Explore the best rated trails in Westport, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Ridgefield Rail Trail. With more than 81 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 Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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 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...
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...
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 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 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...
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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 William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.1-mile trail runs through what seems...
The Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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...
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 Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
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 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 Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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 Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
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...
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...
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 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...
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...
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 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 Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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...
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 Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
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 South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...
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...
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 High Line trail runs 30 feet above the bustling Manhattan streets and sidewalks below, which for trail lovers makes it an attraction in the same league as the Statue of Liberty or the Empire State...
The Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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 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...
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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 North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10-mile multi-use recreational path and runs along the former Wading River railway corridor in Brookhaven—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...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees 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 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 Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
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 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...
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 Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
The Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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...
Pretty, shady, flat. Connected to Duchess Rail Trail and went all the way to Walkway over the Hudson.
I rode south then east from rt. 8 in Poughquag. There is a small missing section above the Croton River east branch in Brewster . You can walk your bike along RR, via open fence for this 50 yards or so or cycle downhill on Peaceable Hill rd and up the hill on East Main to get back on. The TrailLink map (as of 8/3/22) shows the trail ending here. But it continues a few miles east into Connecticut. About a half mile over the line to an overpass at Mill Plain Rd in Ridgefield CT. Smooth all the way with terrific scenery. Many lakes.
It's a shame this path is not well maintained. There's also a lot of speeding ebikes, so be careful!
Beautiful ride from north of Van Cortlandt part to Mahopac.Well paved and maintained.Connected to the North County trail And the Putnam trailway
I never met a rail trail I didn’t like until today. Challenging hills is an understatement for those of us seniors used to railroad grade only.
Not a portapotty for the 7 miles north at the trailhead. Check that trail off our list.
Excellent trail, nice for a walk, run or bike. Beautiful area, pleasant folks. Good for families but watch out for serious cyclists when you have small riders.
Technically not for bicycles. But you still can ride if you want. On a weekend day I saw only 3 people went on a walk. Keep in mind that your bike might be dusty after the ride since there is no regular asphalt.
we’ve only done less than 16 miles total at north end, but really enjoyed it, yes, it’s dirt/crushed gravel, but mostly smoother than some asphalt sections elsewhere. We currently have hybrid road bikes. Pomfret pavilion park is cute and Towns of Pomfret & Woodstock are extra beautiful. Trail is woodsy and shaded, saw turtles and hawks. Ate at Vanilla Bean Cafe in Pomfret which was very busy, lots of outdoor parking and sports or hot rod cars and motorcycles to ogle at, great cake. Nice parking lot at south end of Thompson section. Bring lots of bug spray in July, though.
Started at parking lot near Simsbury Airport and went north to the end (including the Southwick Rail Trail & Columbia Greenway Rail Trail) in Westfield - 30 miles r/t. Trail surface is in great shape with road crossings all well marked and navigated. Lots of country & wetland views, well shaded and moderately traveled (a nice summer Saturday) w/ plenty of portapotty & bench stops along the way. We were on our E Bikes. Wife rates this as a "we will be back" trail even with the hour car trip.
7/9/22 - 85F, partly cloudy, windy
I wanted to go check out the Airline, Northern section - I’d heard things were happening over the past few years, but I hadn’t been out there in a few years.
Well, yes! A few things have changed greatly for the better. I parked at the Pomfret Train Station and instantly noticed that there is a beautiful new bridge over Rte 169. Nice Job CT Dept of Energy and Environmental Protection (CT DEEP)! Very pretty (I didn’t take a photo, but there is a photo on Google Maps). I had high hopes for the trail surface northeast bound, but as a couple of reviewers have mentioned, it is still pretty rough. I was riding a gravel bike with 42mm tires, softly inflated, and didn’t have much trouble, but this section would be much more joyous on a fat bike or suspended MTB with 2.5“ - 4” tires. There are long stretches of nice dirt double track, but it periodically degrades into 1.5” “crusher run” gravel for some stretches where CT DEEP has put down some fill to stop erosion. Well done, this was definitely needed. The road crossings have been greatly upgraded. Eastbound riding toward Putnam, there is now a beautiful new overpass at Day Road (I think that’s the name), Wright’s Crossing is a grade crossing with a marked crosswalk, and then there are beautiful new culverts at Holmes, Modock and River Rd., and another marked grade crossing at Town Farm Rd. After Town Farm Road the trail continues, but then just short of the Quinebaug river…it just ends with a pretty big drop off to the access road for the Town of Putnam Waste Water Treatment Plant next to the Quinebaug River. I know from previous rides (and other reviewers have mentioned) that there is a nice bridge across the Quinebaug which can take riders into Putnam (ice cream, coffee shops, hot dogs) but there is giant “disconnect” in getting to this bridge from the trail.
The trail surface between the Pomfret Train Station and Putnam, however, is evolving. As I mentioned, in more than a few spots it is very rough. The grade has all been cleared and drainage provided so it stays relatively dry though. This is a huge improvement from the last few years when, by any assessment, long sections of the trail were completely impassable and those that weren’t were overgrown, rough, wet, bug infested muck holes. I’m sure that CT DEEP is working on improvements as budget and staffing permit, so I’m not going to whine, however, if you go, take a fat bike or mountain bike. Don’t need to mention - there are no services after leaving Pomfret, so bring everything you might need or want, including a charged phone, and insect repellent to ward off the mosquitos later in the afternoon.
CT DEEP and Ashford, Pomfret and Putnam Depts of Public Works have obviously been spending some cash on this trail, and I for one, am happy about it. Just need to improve the surface a little, and make that connection to the Quinebaug Bridge in Putnam. These improvements will continue the evolution of the Airline Trail to be one of CT’s and the nation’s best
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