Find the top rated trails in Fairfield, 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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Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
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Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
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...
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....
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 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"...
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 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...
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...
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 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 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 Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
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 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...
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 delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...
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...
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...
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 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...
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
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 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...
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...
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 Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...
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...
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...
Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
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...
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
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...
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 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"...
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...
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 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 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...
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...
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
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...
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
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 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...
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....
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 High Line rail-trail is an urban marvel, stretching 1.5 miles and towering almost 30 feet above street level through several neighborhoods in the lower west side of Manhattan. The first section...
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...
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 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 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...
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 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...
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...
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...
Hi All,
Per "Record Journal" Newspaper New Section of "Farmington Canal Heritage Rail Trail" (Curtiss St & Kane St) to Lazy Lane. Happy Trails, RVC (tn) "Zenith"
http://bronx.news12.com/story/36390645/mta-will-add-bike-racks-to-bx23-q50-buses
I love to ride the bike path early mornings or late evenings. Walkers, etc please stay to the right of the path.
The 0.65 mi. extension of the trail from Curtis St. to Lazy Lane is now open although the connection from the old end of the trail at Curtis St. still requires crossing a tricky intersection. Lazy Lane is now the best place to start in Southington as there is a big new parking lot and that location provides easy access to and from Rt. 10 off the I-84 Queen Street exit. It is now 8.5 miles of continuous very well paved and completely off road trail from Lazy Lane in Southington to Rt.68 (West Main St.) in Cheshire. If you take the short .75 mile ride down Willow St. off of West Main St. to the Cornwall St. entrance of the trail you can get back off road very quickly. I rode the first .75 mile section of the trail south from Cornwall St. to Higgins Road to make it a nice 10 mile one way trek from Lazy Lane but I was surprised to see how many cracks there were on this part of the trail. They were all pretty much filled in but since they are very frequent and extend completely across the trail it was not very comfortable riding for a road bike. In contrast I don't recall seeing a single divot on the 8.5 mile section from Lazy Lane to Rt. 68. Another interesting aspect of this 10 mile section of the trail is that the first 4 miles headed south provides no shade at all in the September mid-afternoon and then the next 6 miles starting at about Rt. 322 is almost completely shaded. On a nice mid-70's afternoon that lack of shade in the beginning was actually very comfortable but I imagine it is kind of hot on a mid-summer afternoon. The contrast between the 2 sections of this 10 mile route makes for a great ride as those changes also parallel the route starting urban and turning almost rural by route end.
Was searching high and low for a long trail like this for long runs. Went here for the first time this past weekend and it completely surpassed any expectations I had. Everyone was super friendly! The views were amazing. Will be even more beautiful in the fall. Can't wait to keep running here and bringing my dog along as well!
I think this trail is fine for local people who want to get a little exercise and bike through town. But it's not a trail you drive to for a scenic ride and it's not good with kids.
We parked I guess midway, in area the Greenwyay's facebook page directs you to. In a few blocks it turns into a sidewalk with a lot of strip mall driveways. the other way, the trail petered out onto a residential street after a few blocks. By myself I might have followed it to see if it became a trail again. But I didn't want to bike on the busy sidewalk or on the street with my kid. Also, the hills are not long but they are steep and challenging for a kid who is still on a bike with 20" tires and no gears. So we gave up. Wish trail link would have a category up top that defines trails as scenic "destination" rides or "getting around" local rides. It would have saved us a lot of time.
The part that goes through Beacon Falls is about a half mile long and it goes along the river, yes, but on a sidewalk through a not particularly charming town. The part in Naugatuck is paved for about a mile through a park and then turns to dirt, not suitable for a road or hybrid bike at all. Neither section was really worth the time it took to take our bikes on an off the rack.
They added almost 2 miles from monroe to Harriman!! Nice new paved trail
Hey, this is a well-maintained, wide asphalt path and fine for their community. As the description stated, it is "hillier and more winding than a typical rail-trail," so take that into consideration. I am spoiled by rail trails, but am glad I did it once, but would not travel an hour and half again. If you're in the area or within half and hour drive it's very fine.
This is a hybrid/mountain bike trail. Great riding experience.
Great ride from Nyack to Haverstraw and back, this is a hybrid/mountain bike ride...leave the road bike home. Scenic.
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