails running through Harriman State Park make this loop tricky to follow, but the multiple attractions along the trail make it worth hiking. From the Elk Pen parking area, follow the white-blazed Appalachian Trail over a hill to a gravel road bordering Island Pond. Turn left onto the gravel road, but keep an eye out for the white trail to branch off to the right, and follow this to Lemon Squeezer.
An inconvenience for thru-hikers making their way along the over 2,000 mile long Appalachian Trail, Lemon Squeezer is a highlight for day hikers on less strenuous trips. Blazes painted on one of the two boulders at the entrance to the cool rock formation lead the way to the squeezer itself: a 1-foot-wide path through massive rocks at a jaunty 15 degree angle. Climb to the top of Lemon Squeezer via the easy way or the hard way, and once you are finished exploring, head back out the entrance and turn left onto the Arden-Surebridge Trail, blazed with a red triangle on a white background.
Follow this fern-lined trail until the junction with the Lichen Trail, marked with a cairn at the fork in the path. The Lichen Trail blazes are a blue “L” on a white background. Blazes are painted on the rock face as the trail ascends, and cairns lead to a wide vista. Soak in the views of Harriman State Park and Island Pond, which the trail passes later, before continuing along the Lichen Trail.
Shortly after this viewpoint, the Lichen Trail intersects with the Ramapo-Dunderberg Trail, blazed with a red dot inside a white circle. Turn right onto this trail and follow it until the yellow-blazed Dunning Trail intersects at a cairn. Turn right at this junction and follow the yellow blazes to the abandoned Boston Mine, last used in 1880. Use caution exploring the open-top mine.
Follow the yellow trail until it joins an old woods road, then turn right onto the road. Follow the road until the Arden-Surebridge Trail (red triangle on white background blaze) joins it and continues to the left. Follow this trail along the western edge of Island Pond to the junction with the white-blazed Appalachian Trail. Turn left here and retrace the beginning of the hike back to Elk Pen parking.
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