Explore the best rated trails in North Massapequa, NY. Whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail. With more than 65 trails covering 395 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the...
At 2.6 miles, the Staten Island Greenbelt Multi-Purpose Trail offers a nice jaunt for joggers, walkers, and cyclists alike. The crushed-stone path is 6-feet wide and runs from Rockland Avenue to...
The Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...
The Laurelton Greenway is a short but well-maintained multiuse path connecting the neighborhoods of Jamaica and Rosedale in southern Queens, NY. The two-lane paved trail starts in Jamaica, and travels...
The West Essex Trail follows a short distance (just under 3 miles) of the former rail bed of the Caldwell Branch on the old Erie-Lackawanna Railroad. The trail runs between the EssexPassiac county...
It’s hard to believe that a noisy locomotive once ran through here, given that stillness is a defining characteristic of the Middlesex Greenway. Even when people pour onto the trail from the adjacent...
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
The nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
Like Wantagh State Parkway, Ocean Parkway was built in the postwar 1930s to provide access to the crown jewel of the state park system, Jones Beach State Park. Unlike the former road, however, this...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
The Ocean Parkway Trail closely follows its eponymous thoroughfare nearly 5 miles through several Brooklyn neighborhoods, ending only a block from the popular Coney Island boardwalk. Those traveling...
The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...
The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
_160375_sc.jpg)
The Patriots' Path covers roughly 35 miles of terrain and is open to mountain biking, horseback riding, cross-country skiing and hiking. The multi-use trails links parks, open space, recreational...
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
The two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
The Fort Washington Park Greenway brings residents and visitors to Washington Heights right up to the edge of the Hudson. The mile-long trail begins near the pier at the end of Dyckman Street and...
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
The Perth Amboy Harbor Walk offers scenic views of the Raritan Bay and Raritan River as it hugs the shoreline of the City of Perth Amboy, founded in 1683 and home to one of the nation's oldest ports....
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
The Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
The New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
The New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
New York City's East River Greenway offers views of the East River, Queens, Brooklyn, and the iconic bridges that connect these boroughs to Manhattan. The paved pathway traces the waterfront on one...
The Sandy Hook Multi-Use Pathway travels 8.7 miles alongside the picturesque beaches and historical monuments of the Sandy Hook peninsula. The pathway begins in the Gateway National Recreation Area...
The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
The Perth Amboy Harbor Walk offers scenic views of the Raritan Bay and Raritan River as it hugs the shoreline of the City of Perth Amboy, founded in 1683 and home to one of the nation's oldest ports....
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
The Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
Fun park for walks. Has fountain and ducks and paved trails for walking biking or running
Plenty of curves and turns not to mention hills. Visiting from Florida and fairly new to cycling so the hills were a good challenge! Most of the street crossings have detectors that automatically stop traffic. Good signage for approaching hills. Pavement in excellent condition.
Perfect walk for our standard poodle. Just the right length. Friendly people . A few hills
Beautiful in fall, but a workout going from Brewster. A few major hills.
Been on this trail many times! Will return!
Some sections are worse than others with tree roots under the pavement, signs are not located thru Matawan, (train station, etc.) need clean bathrooms along the route.
Recommend!
Beautiful scenery. (some points you can see NY!)
Only acceptable for the large wheels bikes. Can not enjoy rollerblading or a ride on a smaller bikes.
This is a great, scenic route that weaves its way through at least 3 different parks in the area, and under quite a few bridges. Mainly flat and most of the trail is covered by nice tree canopy to keep you shaded. We had a great time traveling the entire length of the trail (and back) today. However, that said, I do have to agree with some of the other posts on this site...the path can get a bit congested in areas (like the trail head by the duck pond, and as you ride through the parks). This is the only reason i didnt give a 5 star review. A lot of the walkers didnt honor the keep right except to pass rule, others walked 2 sometimes 3 abreast taking up the majority of the pathway, and still others stopped in groups in the middle of the trail. My advice would be to hit this on off peak days/hours, but if you do go on a weekend or holiday, and your on a bike, just make sure you announce yourself and advise those in front of you that you are passing on the left. The majority of trail users were considerate and moved over to the right when needed. All in all, it was a great ride, and i would recommend it to beginner to intermediate cyclists.
i love walking here with my dogs. i see turtles, snakes, butterflies, hummingbirds, (lots of other birds) and countless native plants.
It’s mostly flat and has lots of great scenery, especially towards the south of the tail. I biked with my friend for 7 miles before we realized it would take another 7 to get back to the car. We loved it anyway! Great workout without feeling you worked out!
This trail is just 1.2 miles from our home and is by far our favorite trail to ride. We enter the trail at the northern endpoint in Dutchtown in Haverstraw and ride to Nyack Beach Park and back. The 12.3 mile ride can be done in less then an hour or you can ride up the mountain and include the loop around Rockland Lake State Park where you can also park and enter the trail from. This trail winds up and down along Hook Mountain State Park with views from high over the Hudson River and then down along the rivers edge to Nyack Beach State Park. If you can get out during the week you can have the trail to yourself. Hybrid or mountain bikes are the better choice but you can make the trip on a road bike if your carful. If you live in this area you shouldn't miss this hidden gem.
We have biked this trail numerous times over the past 7 years and it's one of the trails we always go back to. We usually start at the Millwood parking lot and head north. The bridge over the Croton Reservoir is the highlight of the trip. There are horse farms and wooded sections along a rock gorge before you merge onto the Putnam Trailway. The trail is crowded on weekends so if you can get away during the week you will have this trail to yourself pretty much until the afternoon.
Get Your 2018 RTC TrailNation Jersey!
Download the TrailLink mobile app and take TrailLink with you!
Donate and Get a FREE 2019 RTC Guidebook!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_160375_st.jpg)
