Long Island Greenbelt Trail
Directions to trailhead
If coming by car, you will need two cars. Take the Long Island Expressway to Exit 42 (Hauppauge) and head east on the Northern State Parkway. Take Exit 45 (Sunken Meadow Parkway) and head north on the Sunken Meadow Parkway for 1.7 miles. Take Exit SM3E (Smithtown) and proceed east on Jericho Turnpike (NY 25) for 4.7 miles to the Long Island Rail Road overpass. Just beyond, turn left onto Redwood Lane to reach the Smithtown station of the Long Island Rail Road. Leave one car here (free parking is available, and no permit is required).
With the second car, head east from the station on NY 25 and turn right onto Maple Avenue. In 1.3 miles, bear right onto Hauppauge Road (NY 111). In 0.8 mile, turn right onto Town Line Road, then immediately turn left onto Wheeler Road (the continuation of NY 111). Continue for 5.4 miles to the Southern State Parkway (along the way, NY 111 becomes Islip Avenue), and take the ramp onto the Southern State Parkway East (towards East Islip). Continue for four miles (along the way, the road becomes the Hecksher State Parkway). Take Exit 44E and proceed east on Sunrise Highway to the next exit (Connetquot Avenue). Turn left at the bottom of the ramp and head south on Connetquot Avenue. Cross the Long Island Rail Road tracks and turn right onto Hawthorne Avenue, which leads to the Great River Long Island Rail Road station (free parking is available, and no permit is required)
Take the Long Island Rail Road from Penn Station in New York to the Great River station on the Montauk Branch. You will return from the Smithtown Station on the Port Jefferson Branch,
This 15-mile hike traverses about half of the 32-mile-long Long Island Greenbelt Trail. Except for one section in the middle of the hike, where the route crosses the Ronkonkoma Moraine, the trail is nearly level. There are a few short roadwalks, and some sections of the trail are adjacent to developed areas, but for the most part, the hike proceeds through pleasant wooded areas. A special feature of this hike is its accessibility by public transportation, as both ends of the hike are situated at stations of the Long Island Rail Road.
From the Great River railroad station, head south on Connetquot Avenue for about 500 feet to Union Boulevard (you can follow an informal path along the west side of the road). Turn left and head east on Union Boulevard until you see a white blaze of the Long Island Greenbelt Trail, which bears left and enters the woods. After passing through a pine grove, the trail reaches Montauk Highway (NY 27A). It turns left, follows the highway overpass over the Long Island Rail Road tracks, then turns left at a sign for the Westbrook Sports Complex. The trail bears right at a “stop” sign and reenters the woods.
A short distance ahead, the trail reaches the dam of Westbrook Pond. It crosses the dam, turns left and follows the east side of the pond, with many openings where you can look across the scenic pond. Particularly interesting are several islands with tall pitch pines.
At the end of the pond, the trail turns left and follows the busy Sunrise Highway (NY 27). It soon turns right and crosses under the highway on a catwalk with a low clearance (you may have to duck), then climbs a flight of stairs and turns left, again paralleling the highway.
The trail turns left at the entrance to Connetquot River State Park Preserve and continues along the entrance road, passing a toll booth and a parking area on the left. For the next 4.5 miles, you’ll traverse this preserve. Just beyond the parking area, the trail turns left again, but you may want to take a short detour to visit an interesting historic building, which is just ahead.
The oldest portion of this building was built as a tavern in 1820. Subsequently, the property was acquired by the South Side Sportsmen’s Club of Long Island, which enlarged the building and used it as their headquarters. The park office, where maps and information are available, is in the most northerly portion of the building and is open Wednesdays through Sundays.
For the next mile, the Greenbelt Trail follows the route of the park’s Yellow Trail (the route is marked with both yellow and white blazes). After turning right and passing a barn, the trail bears left, leaving the paved road, and follows a path in the woods parallel to the road. Interpretive signs along the path provide information on the park and its flora and fauna.
Soon after crossing the road, the trail reaches the park’s Fish Hatchery. Here, the yellow blazes depart to the right, and you should take care to follow the white blazes, which briefly follow a road. Soon the trail bears right and begins to parallel the Connetquot River.
In another mile, you’ll begin to hear the sounds of traffic on Veterans Memorial Highway (NY 454). As it approaches the highway, the trail turns right onto a sandy road and reaches a fence. Hikers go through a gate in the fence, cross the busy highway at a crosswalk, and proceed through a gate on the other side, where the trail continues on a wide woods road. In a short distance, the trail crosses an abandoned paved road and continues on a footpath.
In another third of a mile, the trail turns left and crosses a boardwalk over a wet area. It then bears left at a fork and immediately turns right onto a woods road, with houses visible on the right. The trail now crosses under the Ronkonkoma Branch of the Long Island Rail Road, leaving Connetquot River State Park Preserve and entering Lakeland County Park.
Just ahead, you’ll reach Honeysuckle Pond, which feeds the Connetquot River. The trail turns right to skirt the pond, turns left onto a long boardwalk, then turns left onto a dirt road, with views over the pond. Before reaching a basketball court, the trail turns right onto a paved path, passing a parking lot for the park on the left.
The trail now leaves the park and turns right onto Johnson Avenue. It follows the street for only 200 feet, then turns left at a sign for the Greenbelt Trail and reenters the woods, proceeding through a pine grove. Soon, the trail bears left at a chain-link fence and follows along the fence for about a quarter mile (portions of the fence are missing).
Upon reaching the service road for the Long Island Expressway, the trail turns right and follows along the service road to the underpass at Terry Road. You’re now at the halfway point of the hike. The trail turns left, goes under the expressway, and continues ahead on Terry Road until it reaches a power line right-of-way. Here, the trail turns left and follows under the power lines for about 500 feet, then turns right, into the woods. It bears right at the next two forks and passes a horse farm on the left.
In about half a mile, the trail crosses Old Nichols Road. A 7-11 convenience store is located a short distance to the right, and you might want to stop at the store for refreshments. The trail reenters the woods, passing the back yards of homes on the left.
Soon, the trail turns right and climbs a small hill. The ascent is relatively minimal, but this is the first time on the hike that you’ve encountered a climb of a natural feature. You’re now crossing the Ronkonkoma Moraine, a glacial moraine that runs the length of Long Island. At the top of the hill, the trail bears left and begins to descend.
Next, the trail climbs another hill. With houses visible ahead at the top of the hill, the trail bears left and descends to power lines. It turns right and follows the power lines, climbing a little, then bears right at a fork in the power lines and reaches the Long Island Motor Parkway.
The trail crosses the road and reenters the woods at a gate. You’ll notice that a separate route is provided for mountain bikes here. The trail now climbs once more and reaches three viewpoints, marked by benches. The view from the first bench has largely grown in, but there are limited views to the north and northeast from the next two benches.
The trail now descends rather steeply. With a recreational complex and pool visible on the right, the trail bears left, and it soon begins to run along a chain-link fence – the boundary of a golf course on the left. The Greenbelt Trail briefly joins a woods road and runs concurrently with a blue dot-on-yellow-blazed trail.
After turning right, away from the golf course, the Greenbelt Trail enters the Hidden Pond Park of the Town of Islip. It bears left at a picnic area and passes Hidden Pond, which is dry for much of the year. Take care to follow the white blazes through this area, as the trail makes a number of turns and intersects several trails with other blazes.
At the end of the park, the trail turns right and follows a narrow corridor between chain link fences, with the golf course on the left and backyards of homes on the right. It soon reaches Town Line Road, where it turns left and follows along the road for a short distance, then turns right and crosses the road.
The trail parallels a drainage ditch, then passes by a wetland and reaches McKinley Pond, marked by a small dock on the left. Continuing along, the trail crosses a number of seasonally wet areas on short boardwalks, many of which were built as an Eagle Scout project. After going across a grassy field, it crosses the Nissequogue River on a metal-grate footbridge and turns right. The trail then goes over a long stretch of boardwalk and several shorter boardwalks, and it passes by condominiums on the left.
The trail soon reaches the busy Nesconset Highway (NY 347). Although a crosswalk is provided, the traffic on this highway is very heavy, and extreme care must be exercised when crossing the road. At this writing, there is a construction project underway on the opposite side of the road. Hikers should turn right and follow the road until they see a sign for the Greenbelt Trail at the end of the construction area. The trail turns left, skirts the construction area, then heads into the woods.
Soon, the trail comes out at the intersection of South Avenue and West Avenue. It turns left and follows West Avenue to a dead-end, then continues ahead into the woods. For the next mile or so, the trail traverses pleasant woods. After a while, it crosses a bridge over a stream and parallels the back yards of homes. A short distance beyond, it passes behind a shopping center and reaches an intersection with a sandy road at a graffiti-scarred kiosk.
The trail turns left onto the road, crosses a footbridge over the Nissequoque River, then continues along an abandoned paved road which curves to the left and begins to parallel Hauppauge Road (NY 111). The trail turns right onto Wood Hollow Road, crosses Hauppauge Road at the intersection, then turns left and parallels the road. It soon re-enters the woods, following a corridor between homes on the right and the highway on the left. In a short distance, the trail curves to the right. After passing the scenic Miller Pond on the right, the Greenbelt Trail reaches a parking area for the pond along Maple Avenue. Here, it turns right, crosses the dam of the pond, then bears left and again reaches Maple Avenue.
Turn right and head north on Maple Avenue. The Greenbelt Trail turns left onto Wildwood Lane, but to reach the Smithtown railroad station, you should proceed ahead on Maple Avenue for half a mile to West Main Street (NY 25). Turn left onto West Main Street, then turn right onto Redwood Lane, which leads to the Smithtown Long Island Rail Road station on the Port Jefferson branch.