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 Norwalk River Valley Trail. With more than 75 trails covering 520 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 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 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...
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...
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...
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 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 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...
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....
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
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...
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 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...
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...
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...
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...
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...
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...
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...
<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...
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...
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...
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 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 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...
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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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...
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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 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 Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
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 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...
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...
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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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...
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 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 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...
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 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 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...
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...
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...
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 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 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...
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 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 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...
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 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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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 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...
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...
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 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....
My wife and I have been using this trail for years primarily for in-line skating. It is a fantastic trail that is extremely enjoyable each time we are there, however we have noticed over the last few years a real deterioration in the sections in Cheshire and Hamden. The wooden bridges are breaking down that is it dangerous to skate over them, due to the holes that are developing. The inevitable tree roots are getting more and more noticeable and need to be addressed before the ruin the trail any further. The trail needs to be swept and blown regularly, as the stones, gravel and branches all over the trail are noticeable and a hazard to both in-line skaters as well as bikers.
18.35 mile round trip for me from the Cedar Creek Park on the Jones Beach Bikeway connecting to the Ocean Parkway Coastal Greenway at the Jones Beach theater. Beautiful ride, the food stands come in handy too!
We rode a total of about 34 miles,17 miles there & back.. We enjoyed this trail,its different then a lot of trails,you are all over the place,riding in residential,the woods,past the Monrovia Nursery,then into the town..but all on paved ground..Good signage.little bumpy in a few spots,but over all pretty good. Mostly flat with a few small climbs.Would like to go back & finish the trail..
Thanks! to the HVRT for resurfacing some of the trail that the tree roots had pushed up pavement. It was nice to be able to ride without having your fillings about ready to come out Thanks HVRT
We stayed at a very nice little inn called Inn at Twaalfskill that has a driveway that connects to the western side of the bridge on the Hudson Valley Trail. The bridge is a little crowded, so you have to take care, but it is worth the spectacular view. The Hudson Valley Trail on the west side and the Dutchess Trail on the east are both well maintained and less crowded than the bridge itself. HIGHLY recommended. The Inn is a great quiet getaway that could not be more convenient for access to the trails.
The trail offers the opportunity to ride in the green and without cars for most stretches, but its views are limited.
The first part through Yonkers is very uninspiring, it looks more like a landfill than a nice trail, so I would definitely skip that part next time. Coming through those Hudson villages is nice, but it also creates the necessity to cross a lot of streets. That wouldn't have been much of a problem if the trail was designed for it, but the way it is now you need to dismount your bike because the curbs are just too high to bike over, so that definitely takes the flow out of the ride.
Signage is poor at some places as well, I would recommend a GPS unit to ride the whole trail. There are also a couple of unbikeably steep sections that also require you to dismount. The final destination, Croton dam, is impressive to see and the highlight of the route.
All in all a very mediocre biking trail, but options are very limited anyway, departing from NYC. I think I won't be riding it again.
I just cycled the new 2.2 mile Heritage Trail extension from Goshen to Hartley Road. It opened July 18 and today (July 29) I did not see a single person on this section going 4.4 miles round trip . Not one. I feel that the county spent a million dollars paving it just for me. I also cycled to other end at Harriman. This is the easiest 30 miles round trip that one can do. Kudos to Orange County for replacing eroded sections with root bumps with smooth new asphalt (lots of the Westchester rail trails sections need this improving). A review below says the trail isn’t 15 each way. It is. The Harriman to Goshen main trail ends at Saint James Place. There are no signs telling you where to pick up this new section. Common sense tells you to follow where the rail line once was. Hint: Railroad Ave. past the old train station. I had to go through an apartment or condominium complex through an open gate and there it is. Beautifully done. This just adds to the greatness that is the Heritage Trail. It is the best within 50 miles of NYC and NNJ. Dutchess Rail Trail to the Walkway Over The Hudson is the best within 100 miles. The Heritage just ends there at Hartley Road. Goshen has lots of place to eat, though, back in the town. Trailside Treats abuts it and is nice (but doesn’t open until noon).
My wife and I rode this train on 7/27/19. We started at the route 2 park and ride, rode south to a point about 2 miles East of East Hampton, then doubled back all the way to the Willimantic Bridge, finally returning to the car. About 30-35 miles total. Very nice trail, well-maintained, tree lined, rural. Few crossroads, cool, not heavily used the day we were there. Please be aware that while there are no big hills, there are a few long steady climbs along the way, especially East of the park-and-ride; think small elevation with a steady,slow climb All told a great trail, would be awesome during Fall color each season. Please also note that you can connect to the Hop River trail just over the Willimantic Bridge.
This lower section of the Air Line is very enjoyable I know the trail goes North through Willimantic, would be curious of people’s impressions of that section.
There is .5 mile of new trail from Alden's Crossing in East Hampton to the Rte. 66 overpass. There is also a .6 mile extension from the Depot Road crossing to about .25 mile short of the Rte. 66 highway over pass. That leaves about a .25 mile section left to complete the trail so that one can continue to YMCA Camp Ingersol. Once the wetland area bridging is in place, soon I hope (???), riders will be able to go from Portland to Pomfret Center. The work beyond Pomfret Center to Putnam is underway, but far from done.
My son and I traveled from Kingston NY. We went to Harriman to start but there is NO access to the trail from Mary Harriman Park. If you ride out of the park and down the road you can not access the trail because it is blocked off due to a broken bridge and is all grown over in weeds and over growth. We got in our car and went to the beginning of the trail in Goshen where there is a parking lot and the official start of the trail. The trail is great! You take the trail 12.30 (give or take) miles to where a huge fence says "TRAIL ENDS HERE." Therefore this is not a 15 mile trail. It is just over 12 miles one way and over 24 miles round trip. Minus the misinformation at the Harriman end, this was a great trail and I would definitely go back again. It is completely paved!
Heading north from Diddell road is a breeze. Got to the Walkway and were rewarded with a great view and friendly folks! Returning southbound is a little tougher since there is the slight upward grade. Get ice cream or a slice at the frozen caboose!
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