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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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 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 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...
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...
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...
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 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 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...
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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 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...
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 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 William R. Steinhaus 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...
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 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...
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 Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
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 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 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 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 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 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 paved pathway running through West Hudson Park offers a scenic, tree-lined escape in Harrison, a suburb of Newark. The trail provides access to the park’s stocked lake, water park, athletic...
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 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 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...
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...
<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 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 Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
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 William R. Steinhaus 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...
The delightful asphalt Middlebury Greenway winds 4.5 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
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 Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights 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...
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...
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 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 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 trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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...
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...
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Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...
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 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...
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 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 paved pathway running through West Hudson Park offers a scenic, tree-lined escape in Harrison, a suburb of Newark. The trail provides access to the park’s stocked lake, water park, athletic...
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The Patriots' Path covers roughly 35 miles of terrain and is open to mountain biking, horseback riding, cross-country skiing and hiking. The multi-use trails links parks, open space, recreational...
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...
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...
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...
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...
Canopied with deciduous trees for most of its 10.8 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 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 William R. Steinhaus 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...
We have ridden this trail before, and really enjoyed it, especially the part near the ponds below Oxford Airport. We expected it to be somewhat rough, and we are always willing to walk through particularly wet/mucky areas and to put up with rough stretches. However, the trail has really gotten much worse. After about 2-2.5 miles in, it became extremely sandy/silty, and we could only ride on the narrow edges. Then at about 4 miles in, there was a stream flowing through the whole trail, with nothing but mud and muck; no way to ride through, as it continued as far as we could see, so we had to turn around. End of ride for the day...
The OCA trail offers a rich variety of surfaces and surroundings. I rode a commuter bike with 38mm slicks and did just fine, even through the muddy sections. I picked the trail up in Yonkers off the South County with a bit of street riding. This initial section runs through some rough spots in Yonkers and includes some on-street sections. After reaching the northern neighborhoods of Yonkers, it all starts to feel European with back-to-back posh villages, mansions, and views of the Hudson. There are even some interesting stone ruins, not to mention the Lyndhurst Mansion grounds.
The trail comes and goes a bit further north and you'll find yourself on the road more than you may like, but there are some deeply wooded sections and a fun climb to a bridge over Phelps Way. There is an aqueduct museum along the way and many clear signs of former aqueduct works.
I highly recommend this trail and shall return to it many times.
Just got my new gravel bike and this trail was a perfect bridal (horse) trail ride.Mud ,cinder,dirt and gravel are what you will encounter ,but the high berms,ponds and deep woods experience are worth the trip!
I rode my bicycle from the parking lot in Goshen NY to the end of the paved trail 12 miles long. There is a dead stop at 12 miles with a fence preventing you from advancing over an old bridge.
The trail is in great or perfect condition and some new repaving was noted along the way. Walk, run, bike, rollerblade or whatever your non motorized pleasure is. I noticed a few cameras along the trail and a police officer in a golf cart.
People were all nice and offered greetings as you pass. One thing to remember is a lot of people wear earphones/buds while using the trail and may not hear your warning when you are passing.
I find railroad trails feel like they are uphill both ways, the 24 mile ride was a bit much for my first ride this year.
Great trail, my congratulations to the caretakers of this wonderful trail.
Access to the southern portion through van cortlandant park goes thru an unpaved wooded area. Basically, mud, tree roots and stones--not ideal for road cycling. Once on the south county trail, things get better but not by much. For most of the trail, you will be greeted by uneven pavement, cracked asphalt and dips (smooth pot holes).
This trail will, in time, be incorporated into the Empire State Trail.
Went for the first time yesterday. it was beautiful. Nice and wide, not over-crowded. some hills for a bit of a challenge and best part is that I was able to bring my fur baby in a safe walking environment . .
very safe plenty of hills good visibility nice and wide
I started at Watch Hill Rd near the shooting range, over the Croton Gorge, and up the road. The trail continues across the street but it’s hard to find and doesn’t look like a trail. It heads through Tea Town and is very nice for a few miles. Once you get near Rte 134 it’s a mess. Apparently it continues for another mile or two but I turned around at 134. Very nice in spots, especially when all the trees are in, say May-June.
The path is very poorly maintained, with lot of potholes and tree roots coming out. Safer to ride with that cars to be honest.
The new portion heading under the Merritt Parkway entrances (via tunnels) are installed and old train bridge over Rt 15 is now open and it's complete.
It is a continuous trail from Bridgeport (Beardsley Park) to Newtown.
Great work in completing this section.
Now we need to get Newtown on board to extend it.
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