Find the top rated bike trails in Fairfield, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
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 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...
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 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 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....
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...
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...
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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 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 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 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 Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range 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...
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...
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...
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 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 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 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...
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 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...
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 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...
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 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 Maybrook Trailway is a paved multiuse trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
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,...
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...
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....
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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...
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...
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...
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...
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...
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...
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 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...
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 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 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...
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 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 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 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...
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...
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 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 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...
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 Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
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 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 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...
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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...
I have yet to find a similar trail since I moved to NJ. I am always trying to get back there!
I visited this beautiful, peaceful trail today for the first time. I started out at 11:45 this Sat and enjoyed every minute. The trail is quite and with relatively few people. Highly recommend!!
This is not really a one long trail but a series of segmented trails. While the beginning of each segment is marked with an "OCA" post, at the end of most segments there is no indication about where to find the next thread of the trail. Often you have to go through busy suburban streets to make the connection, some of which are quite dangerous. Other reviews recommended using GPS on your phone, but Google maps only indicates where the various trail segments are and it is difficult to find out how they connect. My friend & I attempted to do the northern half of the trail from Tarrytown up to the Old Croton reservoir. When you get to the Clearview School in Scarborough, you have to ride on a very busy Rt. 9, which has no shoulder, until you can take up the trail on Scarborough Rd. When we got to Ossining, the trail ended with no indication how to continue, so we again had to ride on Rt. 9. Then my friend hit a broken drainage grate on the side of the street, which was covered with leaves so that she could not see the gap in the pavement. It threw her head-first onto the asphalt. She was knocked out for several minutes, had a concussion, was bleeding profusely and nearly broke her neck. I called an EMT which took her to a hospital, where she stayed for two days and had stitches to her face and several tests. She was lucky she was not paralyzed (thanks to wearing a helmet). Exercise GREAT caution if you take the Ossining part of the trail. Some of the other segments are O.K. but some of them are just like riding through peoples' backyards.
Renovation wrapped in early November. The revamped and now paved Jones Point path is great, used it today. Quiet, scenic, and much gentler than the steep up and downs on the parallel segment of 202/9w. This makes the 9w corridor my favorite way to bike to Bear Mountain overall now. It's that good.
Great walk. But the section north of Woodhaven station is a dead end. I had to go back and walk city streets for a long section. All in all great walk from Soundview ferry station in the Bronx to Bronxville train station. I will return fir the next section
I have been riding this trail for years. As of November, 2020, a wonderful new section has just been introduced, stretching from Millerton, NY to Under Mountain Road. This means that the trail now covers almost 24 miles one-way from Wassaic NY all the way to Orphan Farm Road near Copake. This is a classic, beautiful trail the runs through a valley, with so many nice sections: tunnels of trees looking out over farms, places to stop in Amenia and Millerton, a section that runs right to the entrance of Taconic State Park, several raised ridges with views of fields on both sides. The newest area, from Millerton to Under Mountain Road, is perhaps the nicest of all, as it runs through an area with views of the Taconic Berkshires and runs over multiple ponds via the old train bridges (now updated for bicycles). I’ve been on rail trails all over the northeast, this is one of the very best.
The Air Line State Park Trail is one of my favorite bike trails in Connecticut. Rode our bikes there last week and was very disappointed with the recently resurfaced section from the Cranberry Bog in East Hampton. The gravel that was used in the resurfacing is to soft and to deep. Has only been open for a week (10/28/2020) and it is already marred by craters from horses and foot traffic. The ride is bumpy like a wash board. At one point I swerved to miss a pile of horse droppings and got to close to the edge which then collapsed under my bike causing me to fall. What was once a favorite section of the trail for us, is now a major disappointment.
this is newly opened (was still closed when i checked in august at least) and paved and it is magical :) biked it today
Great trail. Southern section paving is beautiful. Trail is clean with surprisingly little litter or debris. Some sections in southern Westchester seem like they laid pavement directly on top of the old rail road ties, but newer sections are very smooth. Safe for family rides with minimal road crossings. Mostly flat or shallow grade (up to 100’ per mile). Beautiful scenery through parks. Too bad that this route does not continue South through Van Cortlandt Park and connect into the bike networks of Manhattan. (About 2 miles away.) Some sections are very near the Saw Mill Parkway and Major Deegan. Parts of the Saw Mill / Bronx River still need cleanup. And access points in southern Westchester to the towns are not great. (Be prepared to street ride if you want refreshements.)
This trail is an easy ride for everyone. It’s well maintained with plenty of benches to rest and a mixture of sun and shady spots. The end of this trail leads right into the Walkway over the Hudson.
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