Find the top rated walking trails in Westport, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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...
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 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...
New York City's East River Greenway offers views of the East River, Queens, Brooklyn, and the iconic bridges that connect these boroughs to Manhattan. The paved pathway traces the waterfront on one...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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...
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...
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...
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...
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...
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 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 Essex–Passiac county...
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 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 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...
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...
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...
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
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 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...
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...
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 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...
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...
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 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...
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 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...
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
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 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...
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 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 Essex–Passiac county...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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 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...
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...
<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 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...
Hudson River Greenway provides a continuous 11-mile route between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes...
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 Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
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...
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...
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 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...
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...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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 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...
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...
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.
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.
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.
My husband and I checked out this trail for the first time on 7/29/2018. It was a Sunday afternoon around 4:30 p.m. and the weather was gorgeous, bright and sunny. The trail has some really beautiful sections and some very secluded sections running through urban neighborhoods. At some points, it was so secluded that it felt like it could be opportunistic for crime. There was literally nobody around, it was kind of eerie. My husband commented that he would not feel comfortable with me riding this trail alone.
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.
From Wassaic to Copake, free parking in Wassaic train lot on weekends. Goes through a few small towns with bike shops including one in Copake. Lots of places to eat in the towns, some country roads tie the rail trails together, a few hills but nothing brutal, beautiful lake, plains, and frams views, and if you don't mind a small hike, check out Bash Bish falls in copake, worth the hike.
Closed for two years now, to all traffic from marina to Northern BLVD
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