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 84 trails covering 539 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 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 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 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...
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 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...
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 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...
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 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 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 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...
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...
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...
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 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....
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 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...
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...
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 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...
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...
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...
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...
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...
<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 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...
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 Berkshire Valley Management Area Trail passes through hardwood forests and affords views of the valley below to the right. Equestrians must have a NJ Wildlife Permit, which is available from NJ...
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 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 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 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...
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 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....
This trail is in an area rich in geological history. Zinc and Iron Ores were transported along this branch from mines in the area that operated for over 200 years. The trail is scenic with a slight...
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...
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...
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 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...
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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...
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 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...
This trail is in an area rich in geological history. Zinc and Iron Ores were transported along this branch from mines in the area that operated for over 200 years. The trail is scenic with a slight...
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 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...
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 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 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 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 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...
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 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...
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A short rail trail with two covered bridges occupying a portion of the former Mount Hope Mineral Railroad right-of-way in Wharton, NJ. In the future this trail will be linked with the Rockaway...
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 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 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...
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 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...
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 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...
My favorite trail for nice long walks. Beautiful views of the hudson.
Fun park for walks. Has fountain and ducks and paved trails for walking biking or running
Plenty of curves and turns not to mention hills. Visiting from Florida and fairly new to cycling so the hills were a good challenge! Most of the street crossings have detectors that automatically stop traffic. Good signage for approaching hills. Pavement in excellent condition.
The trail along the boardwalk has been extended west by an asphalt path to the west end and to the nature preserve.
Perfect walk for our standard poodle. Just the right length. Friendly people . A few hills
I have biked about two-thirds of this trail, and it's great. There are several access points, and many places where you can exit the trail to ride on local roads.
I parked at the westernmost parking area and rode west. Nothing much to see (other than the Orange County prison) and fairly populated on a Monday.
I then rode East towards Goshen. Just before the town, a resident has put up several "No Trespassing; Private Property" signs and the trail is no more although the map shows it jagging left and coming back into town.
What you have to do is ignore the signs for about 10 yards and make a u-turn onto a road that leads up to West Main Street. Take that through town to North Church and then to St. James. You'll find the rest of the trail headed to Harriman.
The trail is excellent and well-maintained. I only went as far as Chester. That will be my starting point next time. From Goshen to Chester there were a lot of walkers and dog-walkers -- all extremely polite and practicing trail etiquette. It's a little too tame and populated for my taste, but I am guessing as you go further east, it is less so.
I will be returning.
My wife, dog and I ride the trail nearly every day. The Hartley road entrance is a bit tricky but once you figure out how to get to in its a piece of cake. Hint...when you get into Goshen and get to the end of the first part of the trail follow the dirt path to the fence, there is a gate, be courteous and shut it behind you and ride thru the development and you will be in connect with railroad ave and see the connection for the rest of the trail. Enjoy!!!
Beautiful in fall, but a workout going from Brewster. A few major hills.
Enjoyed a ride from Simsbury past the Mass line and back. As always, well maintained, a few frost heaves here and there but nothing major. As we were riding we noticed some trail widening in progress in Simsbury/Granby. The area across the Mass line is very well maintained and passes some fields and a nice golf course. Thoroughly enjoyable!
Been on this trail many times! Will return!
Some sections are worse than others with tree roots under the pavement, signs are not located thru Matawan, (train station, etc.) need clean bathrooms along the route.
Recommend!
Beautiful scenery. (some points you can see NY!)
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