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.
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 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 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 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 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 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 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 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...
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...
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 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 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 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...
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...
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 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...
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 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 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 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...
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 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 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 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 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 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...
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 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...
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...
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...
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...
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...
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 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...
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 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 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...
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...
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...
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 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 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...
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...
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...
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...
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...
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 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 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...
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...
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 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 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 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 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 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 trail itself is a beautiful 3.5 mile paved road traveling through Metuchen, Edison and Woodbridge. Great for walkers, joggers and bicyclists. However, as another person mentioned, people do not stay to the right of the road. People walking in a group will continue walking at you without adhering to the rules of social distancing and moving over to their side. It's a shame because it is a lovely walk however people need to be more respectful with regards to social distancing.
I've ridden this trail three times now on a loaded touring bike (rear panniers). Some of the rolling hills at the Nyack end definitely require some mettle and/or caution, but I never felt at risk of losing control. I think the "moderate" experience level is justified.
For reference, my bike was outfitted with 35mm tires. The first time was with moderately knobby tires (Schwalbe Mondials) which I decided were overkill for a mostly paved tour; the second time was with slicks and I felt no less confident. The weight of a touring load probably helps with traction regardless of the tire. Experience with changing your gears quickly and often is very helpful here. I was with friends who were on single speeds and they had to walk quite a bit of it :)
We took our bikes today June 23rd 2020, and someplace in Mahopac the town closed partially the trail, we couldn’t find the way around, wish they put signs for a Detour. Other than that, trail is beautiful
Fun little trail that connects Edgar Felix Trail to Wall Township. I noticed it said “Inline skating” as an appropriate activity for this trail. I would not recommend this. Portions of the trail are extremely steep and the trail itself has many bumps from tree roots growing beneath. Probably time to repave this trail soon.
The upper part gets too narrow to enjoy. Too many people. The lower part starting around South Street Seaport and up is much more spacious and enjoyable
Plenty of room, not too crowded. Waterfront views of boats and bridges on the side
Really spacious trail way all around the island. Really nice views all around and not crowded
Really nice views. Could get confusing so use TrailLink maps to get around. It has sewer smell at parts of the island. Lot’s of people BBQing all around.
I utilized the trail to access the just opened shared-use path over the Mario Cuomo Tappan Zee Bridge. A spectacular ride but caution is warranted. The new path has walkers and joggers separated from cyclists by a painted line. With users travelling in both directions it can get pretty tight.
Also note that unlike the Rockland side with direct access to the Esposito and Old Erie Path trails the Westchester side ends at busy Route 9/ Broadway. It is a fairly short on-street ride to the Croton Aqueduct Trail (not suitable for road bikes) and a longer street ride to the North Country Trailway.
The Bike path description and the previous review pretty much say it all. I would add that after you exit the trail on the north it would be very worthwhile to ride on park roads to the highest point in the park at the Sawmill Picnic Area where there are great views of Piermont, the Piermont Marsh, and the Hudson River.
Traillink is a free service provided by Rails-to-Trails conservancy
(a non-profit) and we need your support!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_160375_st.jpg)
