The trailhead is located between Swamp Road and Stephen Hand’s Path.  If you look North from the parking area you can see where Edward’s Hole Road intersects with Route 114.  Edward’s Hole Road links Swamp Road with Sag Harbor Turnpike, heading north. This road leads across Swamp Road to the trails of Barcelona Neck.  From here you can walk the Paumanok Path in either direction, and you can follow the 6.5-mile Northwest Path to Cedar Point.  The end of our journey into East Hampton’s Northwest, is at the southern end of Three Mile Harbor across the street from the Cathy Lester Preserve on a wide grassy shoulder at the Soak Hides Road, Springy Banks Road intersection.

A warning to the wise; in order to avoid picking up ticks, wear light colored pants tucked into socks, treat clothes with a product containing permethrin.  Do not walk on trails that are not wide or cut back, to allow some distance between your pants and the brush, or high grass.  Trails through beech and white pine forests are safer, because these trees block sunlight and nutrients from the competing plants below.

Recent storms with heavy wind gusts have caused many trees to fall across the trails recently.  Report them to your local trails group, an excellent source for contact information is Hike-LI.org, or if you need help locating those downed trees, ask about the great maps that are available from the hiking groups.

When I am hiking, or writing my articles, I search widely for information, however most of what I know about Long Island’s trails, comes from Mike Bottini’s Trail Guide to the South Fork, Lee McAllister’s book Hiking Long Island, and the wonderful maps created by Larry Paul and Charles Whalen.  Without the hard work of these four people, few of us would be walking the trails.

We start our walk after looking at the trail map kiosk showing the trail we were about to walk.  East Hampton Trails Preservation Society sells a version of this map that you can carry with you.

A short path from the new trailhead intersects a wider path now marked with the yellow triangles of the Northwest Path (NWP) and the white rectangles of the Paumanok Path (PP).  The two trails run north almost 5 miles together, before the PP turns east and then south, and the NWP continues its journey north to Cedar Point.

The convention for turn blazes on the Paumanok Path is modified in East Hampton.  The turn blazes are not two separate vertical rectangles (the top one offset in the direction the trail takes), but rather one vertical rectangle, contiguous with a second horizontal rectangle at its top, extending in the direction of the turn.

We begin our journey walking through a common pitch pine oak mix, with a brush layer of blueberry.  At first, the trail tread is comfortable to walk, however we soon find ourselves traversing a knob and kettle terrain.  The now old ATV damage is still obvious wherever the trail traverses a hill.  A brisk 15-minute walk through the woods will take the hiker across Two Holes of Water Road.  It is easy to see where the trail continues, because there is a deep cut into the berm along the road.  Follow the ridge looking down on Chatfield’s Hole, a peanut shaped kettlehole pond. 

After passing Chatfield’s Hole, to the left, the PP intersects with Foster’s Path, marked with orange (or red) painted rectangular blazes.  It begins by Chatfield’s Hole, immediately north of where the PP crosses Two Holes of Water Road.  It heads northeast while the PP heads in a northwest direction. The north end of this 9-mile loop trail formed where these two great paths meet once again, is at Northwest Road, just south of Alewife Brook Road.  From here we will walk about 7 miles to the intersection of Soak Hides and Springy Banks Road.

The mix of pitch and white pine is changing to mostly white pine as the trail heads north.  After climbing to the top of a small rise, be alert for a huge old lopped tree on the left side of the trail with remains of an old well nearby.  The air is redolent of pine resins.  Pass a large erratic on the left.  Before crossing Bull Path the trail cuts across several driveways.  When I came through here, there was a car parked on the PP obscuring the next blaze to the east.  When you reach Bull Path the trail cuts diagonally across to the right.  Here the shade of the large white pines allows only an occasional mountain laurel to thrive in the brush layer.  A sign indicates that we are now entering Wilson’s Grove. 

The trail leads you across the Northwest Road / Old Northwest Road intersection.  Oak trees are predominating, but white pine are growing in the understory.  The oak trees have been denuded for several years in succession so there is sunlight for the young white pines; they seem to be expanding their territory.  Pass Samp Morter Hollow, a deep kettle with a vernal pond down slope to the right of the trail.

We now travel the dirt roads used centuries ago by the then busy seaport community of Northwest Harbor.  At five corners, an intersection of woods roads, cross over Whalebone Landing Road.  Take the trail that continues north into the Grace Estate Town Park (516 acres).  Soon, on the left side of the trail is Standing Rock, a glacial erratic that sits on the ridge of another kettle hole.  Continue to Scoy Pond, a woods road, where you turn right.  We now leave the Northwest Path, It continues straight northward.  Bayberry, cedar, highbush blueberry abound; you can tell we are near wetlands.  A right turn takes us between Scoy and Little Scoy Ponds.

When approaching the paved Northwest Road on Scoy Pond Road, the woods road is badly rutted by motorized use of this venerable Colonial Road.  After crossing the road note the Old Northwest School House plaque, to the right of the trail, and soon atop a shallow grade, note the Van Scoy cemetery on the left.  After only 200 yards, there is a right turn in the trail, taking you south on Foster’s Path.  The orange Foster’s Path blazes now join the white PP markers. We are on the northern terminus of this 5 mile long trail, heading southeast.  Continuing southeast, Grassy Hollow Preserve still feels like the deep woods of the Northwest.  As the trail continues south the trail corridor narrows.  We are able to walk here because of a well coordinated effort by the East Hampton Planning and Zoning Commission to sub-divide properties allowing for trail corridors.  This enables the hiker to travel off-road to larger green spaces.  East Hampton Trails Preservation Society periodically mows this trail to lessen the tick presence, but at times there is high grass on these wide dirt roads, and precautions against ticks are warranted.  Soon we approach what was once a peach farm, there is cedar attesting to recent disturbance.  There is also bayberry, sassafras, laurel and dogwood.  Once again the trail enters copses of white pine. After cutting across a driveway, note a trail to the right that heads to Northwest Road. Cut across a wide dirt road, and soon you pass Scoys Path to the left.  Once again we enter a narrow trail corridor facilitated though an intelligent sub-division process.  Someday, perhaps large white pines will block the view of pools, tennis courts, and wire fences.

The Foster Trail turns to the right, now you enter the Jump Trail.  There are piles of brush placed across the trail, with walk-arounds.  Cut across Hands Creek Road and continue along Scoy Path.  Here the trail tread is churned up by horses.  Cross over driveways, after a right turn over Van Scoy East, veer to the left into the woods, pass the opening to Montauk Avenue on the right.  Turn left onto a woods road, and pass between several dead end streets.  Another left turn takes you over River Road and then over it once again.  As you enter a wider rolling green space, and walk up a steep slope, be alert for a left turn onto a narrow trail.  After traversing several rolling hills the trail comes out on Springy Banks Road, by our car.