Long Island Trail Lovers Coalition

preserving, protecting and enhancing
our nature and recreation trails




Old Tar Road in Hither Woods



This past Wednesday morning I woke up feeling much recovered from a bout with the flu.  I looked at my website and found that a hike was being led in Hither Woods by Eva Moore of the East Hampton Trails Preservation Society.  It looked like just the thing; I enjoy walking with Eva, it would be a small group on a Wednesday in winter, and the trailhead is easy to find with safe parking.  On this not too cold, clear day a handful of seasoned hikers started out on the Parkway Trail heading east.  I grabbed a map from the kiosk nestled in the woods on the east end of the parking area.  Even though the Parkway Trail has a Serpent’s Back Trail sign, we had to travel several hundred yards before we could make the left turn onto the black-blazed Serpent’s Back Trail.  We passed by the Ocean View Trail (marked with orange blazes) and continued on the Serpent’s Back Trail north.  This trail runs parallel to the Powerline Road.  The Powerline Road is a straight line traveling Hither Hills from north to south.  The Serpent’s Back Trail climbs up and down the undulating knob and kettle topography, much akin to what you might imagine a trip along a serpent’s back might be like.  Where the trail runs straight up the hills, the soil is washing away and ravines are forming; some of these ravines are quite deep.  Ideally a trail is built along ridges and across slopes so that water will wash across them, instead of straight down them.  That is how a sustainable trail is built.  When you look at the Serpent’s Back Trail it seems that it’s built to shadow the path of the Powerline Road;  that may explain the imprudent construction.  On occasion, mountain bikers enjoy the mad rush down the Serpent’s Back, so hikers should be prepared to jump off the trail at a moments notice; bikers usually call out when they see hikers ahead.

We found the blue markers of Flaggy Hole Road and followed that trail to an unmarked trail heading north to the Old Tar Road.  The Old Tar Road runs parallel to and south of the railroad tracks.  Normally if I am walking on my own, I will walk the Paumanok Path to the north of the train tracks or along the Old North Road to the south.  After all, who goes into the woods to walk on a paved road?  Well in all fairness to this path, I found it a pleasant trail to walk, and much of the road seems to have dissolved into the woods.  When we arrived at Fresh Pond Landing Road, we turned right (headed north) to cross the railroad tracks at grade.  Be alert for trains when crossing the tracks; this is an active railway.  As soon as we crossed the tracks we turned right again and walked an unnamed trail east along the railroad tracks until we reached the Paumanok Path.  Traveling west a short distance, we found the short spur trail to the Waterfence Overlook where we spent some contemplative moments gazing out over Block Island Sound.  We then followed the white blazes of the Paumanok Path west for a mile on the portion of the path known as the Stephen Talkhouse Path.  Fresh Pond is visible from the trail and there are several cleared areas where you can rest while looking out over this enormous pond.  We then turned left onto Elisha’s Valley Trail.  This trail took us back over the railroad tracks; we made a quick right on Old North Road, and then a left onto the Petticoat Hill Trail; after a short distance we were back at the parking lot.

The Hither Hills Overlook Parking lot in Montauk is on the north side of Route 27, about one mile east of the Montauk Parkway and Old Montauk Highway split.  It is a large paved lot with several kiosks, one of which usually has a supply of free trails maps.  From the overlook there is a view of Napeague Bay, Harbor, and Isthmus, as well as Gardiner’s Island and the Atlantic Ocean.  This parking area gives access to 3,000 acres of state, county, town, and Nature Conservancy properties and a protected network of 40 miles of trails.  With a free map in hand this a great place to go to create your own personal adventures.  Have fun!

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Long Island Trail Lovers Coalition

Ken Kindler
Open Space & Trails Advocate
Post Office Box 1466
Sayville NY 11782

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