Explore the best rated trails in Port Chester, 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 88 trails covering 580 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 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 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 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...
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 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...
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...
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 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...
When complete the Green Brook Multi-Use Trail will meander for 7 miles through the communities of Plainfield and North Plainfield, New Jersey. The trail will connect major regional trails and parks as...
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,...
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...
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...
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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 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...
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...
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 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 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 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...
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...
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 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...
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 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 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...
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
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 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...
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...
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 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 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...
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 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 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 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...
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 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 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....
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...
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...
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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 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 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...
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 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,...
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 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...
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...
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 complete the Green Brook Multi-Use Trail will meander for 7 miles through the communities of Plainfield and North Plainfield, New Jersey. The trail will connect major regional trails and parks as...
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 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 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 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 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....
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 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 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...
I wish I could give this 4.5 stars.
It is really two separate trails with a five-mile gap. I rode both sections. The bottom section was slightly nicer and might have squeaked out 5 stars on its own.
Most of the trail is shady and scenic. the pavement is generally smooth but a few roots. However, in the northern section it is not really well-marked and a bunch of times I needed to pull out my GPS, either to guess which way to go at a fork or as the poor marking meant I went off trail. The lower section has a part in northern New Haven where it is not kept up as well and there are lots of road crossings.
I love this trail and the scenery. But there is a ditch with a crashed car at the bottom. The car is pretty old. Maybe late 70s or early 80s. It's between the parking space 17 park and ride lot in Monroe and the overpass. There's a green gate blocking the ditch. I would love to know more information about it if anyone knows.
Miles of secluded, smooth, paved trail. We were there on a Tuesday and hardly met anyone. Typical rail trail views with woods and rocks, but the view of the lake and wetlands was very pleasant and broke it up. Surprised to find the white blazes of the Appalachian Trail where it crossed the bike path. Starting in Hopewell Junction heading south east there is a slight incline until Whaley Lake. Not a problem, just made it easier on the way back. After the Whaley Lake continuing south there is a slight decline which did make it a a bit of a grind on the way back but really nothing to be afraid of. We thoroughly enjoyed the day. The only reason I did not give this trail 5 stars was because of lack of and condition of bathroom facilities. When you are of a certain age this becomes more important to you :-) We did the William R. Steinhaus Dutchess Rail Trail, Walk Over the Hudson, and Hudson Valley Rail Trail the previous day, making for a nice mini-vacation. We travelled 3 hours for this trip and it was worth it.
Found a 20-mile gem on the TrailLink app. Great ride until you hit the 6 1/2 mile mark to the 8-mile mark. It’s all mud and horseshit, but I was able to get through it. The first 6 miles are great for the family after that; advance riders only
I have done the trail four times so far, and it is a great experience. I usually take route 25 up to Monroe, hang a right off of 25 to the park, and park my car there. The last leg of the north end takes you to an abandoned factory, and it’s a little sketchy. I don’t recommend it. But if you take the south route all the way down to Trumbull round-trip at 15 miles it is beautiful. The paths are extensive, and as a bicyclist, you could call out to everyone if you were on their left or right. It’s a very safe and fun trail for the whole family.
Some really beautiful areas. But not suited to road bikes!
Skip those two segments. Boring. If you insist on checking those out, do so on a bright, sunny day. They both have a spooky, remote feel.
The trails that have any signage at all are overgrown. The rest is either not marked or unreadable signage. Not even adequate for mountain biking. The only saving grace is the arboretum in Morristown.
Must park on Halpin Rd or you’ll struggle with parking at the trailhead. Slight down hill grade from Ridgefield, but otherwise an easy walk, crossover roads marked well. No bikes just walkers and runners.
I’ve been riding this trail weekly since June 2021. So far, it is relatively undiscovered by users that can make biking treacherous: people walking dogs on leashes and small children weaving across the trail. In July the trail had ripe raspberries all along it for snacking. There are port—a-potties at the parking lot trailheads and even a couple bike service kiosks at a couple parking lots. Some sections of the trail can be quite remote; I’ve ridden miles without seeing another biker/runner. As a female cyclist riding fast, I feel safe, but female runners/walkers may feel safer with a partner. My only critique is that the trail does not connect at the Brewster (east) end with any of the Westchester county trails. But maybe that is coming.
Starting from Elmsford the road has been completely repaired and has less bumps and cracks than before. The path from Briarcliff towards Millwood has been repaired and the road seemlessly transitions from elmsford to Yorktown Heights which is the furthest I have run so far. The important notes: -Well paved for running biking and even roller blading. -signage great but not necessary because trail is clearly designed -only one major road crossing but when I ran there was no traffic -few quick street crossing
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