Find the top rated trails in Darien, 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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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 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...
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
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 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 Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
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 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...
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 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 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 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 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...
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...
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...
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...
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 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 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 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 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...
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 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...
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...
The Pequonnock River Trail—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching...
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 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...
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...
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...
<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...
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...
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 Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
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...
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 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...
At 2.6 miles, the Staten Island Greenbelt Multi-Purpose Trail offers a nice jaunt for joggers, walkers, and cyclists alike. The crushed-stone path is 6-feet wide and runs from Rockland Avenue to...
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...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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 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 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 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 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...
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 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 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...
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...
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 Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
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 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 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...
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
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 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...
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...
The stretch between Verrazano Bridge and Ceasar's Bay Shopping Center along Gravesend Bay is riddled with thousands of cracks and holes causing flat tires. This Bike trail has gotten worst ever since Hurricane Sandy hit the shores in October of 2012. Bike, Walk, Jog at your own risk. A disgrace for New York City.
Wonderful little trail...little bit on the residential side....but nevertheless wonderful. Very disappointing that we don't allow bicycling....nasty anti-bike sentiment among the comments. Lots of no-bike paths in Florida.
Love walking this trail - it's an easy walk from one end to the other and back but combine it with Lene Lenapi trail at either end to add distance and difficulty. It's in a populated area but set back enough that you don't feel like you're "in the city"
Warning as of 6/13/17: There's a large tree down across the trail just after the Pompton Ave bridge on the western side. It's possible to climb over the trunk but bikers might have a little trouble. Use caution until it's cleared.
I enjoy a good ride, but also am looking for a good place to train. I rode from the RT 117 junction north for about 10 miles. The trail was much bumpier than I was used to. There is a clear knowledge of the state of the trail, the larger bumps and potholes are sprayed and there are signs warning of 'uneven pavement' but it was not super enjoyable to ride on at higher speeds. My biggest concern is the RT 100 section. There is about a 1 or 1.5 mile stretch where you are on the shoulder of RT 100. If you ride out and back you end up having to cross 4 times, once at an intersection, with all others being at crosswalks with no lights or markings. Although the shoulders are wide they are filled with gravel and pot-holes forcing you to ride closer to the shoulder line than preferable or risk a flat. Additionally, you have to cross an on-ramp/off-ramp to stay on the shoulder. All told its a bit to dangerous for my taste. The section starting at Millwood and going north seemed nicer. Ill probably try again parking up there and going all the way onto the Putnam Trail, but I don't know if its worth it to ride the RT 117 to Millwood section again.
Great ride for any type of bike. The extension mentioned in the previous comment is basically completed except that there is a break due to seemingly never-ending construction on the Orangeburg Road overpass.
You can ride the new section from the Blauvelt Library to the overpass and detour on streets to meet the older part of the trail.
I've ridden and walked this trail many times as I live near here. Great trail with nice river views. In my opinion not really suitable for road bikes. The old Piermont train station is open on weekends and is worth a stop.
Took my brand new bicycle on its maiden voyage on this trail. It was great fun. Rode for about 3 hours and loved every minute of it. The historic information posted along the trail is nicely done. The fact that there are restrooms at the trail head is fantastic! They really did a nice job with this trail. Highly recommend it for all. Very kid friendly.
I rode this trail yesterday in combination with the Walkway over the Hudson and the Hudson Valley trails. Started in Hopewell Junction for a just about 36 mile out-and-back.
Great rides all the way!
The Walkway is spectacular (even on an overcast morning)!
The transition between the trails is seamless.
Informative signage, especially on the Walkway Over the Hudson and Duchess trails.
I love cycling here in the winter and off peak times. I ride here week nights because close to home. Pedestrians are clueless, make no effort to stay right walk dead center of the path and don't know how to move right when someone yells "on your left". On the weekends its an obstacle course of entitire families astrollers and dogs. Stay away
Dateline: Monday April 17, 2017. Weather 68' F, sunny with scattered clouds, a slight breeze.
It was a beautiful first ride of the year, with many more to follow. This short asphalt paved trail is fairly level and goes through beautiful county, including farms, forests and close-by streams. At each end there is a nice village, Walden and Wallkill, that you can visit and get a refreshment.
I did start the northern section, but did not complete it because my hybrid bike's tires are not good for such a rough path. When I get my other set of wheels back from the shop for truing, they have have off-road tires that will better handle trails such as this one. Too bad though. I have already completed the northern end of the Wallkill Valley Rail Trail and hoped to keep connecting the different sections. Another time.
I go far distances and other states to spend time exploring different bike trails. It took my a little more than hour to visit the Putnam Rail Trail. This was the hilliest ride outside of mountain biking that I have done, yet the scenery was superb. Lots of lakes and reservoirs. Despite the 95-degree heat it was my favorite bike ride last year.
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