Explore the best rated trails in Greenwich, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Norwalk River Valley Trail. With more than 86 trails covering 567 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 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 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 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...
Running alongside a New Jersey Transit passenger line, the Traction Line Recreation Trail has been around since 1986, when Jersey Central Power & Light donated portions of the land to the Morris...
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 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 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...
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 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...
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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...
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...
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 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 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 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 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 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...
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 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....
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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...
Running alongside a New Jersey Transit passenger line, the Traction Line Recreation Trail has been around since 1986, when Jersey Central Power & Light donated portions of the land to the Morris...
The Maybrook Trailway is a paved multiuse trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
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...
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 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 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...
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 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 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 Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
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...
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...
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...
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...
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...
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 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 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 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...
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 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 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...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
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 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 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...
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 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...
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...
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 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 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 Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
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 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 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 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 system of trails in Loantaka Brook Reservation are open to hikers, cyclists and equestrians, although the trails are marked as to which uses are permitted on each segment. Loantaka Brook...
I recently moved to Dutchess County from Long Island. A neighbor took me to this trail and I continue to go there as often as I can. Whenever I have guest or family to visit I always suggest we go biking there. If you are riding from the east side of the bridge you’re riding uphill slightly. On the way back there’s a lot of coasting which is very refreshing after crossing the bridge. Spectacular views from both sides. It’s a very easy ride. Plenty of parking and there’s also an elevator you can use to get up to the bridge. I highly recommend it.
Its my kids 1st trail bike experience, they enjoy the trail so much and they want to comeback for another ride
Road this trail yesterday end-to-end as an out and back starting from the new trailhead parking area in Harriman at the intersection of River Road and North Main Street (portable toilet and bike repair station available).
With the two newer sections at either end the trail is now fully paved for 18.5 miles.
At the current trail end at Palmer Avenue in Middletown there are some signs that the trail will be extended further but no current activity.
The trail is in great shape but could definitely use better signage to help navigate through Goshen. My advice is to use West Main St. as a connector.
The Korean War Memorial in Airline Park in Monroe is worth a stop.
Awesome trail. Mostly covered by trees with a wide paved surface. All kinds of folks and wildlife on the trail. Did it 3 times during the week, so no idea what’s it’s like on the weekend. Lots of parking along the way. Multiple benches if you run out of steam or just want to sit. Certainly a “gem” in an area with lots of car traffic. Some busy crossings but cars all stopped to let me go.
Was really surprised as to the condition of trail, was great. The only thing that would be great to see would be mile markers. As a resident of the area was looking forward to when trail would be black topped, now that it is completed its great to ride with a trike, Thanks
After many years of driving over an hour from NJ to Turner st in Hopewell Junction to ride the Dutchess trail to Walkway Over the Hudson - it was fun to go south / east in the other direction. I rode about 14.5 miles from Hopewell Junction to Holmes, a mile or so past Whaley Lake. That's roughy half of the Maybrook trailway . 29 miles round trip on a perfect day (7/22/21). As someone noted it is uphill 13 of these 14 miles. But hardly noticeable. Since the locomotives can't manage hills, the railroad builders levelled the right of way. Here with the existing track next to you - you're assured of no steep hills whatsoever. About 65 minutes to the turn around point, very leisurely done but flew back to Hopewell Junction at 17 mph and 40 minutes.
Will explore the other half next week starting in Brewster. I expect it to be just as enjoyable as this was.
Recently repaved in sections, but done sloppily and left bumpy. The northern half of the trail has a lot of sunken and washboard sections that make it unpleasant to ride. From Van Cortlandt Park and about half way up the trail is nice, but from mid-point to where it connects to the north county trail is a mess.
As described, this trail varies from a wide gravel path to a single track dirt track with grass. We started in Tarrytown and went south. This is not a trail for a road bike but you are ok on a gravel bike as long as you are comfortable with rough spots and roots. The trail has lots of road crossings and they vary from neighborhoods where the cars have stop signs to steep hills where no one stops. Almost all have large granite curbs that you have to dismount to lift your bike over. As long as you are cautious you are ok. We made it to Yonkers when we turned around due to a raccoon which was blocking the trail and threatening to attack. Others on the trail kept going and one group was going all the way to NYC. We rode a bit of the River Walk as well which looks like it connects the southern part of this trail with the northern.
There is a bathroom at the Keepers House along with a museum and lovely docents who had lots of fascinating information about the aqueduct.
This was a fun outing to try something new but will likely not be on our list of gravel trails we love to ride and go to frequently.
Paid $3.50 parking at Metro on weekday; suggest you park free at the Pete&Toshi Seeger Riverfront Park next door, north. Klara Sauer Riverfront Trail ends south at Dennings Point State Park which on a map shows a 1.2 mile loop trail. Caution: Only the riverfront half of the loop is accessible and only by walking - at some parts too narrow a path for bikes. The 2nd half of the loop is now an ESTUARY. The weeded, rooted, overgrown remnant of trail is trouble for anyone not heeding the warning signs to turn back.
Rode from Harriman through Goshen in to the new about 3 and half mile section, from Hartley Rd to Palmer Ave in Middletown. This section as of now (7/6/21) is not on the map here but it exists and is very nice.
5 miles of hilly terrain along the river from Nyack to Haverstraw that consists of mostly stone dust with some asphalt. A couple climbs and descents are steep but not a problem for more experienced riders. If you are going to attempt with a road bike go with a bigger tire. The 28mm Armadillos worked well for me. Watch out for pedestrians, especially on the downhill sections.
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