Explore the best rated trails in 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 71 trails covering 436 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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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 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 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 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....
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 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...
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,...
Prepare to be whisked into the past when you take the Edgar Felix Memorial Bikeway. The paved trail follows a short-line railroad corridor from the coastal city of Manasquan to a village at Allaire...
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...
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...
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 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...
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...
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...
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...
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...
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 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...
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...
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...
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 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 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 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 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 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 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...
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...
The tree-lined 22.5-mile Henry Hudson Trail is the definition of scenic variety. Traversing both urban and natural environments, the route passes wetlands, streams, fields, and the Garden State...
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...
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 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...
Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...
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....
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
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...
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...
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...
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along 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...
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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...
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...
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
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...
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 Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...
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...
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...
Prepare to be whisked into the past when you take the Edgar Felix Memorial Bikeway. The paved trail follows a short-line railroad corridor from the coastal city of Manasquan to a village at Allaire...
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 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...
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...
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 Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
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...
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...
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 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 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...
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...
I never have been in this place before Is so nice, clean and secure. I would walk again definitely.
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
Recently rode this from Freehold to Highlands on my hybrid bike. I would not recommend a road bike because of the countless # of crossing streets which would require clipping in and out every other minute. Overall the scenery is nice. However the signage is poor in some parts where the trail is disconnected. You MUST bring a phone w/maps app in order to not get lost. Also if you plan on riding all or most of the trail give yourself lots of time. It took me nearly 5 hours to ride 57 miles so no Strava 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.
Great trail with beautiful views. In some section you're secluded (so be mindful) if alone. Trail is clean and flat best trail so far of 2022.
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.
I rode most of the Maybrook Trailway on a cold Easter Sunday in 2022. We started in Hopewell Junction and ended at a park right outside of Brewster. The trail is completely paved, very wide and in immaculate condition. There are mile markers but they are easy to miss and I wasn't quite sure what they were counting up or down towards as they did not start at 0. There are slight elevation changes that made riding back feel a little more difficult but there are no significant hills.
The scenery is nice but it is very monotonous with lakes being the only real variation to the trees and the disused railroad that encompasses the rest of the Maybrook Trailway. Since I did not make it all the way to Brewster proper I cannot speak to any sort of facilities there but the only real bathrooms or shelter/benches I found were at the very beginning in Hopewell Junction and where we ended near Brewster.
Beautiful flat paved trail that continues for 5 miles
Uninteresting trail under power lines that actually does not welcome bikes.
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