Find the top rated trails in Port Chester, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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 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...
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 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...
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 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...
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...
The South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
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...
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 North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
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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 Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
NOTE: A section of trail from Popamora Point to the Atlantic Highlands Marina has been reopened after storm damage, but the trail is primitive in this section and there may be icy, wet, or muddy...
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
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...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
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...
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 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...
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...
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...
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 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....
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 3.5-mile Middlesex Greenway connects the towns of Edison, Metuchen, and Woodbridge in northeastern New Jersey. The paved pathway, which follows the route of the former Lehigh Valley Railroad...
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 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...
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...
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 Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
<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 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 South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
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 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 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...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
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The Wood Duck Nature Trail, appropriately named for the secretive duck, was made possible through the hard work and dedication of refuge volunteers. This beautiful trail now extends about 1.5 miles on...
NOTE: A section of trail from Popamora Point to the Atlantic Highlands Marina has been reopened after storm damage, but the trail is primitive in this section and there may be icy, wet, or muddy...
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 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 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 is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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 South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, 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 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...
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 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 Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
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 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 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...
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 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...
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...
Thursday, August 09, 2018, 90'F and humid
Yeah, a good ride, which connects via tunnels under the highway to Jones Beach and a more direct connection to the 5-mile bike path that goes north to the mainland. Get sweaty then enjoy the salty ocean beach waters. A go
Thursday, August 09, 2018, 90'F and very humid.
After slogging through the ridiculous Long Island traffic, I rode here and the the other 2 connected trails, which are all nice. You reach the other 2 paths via tunnels under the highway from the Jones Beach parking lots. I have a hard time believing the boardwalk is 4 miles long though. Get nice and sweaty then go in the lovely, salty ocean waters.
This was our first time here, and thankfully it was not too crowded. The foliage cover and the path are incredible, though, so you can enjoy a lot of streams and greenery while walking/jogging/bicycling. For cycling, it’s pretty mild, so if you’re looking for a challenge, this might not be for you. Wonderful family bike morning!
Speeding and unruly bikers come often. Many forgo the bikers' decorum of announcing their approach from behind. " On your left " or "On your right " should be the case, but that is actually the exception. Just be careful if you are walking. It is the only fly in this ointment. The section from Dunkerhook Road in Paramus to the northern end in Ridgewood pleases the sense much.
Great ride but especially by IBM and where there is an active rusty river flowing there needs to be work done.
Extremely steep in some sections (not bike-able), maybe 10% is paved, mostly construction type gravel. Was stuck in the very lowest 3 gears for most of the ride. Did not come across any other bike rider. Not a pleasant ride by any stretch of the imagination. Quite a few hikers though.
We were driving home to PA from CT and stopped to stretch our legs on this trail, so we didn't ride the full length. We started at Goshen and there was plenty of parking in the municipal lot that sits right at the trail head; this was a Monday afternoon, but there was still plenty of parking (thank you to the town for providing free parking!).
The trail is nicely paved and very well maintained. The first two miles were a bit noisy because the trail runs parallel to a busy highway, but after that it was quiet and relaxing. We went a bit beyond Chester and turned around. (Unlike some other reviewers, we didn't find Chester particularly charming.) The trail was flat, easy, well shaded, and relaxing, and we were grateful to the people who keep it in such good condition. Our only (VERY minor) complaint was that close to Goshen the trail sometimes had the feel of riding moguls, probably because tree roots are growing beneath the asphalt. Overall, we would recommend the trail.
After riding, we left our car in the municipal lot and walked two blocks to the Sunshine Cafe. Although the signage made us think it was just a juice bar, it had a nice menu--great paninis and a long list of specialty burgers. We recommend the restaurant highly.
Absolutely love this trail. First off, get there early. Sandy Hook is a popular place and after 9 on the weekends there will be a wait at the entrance to get in.
You can park anywhere and jump on the trail. It's paved and a smooth ride. The view is great and changes from water to trees and back. There aren't really any hills to worry about so it's mostly easy pedaling.
I usually rig a chair to the bike and stop off on the bay side to relax for bit.
I completed this trail this weekend. I started at the entrance of Beardsley Park and ended at Swamp Road in Botsford. The trail is beautiful and very quite. I highly recommend this trail. I would suggest stopping at Pepper Street as a portion of the trail between Pepper Street and Swamp Road is not really a trail. The "trail" is very narrow and overgrown ( I rode through this area with my arms pressed to my sides and still could not avoid the trees/leaves brushing against me). Also, the area has a very high concentration of mosquitos. All in all the trail is AWESOME and I will be riding it (up to Pepper Street) once a week.
After reading some of the reviews I was prepared for a disastrous trail. Yes, its a little bumpy in spots but I felt it was mostly smooth. A couple of places are semi-rough but it wasnt that big of a deal.
Also, getting to it is a little tricky if youre just searching on google for directions. I found the best launch point to be at the northern most end of the South County Trail (just south-east of the Tarrytown Resovior). Drive your car to and get off at exit 23 of the Saw Mill Pkwy. There is a park and ride right there. Park your car and head south on your bike for the South County Trail and North for the North County trail.
I always attempt to start at one end of a trail and ride it to the end. According to the description the trail starts in Harriman which may have been the case at one point but as of July 2018 is not so. As others have said the trail ends abruptly at 12 miles and does not go to Harriman. I'd recommend you start at Crane Park in Monroe, it is easy to find and offers plenty of parking.
As far as the trail itself the scenery was average. The trail itself is all paved and mostly flat so it made for easy riding. The towns off of the trail are very quaint, I'd highly recommend walking around Goshen and visiting Chester for its local brewery. If you'd like to extend your ride try to find the unpaved extension in Goshen. It is single track and about two miles long so I'd take a mountain or hybrid bike.
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