Explore the best rated trails in Greenwich, CT. Whether you're looking for an easy walking trail or a bike trail like the West Hudson Park Path and West Essex Trail. With more than 82 trails covering 534 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 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 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...
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...
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Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
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 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 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 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,...
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...
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
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 Randolph Trail system covers 16 miles of pathways through five parks, the Clyde Potts Reservoir watershed and 2,000 acres of pristine open space. The trails link schools and neighborhoods and also...
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....
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...
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 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...
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 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
The William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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 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...
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...
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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...
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...
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 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...
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 Randolph Trail system covers 16 miles of pathways through five parks, the Clyde Potts Reservoir watershed and 2,000 acres of pristine open space. The trails link schools and neighborhoods and also...
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 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...
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 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...
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 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 first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
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...
This 2.1-mile long paved path runs directly adjacent to (about 30-40 feet off of) the Boulevard in Mountain Lakes, NJ, and follows the exact route of a former trolley line operated by the Morris...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
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 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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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 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 nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
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 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 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 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...
This trail is located in the Mahlon Dickerson Reservation which is a unit of the Morris County Park Commission. The trail follows an abandoned railroad bed through hardwood forests, past ponds, swamps...
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...
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,...
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...
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,...
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...
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 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...
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 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...
My family and I took a lovely bike ride on this trail today. However, it’s important to share that (at least) one of the two parking lots (the southern-most one) is meant for New Milford residents only, and the cops will get your car towed if you’re not from New Milford. A true shame to exclude neighbors from enjoying the trail like that.
An absolute joy for all bikes. Smooth well maintained trail which runs through a couple towns (not in the street) for easy access to grub.
Has anyone been out on the trail since the storm?
thinking of riding it tomorrow and wondering if any down trees blocking it
August 2020
Not my kind of trail. It is here, I did it, but did not enjoy it. Maybe I am lazy or spoiled by rail trails. VERY hilly, with trees I had to go over, under, and around. The trail does go past some very nice ponds, so it is worth a visit if you are a hiker or mountain biker.
Anything less than 5 miles is short for me, so 10 miles round trip. I combined this ride with another in the area near City Island. After driving past this path so many times I sought out the name and finally rode it, very happily. Park at Fort Totten and enjoy the great scenery. Lots of traffic noise near the road, but a small inconvenience for the views.
A hot and humid Thursday in July 2020.
I started at the Kensico Dam in Valhalla and rode this path down to the first ending past White Plains. Twists, turns, over and under bridges and tunnels, it a very interesting and fun place to bike.
Make sure you ride up around the dam, both top and bottom for the glorious architecture, wonderful views and maybe a breeze. There is a quite steep and wide brick path to the right or east side when the greenway enters the park. If leaving the park it is on the left side. You will love it!
My 7yo daughter and I rode the entire trail today (out and back). It seems to be well-maintained currently and we had no issues. It was very enjoyable!
Pros: Long trail with several entry points Mostly smooth Very nice tree coverage Nice trails for off ride riding Decent hills that challenge in a nice way Cons: Dangerous sharp blind turns Some slight ripples pavement at times Several stop and cross points
The MTA has increased their warnings complete with fines for all to stay off the trail. No doubt in my mind whether or not it’s open. https://maybrooktrailway.org/
Just finished a 30 mile ride on the trail. Started by VE Macy Park and ended right before Sleepy Hollow. Nice ride. The first 4 miles were bumpy but as you get further into Westchester the road gets smoother. Nice trail. Next time will ride 20 miles out.
The trail is over 50 miles so it’s tough to give it an overall rating as some stretches rate five stars, and some less than five stars. I’ll try to break down each town, starting at the southern end. I’ll note upfront that the entire trail is paved and well maintained and most stretches can get crowded. And the trail is mostly flat and straight but there are some hills and twists. New Haven: I’ve only been on the section a few times and they’re still working on finishing it. It’s a urban trail with little scenery and lots of street crossings. If you live in New Haven, it certainly is a great place to start a ride. But I wouldn’t go out of my way to ride on it. Three stars. Hamden: Overall, a good section as it is scenic and there’s a 6-7 mile stretch with no street crossings. This is the only section of the trail that is hilly, but they’re mostly short and not too steep. There are a few spots where the trail is bumpy. Five stars. Cheshire: another enjoyable stretch with nice scenery. There are a number of street crossings and for whatever reason, I’ve found the drivers in this area to be overly obnoxious and not letting you cross without an issue. But I could just be my bad luck in the area. Four stars. Southington: the southern end is fine. But I rarely ride the bulk of the trail in Southington. It’s crowded, not scenic, many street crossings, and little protection from the sun or wind. Also, the trail currently ends before I84. One plus is there are spots to stop for a bite to eat. Two stars. Farmington: the newly opened southern two or three miles is wide open with few trees to stop the sun or wind. There’s nothing wrong with it but it’s just not the nicest section. The original three or so miles is a five star section with lots of trees, scenery, and few street crossings. Another plus is you can connect with a 10 mile trail to Canton. Four stars. Avon: the first two or three miles is a great extension of the trail in Farmington. But the trail ends at the Avon public works garage and then it’s cutting through a parking lot, down a road, on a sidewalk, through the police department parking lot, on another sidewalk, and then crossing busy route 10. Overall, three stars. Simsbury: like Avon, a mixed bag. The southern section is going through residential sections, behind car dealerships, few trees, crossing route 10, and riding on sidewalks. Once you hit the downtown area, it improves. Overall, three stars. East Granby: a nice section with some minor hills, curves, open areas, and some flat areas with trees. This is one of my favorite stretches as it offers diversity. Five stars. Suffield: another good stretch. There’s a few spots where tree roots have pushed up the pavement but it’s not too bad. Five stars. Massachusetts: technically, it’s a different trail but it’s really a continuation of the same trail. I think there’s about seven miles currently paved with another mile or so planned. There are a few minor hills and there are some open sections with little sun or wind protection. But overall a nice ride. And this section generally isn’t too crowded. Toss a coin on whether it’s a four or five star stretch.
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