Find the top rated trails in Westport, 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 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 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...
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...
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...
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...
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 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 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 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 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...
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Much of New York's 15-mile Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest to Monroe. At Crane Park,...
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 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...
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 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...
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...
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
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...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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...
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 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 Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
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 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...
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,...
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 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 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...
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 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...
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 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 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...
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...
Bergen County's Saddle River County Park Bike Path traverses a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. Five park areas are linked by the multi-use...
<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...
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...
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...
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 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...
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...
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...
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...
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...
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...
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 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 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 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...
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...
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...
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 Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
Bergen County's Saddle River County Park Bike Path traverses a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. Five park areas are linked by the multi-use...
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...
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 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"...
This is a beautiful paved trail for biking, running, walking, strollers, and wheelchairs. It is well-kept and offers scenic views--from rolling fields, to bridges, to train cars, to even an old cemetery. My husband and I biked the entire length and back on a gorgeous fall day. It was a really nice ride, but be aware that it is often a false flat trail. One other major thing to be aware of is that you CANNOT access this trail from Mary Harriman Park in Harriman. Your best bet is to access if from Monroe. If heading east on the trail toward Harriman, the trail comes to a dead end fenced off bridge with no access and you're forced to turn around and go back the way you came. Hopefully someday they will fix this and extend it into Harriman for better access. That is my only complaint about this otherwise beautiful trail.
Newly paved trail is now open from the marina to Northern Blvd. This is a great ride especially during the week when it is not so crowded. As another reviewer stated one can extend their ride into nearby Fort Totten.
No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.
Paved path of just about 8.5 miles (all off the regular roadways) provides a great pathway for all skill levels. Beginners can take a leisurely ride with gradual inclines or more experienced riders can challenge themselves with speed and cadence. The path is completely free of roadway dangers as it is only open to walkers, bikers, skaters, etc. It has quite a bit of shady areas to stay out of direct sun due to its location near the woods. Some nice natural scenery. Start/end point located near Veteran Memorial and Isaac Dog Park for other points of interest.
This bike path needs to be Swept with a sanitation truck. Sweeper at least once a month I have gotten so many bike tire flats I usually ride from howard beach to the verrazano and back or I do the 20 mile loop to Rockaway and back home it needs a good cleaning and May be more lighting Thank YOU
In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.
Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.
I just road the Airline Trail across the Willimantic River and then toward the newer ending at Mackie's Ag. Store near the Columbia town line. It was in fine shape. However, what I was looking for is evidence that the work on the Willimantic River bridge was started. I found nothing underway. I road to the easterly end of the Hop River Trail hoping that it was starting at that end. No such luck. Does anyone out there have any information on when this section will be started?
I have been on this trail for the last 10 years. I love this trail just for the scenery and the simple fact that its 10 minute drive away. But I recently discovered that there is a connecting rail trail. This is abandoned Erie branch line in Greycourt that passes through Washingtonville and rejoins the Erie Newburgh Shortcut at Vails Gate Junction in Vails Gate. This abandoned branch line runs directly in front of my house all the way to the orange Heritage trail. So instead of driving to this trail, I can actually can ride my bike and connect two trails.
I am lucky emough to live 1/2 mi from the Farmington Valley Trail and use it quite frequently along with a few of my friends.
I used to ride my horse along this route before it was scheduled for paving for a rail trail. Back then very FEW people used it. Mostly young motorcross kids and horseback riders.
Since it has been paved - horses are now NOT ALLOWED!! (Too bad for us); but as I have moved away from horse riding to personal trail use I am SO HAPPY that I have this wonderful gift in my back yard. There are many many miles and it spans on into southern massachusetts as well.
The trail itself is wonderful; paved, stripe’d and mowed in my area. I have ridden into Mass and south to Simsbury. Before my section was paved I had to load my bike and drive to Simsbury and unload, reload etc. Now, I just hope onto bike (or walk) and go for as long or far as I choose. The scenery is mostly rural, treed and very few homes are seen unless you are crossing streets. I know there are black bears near our home (area) but have not SEEN one ON the trail (daytime use).
It is SUCH a marvelous thing - and I see dozens and dozens of folks biking, walking, & rollerblading. Its a joy to be out in nature!!
Labor Day weekend, 2018
I had a hard time finding the entrance at Swamp Road, it is only marked “No authorized vehicles” and, more ominously, “Police are monitoring illegal activities.” My 7-yr-old son was alarmed and frightened by the signs and the broken down structures, rusty dumped machines and the lack of a path about 500 feet in. Instead it’s a broad overgrown cement yard - too broad to find the narrow throughway to continue south. We rode around a bit on the broken glass and shards, and left feeling unsafe.
I will probably return without him to try again, as I would really like to find a path off the street to get to Trumbull, but I can’t recommend this segment above Pepper.
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