Hike Description:

When thinking about hiking on Long Island, most people envision flat, relatively monotonous terrain. Indeed, most hiking trails on Long Island are flat, or nearly so. But this hike is a notable exception. It is situated on the Harbor Hill glacial moraine, which features undulating terrain and some steep climbs and descents. In fact, this may be the most challenging hike (from the point of view of terrain) on Long Island.

From the parking area for Trail View State Park on Jericho Turnpike, head into the woods and proceed north, following the white blazes of the Nassau-Suffolk Greenbelt Trail. (You will be following the white blazes for the entire hike.) The trail follows undulating terrain, passing many large trees. In three-quarters of a mile, the trail begins a steady descent on switchbacks, soon reaching Woodbury Road. It turns left and follows the road for a short distance to an intersection with a traffic light.

The trail crosses Woodbury-Syosset Road at a crosswalk, bears left and reenters the woods. Again, it follows undulating terrain until it climbs a rise, with the ruins of an old car on the left at the top, and levels off. A short distance ahead, the Nassau-Suffolk Greenbelt Trail crosses an unmarked trail and descends wooden steps towards the Port Jefferson Branch of the Long Island Rail Road.

At the base of the steps, the trail turns right onto a level path. Just ahead, follow the white blazes, which turn left and descend another flight of wooden steps. The level path, now blazed blue, continues ahead. The blue blazes indicate a route for bicycles, while the white-blazed trail is for hikers only. The use of bicycles on steep trails in this area resulted in much erosion, and the wooden steps here (and others just ahead along the trail) have been constructed by the Long Island Greenbelt Trail Conference to provide a more attractive route for hikers.

After descending the second set of wooden steps, the white-blazed trail turns right on a dirt road, with the railroad tracks immediately to the left. Just ahead, the blue-blazed bike trail joins from the right, and both trails turn left onto the private Whitney Lane and go through an underpass beneath the Long Island Rail Road tracks.

The trails now turn left and passes through a bamboo thicket. A short distance beyond, the white and blue blazes turn right. Just ahead, follow the white-blazed trail as it turns right, leaving the blue-blazed bike trail, and climbs on wooden steps. At the top of the steps, you go through a wooden stile, placed here to prevent bicycles from using the hiker-only trail.

The trail now turns right onto a level path, but just ahead, it bears left at a fork and crosses another bike trail (marked with white triangles). In another quarter mile, the white-blazed Nassau-Suffolk Greenbelt Trail bears right onto a wider path, and just ahead, it bears right at a fork, joining a yellow-blazed trail (at this writing, there are only yellow blazes at this fork). For the next 1.2 miles, you will be following both white and yellow blazes.

You are now entering the Stillwell Woods Preserve, a 270-acre Nassau County park. The white/yellow trail runs along the right side of an open meadow, with many wildflowers – a welcome contrast to the woodlands you have traversed along the route of the hike up to now.

Bear right at the next fork (again, there are only yellow blazes at the fork), leaving the meadow, and then right again at the following fork, just beyond. In another quarter mile, the trail joins a wider path coming in from the left, then immediately turns sharply left. Again, the trail begins to traverse undulating terrain. After crossing a blue-blazed bike trail, the white/yellow trail turns right and soon passes a bench – a good spot to take a break.

About a mile from the meadow, the yellow trail turns right, leaving the white-blazed trail. You should continue ahead, following the white blazes. In a short distance, the trail crosses paved Stillwell Lane and turns right onto an abandoned railroad grade. This railroad grade was the route of the Hicksville & Cold Spring Branch Railroad, chartered in 1851 to construct a rail line from Hicksville to Cold Spring (as the village of Cold Spring Harbor was then known). This portion of the line, extending from Syosset towards Cold Spring, was graded in 1862, but due to a dispute between residents of that community and the management of the Long Island Rail Road, rails were never laid on the roadbed. Instead, a new line (the route of today’s Port Jefferson Branch) was constructed on a more southerly alignment. Over 150 years later, this railroad grade, still in remarkably good condition, has become a hiking trail.

After following the railroad grade for about a third of a mile, the trail turns right, leaving the grade. It crosses a footbridge over a stream and turns left to parallel Route 108. In 0.2 mile, it crosses Route 108 at a crosswalk with flashers, entering Suffolk County.

For the next 1.2 miles, the Nassau-Suffolk Greenbelt Trail heads north on a winding, undulating route, roughly parallel to Route 108. The sounds of traffic on this busy road can be heard, but the road itself is not visible for much of the way, especially when there are leaves on the trees. The ups and downs on this section are more pronounced than on the sections you have traversed so far. Portions of the route follow an old road, with gentle grades, but other portions are routed along steeper footpaths, with some wooden steps. You will encounter several stands of rhododendron, a species that is native to Long Island but not often found along its hiking trails.

After paralleling a chain-link fence on the left, the trail descends wooden steps, crosses paved Lawrence Hill Road, and enters Cold Spring Harbor State Park. The 1.1-mile route of the Nassau-Suffolk Greenbelt Trail that traverses this park has been described as “one of the most strenuous sections of trail on Long Island.” The ups and downs on this section are steeper than on the previous sections, and this section is popular with local residents who are looking for a good workout. Numbered markers are posted on trees along this trail section, and the numbers correspond to those shown on the park map available online, thus permitting you to determine your exact location.

Towards the end of the section, you’ll notice the picturesque building of the Cold Spring Harbor Library below on the left. A short distance beyond, you’ll reach a panoramic viewpoint over the waters of Cold Spring Harbor. When there are leaves on the trees, you can take in the view by climbing a little to an open area on the right of the trail. The trail now begins a steady descent, and it ends at a kiosk at the southern end of the parking area on Harbor Road for Cold Spring Harbor State Park.