Explore the best rated trails in East 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 69 trails covering 409 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.
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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...
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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,...
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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...
Traveling north-south through Wall Township is the Route 18 Bike Path. The northern terminus is the Municipal Compex, which houses the County Library, the Municipal Court and the Police HQ, as well as...
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 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...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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 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...
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...
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,...
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 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...
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...
Brooklyn's Flatbush Avenue Greenway parallels its namesake roadway for just over a mile from Marine Parkway Bridge to a connection with the Shore Parkway Greenway Trail. The two trails are part of the...
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 Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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...
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 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 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 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 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....
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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...
Brooklyn's Flatbush Avenue Greenway parallels its namesake roadway for just over a mile from Marine Parkway Bridge to a connection with the Shore Parkway Greenway Trail. The two trails are part of the...
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 paved pathway running through West Hudson Park offers a scenic, tree-lined escape between Harrison and Kearny, NJ. The trail provides access to the park’s stocked lake, water park, athletic...
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The idea of a greenway along the Elizabeth River was actually put forward in 1912 by the famous Olmsted Architectural Firm. However, continous flooding made building a trail on the riverbank all but...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
This bike-ped path in Roselle Park, Union County. The bike path is nestled at the bottom of the railroad embankment carrying New Jersey Transit's Raritan Valley Line. Stretching between Galloping Hill...
The Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights of the...
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 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...
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 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 Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....
The Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
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 Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...
The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...
The Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights of the...
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 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 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...
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 Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
Traveling north-south through Wall Township is the Route 18 Bike Path. The northern terminus is the Municipal Compex, which houses the County Library, the Municipal Court and the Police HQ, as well as...
The High Line trail runs 30 feet above the bustling Manhattan streets and sidewalks below, which for trail lovers makes it an attraction in the same league as the Statue of Liberty or the Empire State...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
The idea of a greenway along the Elizabeth River was actually put forward in 1912 by the famous Olmsted Architectural Firm. However, continous flooding made building a trail on the riverbank all but...
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,...
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...
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...
I began in Massapequa with the intention of finishing at Woodbury Road. I made it to Trail View Park at mile marker 8 and turned around. Picture perfect biking weather , but first ride of the season. I’ll definitely finish the trail next outing. The trail is well maintained, filled with walkers, joggers and bikers. I’d definitely recommend for walking and biking
I did this trail a few days ago from Freehold to Highlands and back on my hybrid. I don't recommend a road bike b/c of the countless crossing streets along the way which would necessitate clipping in and out every other minute. The scenery is varied and nice. However the signage is not adequate so you MUST bring phone with maps app. If you're planning to do most or all of this trail, give yourself plenty of time and be patient. It took me almost 5 hours to go 57 miles. Don't plan on setting any Strava pacing records lol...
The Kennedy Catholic School is private property. Do not enter or depart the trail from the southern endpoint at Kennedy Catholic.
The Kennedy Catholic High School parking lot is private property and they have not given anyone walking the trail permission to access the trail via their parking lot . As with any school they are very protective of the student body and control who has access to the school and parking lot. DO NOT PARK IN THE SCHOOL PARKING LOT. Do not access the trail from the Kennedy Catholic High School.
I started This trail in downtown Derby in May 2022. They are doing some construction in the area where they say you can park. Go on a Sunday and park in the City Hall parking lot. Beside the parking and the tons of walker on the path is not bad.
First half of the trail was overcome with traffic noise from the highway running parallel. Most of the path was uncomfortable gravel with very little scenery. 2.5 miles round trip but not inspiring.
Beautiful flat paved trail that continues for 5 miles
Uninteresting trail under power lines that actually does not welcome bikes.
The map here shows the Little Falls section and that does not match the description. Trail head is in Little Falls NJ near the intersection of Reiners Rd & Cedar Grove Rd and ends near the corner of Lynn Pl. and Stewart Ave from there it converts to a painted Bike path on a very busy Browertown Rd. tto a bumpy
We loved this trail! The combination of parks and water views on one side and the vibrancy of New York City on the other made this one of our favorite rides. After biking through city traffic from the brewery where we parked and, of course, later patronized, to the shores of the Hudson River (not for the faint-hearted, but not that scary, really), we began our trek north on the two-lane, almost 13-mile, paved trail.
The Hudson River Greenway starts at the bottom of Manhattan in Battery Park, meandering among the promenades of tall apartment buildings with spectacular views of the river and the steep embankments of New Jersey. The busy Westside Highway separates the trail from the residential towers and commercial warehouses, and when we crossed it, the sound of horns and rumbling trucks seemed to be absorbed by the river.
While the trail is said to be the most heavily used bikeway in America, we pedaled easily around the bikeshare-riding tourists and occasional rollerbladers as we passed Chelsea Pier, the new Little Island, the Intrepid aircraft carrier, and other well-known tourist attractions. There are numerous intersections along the trail, but more are for pedestrian crossings than cars.
Around 100th street, the traffic on the Greenway started to wane as the trail wound under the highway, up some short hills and down below the embankments now rose on the New York side of the Hudson, too. With no view of the city — just the sight of sailboats moored on the wide river — our only reminder that we were still in Manhattan was the far-off expanse of the George Washington Bridge. Eventually, we made it there but had to turn around before the trail’s steep rise, as it continued well past the Bridge to the northern trailhead.
We’ve been walking this trail for years. If you enter at the corner of Cedar and Dobbs, and walk to Paulding, through that gated patch where you pass over the small bridge, which is what we most often do, it’s about 7.5 miles and takes ~2.5 hours at a decent pace. Today we walked from Dows Lane to that gate by the cottage and back around. An hour and fifteen. And if you want a snack or drinks, you can detour down Main St, Irvington. We like to walk to MP Taverna.
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