Explore the best rated trails in Fairfield, CT. Whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail. With more than 70 trails covering 506 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 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...
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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 two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
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 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...
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...
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 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 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...
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 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 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 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 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...
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 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...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
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 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...
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 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 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...
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
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...
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...
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...
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...
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...
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,...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
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 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...
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 two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
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 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 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...
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...
<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 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...
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 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 Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
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...
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 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 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...
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...
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....
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...
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 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 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...
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 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 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 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...
Clean paved trail behind the high school. Great for biking.
My wife, dog and I ride the trail nearly every day. The Hartley road entrance is a bit tricky but once you figure out how to get to in its a piece of cake. Hint...when you get into Goshen and get to the end of the first part of the trail follow the dirt path to the fence, there is a gate, be courteous and shut it behind you and ride thru the development and you will be in connect with railroad ave and see the connection for the rest of the trail. Enjoy!!!
Enjoyed a ride from Simsbury past the Mass line and back. As always, well maintained, a few frost heaves here and there but nothing major. As we were riding we noticed some trail widening in progress in Simsbury/Granby. The area across the Mass line is very well maintained and passes some fields and a nice golf course. Thoroughly enjoyable!
This entire trail has been paved for years.
This is a great, scenic route that weaves its way through at least 3 different parks in the area, and under quite a few bridges. Mainly flat and most of the trail is covered by nice tree canopy to keep you shaded. We had a great time traveling the entire length of the trail (and back) today. However, that said, I do have to agree with some of the other posts on this site...the path can get a bit congested in areas (like the trail head by the duck pond, and as you ride through the parks). This is the only reason i didnt give a 5 star review. A lot of the walkers didnt honor the keep right except to pass rule, others walked 2 sometimes 3 abreast taking up the majority of the pathway, and still others stopped in groups in the middle of the trail. My advice would be to hit this on off peak days/hours, but if you do go on a weekend or holiday, and your on a bike, just make sure you announce yourself and advise those in front of you that you are passing on the left. The majority of trail users were considerate and moved over to the right when needed. All in all, it was a great ride, and i would recommend it to beginner to intermediate cyclists.
It’s mostly flat and has lots of great scenery, especially towards the south of the tail. I biked with my friend for 7 miles before we realized it would take another 7 to get back to the car. We loved it anyway! Great workout without feeling you worked out!
We just finished riding this trail yesterday 9/9/19 and we have to say this is the best maintained paved trail we have ever rode our bikes on.
We started from the southern endpoint in Hopewell Junction and rode the trail to Poughkeepsie where we rode over the Walkway Over The Hudson on onto the Hudson Valley Rail Trail to New Paltz. There are train stations along the way where you can sit a a picnic table and eat or you can try one of the food trucks at the walkway before or after crossing the Hudson.
The trail is wide with plenty of room for three bikes to pass each other and there are not too many road crossings and none of them are busy roads. The thing that stood out to us as we rode was the trail signs directing you to the different points and the entrance and exit ramps to the many parking areas and local road access points along the way with the many benches to sit if you want to take a break. The trail is mostly wooded and there is not much to see as far as scenery but if you looking for a level smooth place to ride, this trail is a great choice.
This trail is just 1.2 miles from our home and is by far our favorite trail to ride. We enter the trail at the northern endpoint in Dutchtown in Haverstraw and ride to Nyack Beach Park and back. The 12.3 mile ride can be done in less then an hour or you can ride up the mountain and include the loop around Rockland Lake State Park where you can also park and enter the trail from. This trail winds up and down along Hook Mountain State Park with views from high over the Hudson River and then down along the rivers edge to Nyack Beach State Park. If you can get out during the week you can have the trail to yourself. Hybrid or mountain bikes are the better choice but you can make the trip on a road bike if your carful. If you live in this area you shouldn't miss this hidden gem.
We have biked this trail numerous times over the past 7 years and it's one of the trails we always go back to. We usually start at the Millwood parking lot and head north. The bridge over the Croton Reservoir is the highlight of the trip. There are horse farms and wooded sections along a rock gorge before you merge onto the Putnam Trailway. The trail is crowded on weekends so if you can get away during the week you will have this trail to yourself pretty much until the afternoon.
September 5 2019. Best Rail to trail we have ridden on. We started at the parking area in Hamden and went north 12 miles. Most of the trail was smooth as fresh tar. We almost did not do this trail because of the reviews but they were wrong. If you like smooth riding and well marked, this is the trail for you
Not smooth roads from 79th Street towards 125th Street. Narrow areas.
After 141th Street....some roads are not smooth.
Due to the fact that roots, heat, rain and etc..causing to crack and rise.
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