Explore the best rated trails in Stony Brook, 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 66 trails covering 428 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.
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 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 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 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 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 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 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...
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...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
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 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 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 North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10-mile multi-use recreational path and runs along the former Wading River railway corridor in Brookhaven—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...
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...
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 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 Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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 Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
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 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 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...
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 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...
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 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 Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
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 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...
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,...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10-mile multi-use recreational path and runs along the former Wading River railway corridor in Brookhaven—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,...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on 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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 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...
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...
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...
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...
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 Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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 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...
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 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...
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 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 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 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 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 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...
July 2021, midweek afternoon
After a 2 hour drive from my home in New Paltz, NY, there is a cheapish pay parking lot with a beach right on the Long Island Sound. Maximum time allowed was 4 hours, plenty to ride eastward on part trail, mostly city streets, over to the light house park, making it a much longer ride, 26 roundtrip miles I think. When I got back, hot and sweaty, I changed my bike clothes in the parking lot outhouse and soaked in the nice ocean water. I went back a second time 6 weeks later just to ride westward along urban streets for an hour. Again, in late August I really enjoyed soaking in warmish ocean water with only 2 other people visible.
(This is our secret biking place...don't share!)
This trail is a good idea in terms of riding from Van Cartland Park to City Island. The execution however leaves a lot of room for improvement. The mostly asphalt paths are in rough shape -cracked, tree trunk and root damage, in need of lane markings both to designate the trail and to help keep people in the proper lanes (a big issue considering the number of walkers using this trail). There are signs to help navigate this trail but they are busy and difficult to read for bikers and could be more prominent as it’s easy to miss turns at intersections.
I ride a lot of rails trails and this frankly did not blow me away. There are some great sections with great canopy and nature but there's miles that feels like a glorified sidewalk next to traffic. A couple very large cracks and sections with bad pavement in the New Haven area. You'd think that would be the most maintained section but I guess not.
The Maybrook has quickly become one of our favorite rail trails. Basically brand new, uncrowded, lots of interesting sights along the way including multiple water views and lots of greenery.
Today we rode from the Brewster trailhead at Lake Tonetta both ways: Out and back to the CT line, and then out and back in the other direction up past the Ice Pond, for a total of about 20 miles. The first segment to the CT line was new to us; there is an on-road detour due to a bridge out at Peaceable Hill Road. You walk down a flight of steps, ride down Peaceable Hill Road to Rt. 6, turn left on Rt. 6, go down the hill, turn left again on Rt 6 and then ride up the hill past the Honda dealership where another set of stairs on the left will bring you back to the trail. These stairs are fairly steep but it can be done. The road has a shoulder but is a bit busy; experienced road riders will find this easy to navigate, others can simple walk along the sidewalk. Your reward is that the other end of the trail as you ride east is a very nice section past East Branch Reservoir, including a long section right along the water. One way mileage is about 5 miles, as the trail ends at the Connecticut line. The second section we rode, going North from the Brewster trailhead at Lake Tonetta, offers views of the “ice pond” and the “great swamp,” with hills in the distance. Today’s one way mileage for that section was also about 5 miles; a great ride, and you can ride much farther (we often go as far as Whalley Lake, just not today) as the trail goes all the way to Hopewell Junction where you can pick up the Dutchess Rail Trail. Check the Empire State Trail website for more info.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
I prefer to travel out to Jones in the Fall and Winter months but this trail is great all year round. The board walk gets very crowded on the weekends and throughout the summer, however, the trail continues PAST the board walk (this trail map should be updated!) the concrete trail extends to the west end, there are paths that allow you to check out the fishing spots which require parking permits so being able to get there by bike for free is a plus. Just be aware that after memorial day you must pay $$$ for parking at Jones Beach, which is why I recommend this trail for the off season.
What a lovely trail! We had a great time with our 2 year old daughter on the back of the bike… shaded, not too hilly and playgrounds for her along the way.
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
The Kennedy Catholic School is private property. Do not enter or depart the trail from the southern endpoint at Kennedy Catholic.
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