This hike incorporates several key features including Island Pond, the Lemon Squeezer and Island Pond Mountain. The hike starts from the Elk Pen Parking lot off of Arden Valley road.  While Arden Valley road is closed in winter, the section to reach the Elk Pen remains open year round.  Follow the Appalachian Trail (AT on maps, white markers on trail) from the parking lot across an open field.  Once out of the field and into the forest, the trail begin a steep uphill climb for about .75 miles until leveling off and then descending onto to Island Pond rd (unmarked forest road).  The AT turns left onto Island Pond road then leaves the road, crossing a stream and ascending the most scenic part of the hike.  This area has open forest views and great views of the pond.  Passing the pond and continue on the AT until the junction with the Arden-Surebridge Trail (red markers).

Descend this section to the large rock outcropping.  This is the Lemon Squeezer, a geological formation of rock that creates a narrow passage. The difficult section is easily passed on the left.  After the Lemon Squeezer it is a moderate ascent through open forest to the top of Arden Pond Mountain.  After .75 miles from the Lemon Squeezer, the AT meets the Long Path (turquoise markers).  Turn right onto the Long Path and follow .6 miles through Dismal Swamp.  At that point the Long Path meets back up with Arden-Surbridge Trail.  Turn right on the A-S Trail (red markers).  After .25 miles you are back at the start of the Lemon Squeezer.  Ascend the hill and turn left continuing on the A-S Trail.

Stay on the Arden-Surebridge Trail for 3.2 miles.  The section of the Arden-Surebridge Trail gets very little traffic and is not well maintain.  It is not uncommon to climb over down trees. The trail ends back on the AT just at the point where you originally left the open field.  Turn left and follow a short distance back to the parking area.