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 63 trails covering 392 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 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 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 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 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 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...
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 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...
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...
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 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 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 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...
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,...
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 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 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 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 Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
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 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...
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 Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
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...
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 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...
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 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 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...
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...
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 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 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 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...
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 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 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 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...
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...
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...
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...
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...
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 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 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...
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...
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...
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 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...
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 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...
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 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 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 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 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 Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
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...
The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...
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...
18.35 mile round trip for me from the Cedar Creek Park on the Jones Beach Bikeway connecting to the Ocean Parkway Coastal Greenway at the Jones Beach theater. Beautiful ride, the food stands come in handy too!
Took my 9 year old for his (and my) first ride on this path today. Easy and relaxing bike ride. Wasn't sure he would be into doing the whole 7 mile round trip on his first time out, but it turns out we were having so much fun we just kept on rolling! Excellent ride for beginners, and still fun for more experienced riders. I love that it is mostly all shaded too! We will definitely be back sometime soon!
I road this trail for the first time this past week. It's nice but way too short! I did take a detour into Piermont which extended it nicely and stopped at the bike friendly Bunbury's.
As of July 2019 the paved surfaces ranged from fair to excellent but were mostly good. Intersecting loops and dead ends provide approximately 12 miles of trails but these were non-continuous secondary to construction blockages. This trailway is scheduled to be completed in the spring of 2020. The trails pass mostly baseball fields, soccer fields, picnic areas and municipal storage lots which give parts of the park an industrial feel. There are several good quality bathrooms attached to snack bars along the trail. The views of east Manhattan and the standing waves in the Hell's gate section of the East River are excellent. On the island you may also pass Icahn Stadium, The New York Police Department Harbor Unit, John McEnroe Tennis Academy, a native plant garden and the Manhattan Psychiatric Center Hospital (formerly known as Blackwell's Island Lunatic Asylum).
Parked at the trail head in Millwood & rode North. Did total 35 miles. 17 1/2 one way.Rode into the Putnam railway,as they run into each other.The trail is very scenic.You ride pass some towns. But is hilly & can be challenging ..for some..There are sections that are bumpy.. (tree roots) a lot are marked..just have to pay attention..There are some road crossing..all & all we had a good ride..but don't think this trail is for everyone,not just an easy flat trail.. We had lunch at the Tazza cafe on Rt 133,near where we parked,it was great. Toward the healthy side,loved it..
Before we began we talked to some people at the trail head, and decided to use it to explore the town of Piermont NY which has a nice little downtown and a beautiful pier. About 1/4 mile into the trail there is a dirt path going to the right...went on that until we found a tiny hut labeled 'Piermont' (it is a small museum). Getting advice from a jogger, we went down the steep hills there into town..had coffee at a neat little shop then and eventually found the pier. We had to walk up the steep hills on our return. This was an unexpected adventure, Next time we will do the entire trail.
As of June 2019 the paved surfaces ranged from excellent to fair but were mostly good. Branching and intersecting bicycle trails make it very easy to get lost so having a detailed map of the route is essential. Parking at the recommended lot at Orchard Beach costs $8 on weekdays and $10 on weekends so you may want to try street parking near one of the entrance points.
We rode this trail on 6/16/19 North from the Tait Road parking lot to its end in Newtown and back, approximately 20 miles total. Almost constantly shaded by trees, very removed from highway traffic, felt like I was in the deep woods at many points. Initial section runs along a ridge and you can look down and see the rivers. Some parts are cinder, some paved, some dirt; there were one or two short sections of gravel; you need a hybrid or a mountain bike (no skinny road bike tires). But overall a very nice ride and worth your time! The section near Tait Road had a number of walkers and families with kids; as we got further north it was much less crowded. As noted, there are several points where you have to cross a road or ride on-road for a short section to get to the next part of the trail, so if you're riding with kids please be aware of this. But we found those sections fairly easy to navigate, even though the signage isn't as good as it could be. There are a few small uphills but they're very short ... just about all flat. Nice to have something like this close to our home in Fairfield County!
My wife and I have been riding the North County Trailway off and on for about 10 years now. Always enjoyable; passes through several small towns but often through unpopulated areas. Trail continues to the south (South County Trailway) and to the north (Putnam County Trailway), so it's possible to start at the NYC border and bike for 40+ miles on well maintained trails.
Great biking path for those who want moderate exercise and to enjoy nature. There are no Traffic lights or cars to navigate around so it’s great for families with kids. The path is well maintained and wide enough in most spots to easily navigate around walkers. You may have to slow down to pass people so if you are a cyclist looking for a more intense workout or speed you may want to stick to the off hours like early morning or late during the week
This bike path is paved and has good ocean views. And a LOT of walkers. There is a designated bike lane, no one seemed to care but did reluctantly allow room when announced. There was a DJ by the pier, an ice cream truck and portapotty. Parking at Bradley Point Park was by meter machine at $1.5p/hr. Too heavily populated to return. My husband had a bike trailer with our boys. I was the lead announcing our coming
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