Find the top rated trails in Ossining, 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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Sandwiched between the Hudson River and the Catskill Mountains near the busy US Route 209 corridor, this trail has a little something for everyone. The Delaware & Hudson Canal Heritage Corridor (D & H...
The City of Port Jervis is the latest community to save a portion of the former D&H Canal and turn it into a greenway for use by residents and visitors. A section of the canal, which is approximately...
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 New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
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 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 Bashakill Wildlife Management Area is located on the Orange County-Sullivan County border just south of Wurtsboro, New York. It consists of over 3,000 acres of wetlands and uplands which were...
The Joseph M. McDade Recreational Trail is named after a former member of Congress from the area known for his dedication to public lands. The trail, located within the Delaware Water Gap National...
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...
In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...
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...
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,...
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 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...
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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 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 3.5-mile Middlesex Greenway connects the towns of Edison, Metuchen, and Woodbridge in northeastern New Jersey. The paved pathway, which follows the route of the former Lehigh Valley Railroad...
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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 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 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....
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...
This trail goes through the Black River Wildlife Management area along streambeds and forest. Equestrians must have a NJ Wildlife Permit, which is available from NJ DEP for a fee. The trail follows...
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...
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 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...
In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...
Sandwiched between the Hudson River and the Catskill Mountains near the busy US Route 209 corridor, this trail has a little something for everyone. The Delaware & Hudson Canal Heritage Corridor (D & H...
The multi-use pathway spanning the length of New Jersey's Sandy Hook peninsula offers beautiful views of the ocean, as well as shady sections through maritime forest. A bird observatory and wildlife...
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 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...
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...
In June 1986, the Morris County Park Commission dedicated this recreation trail that runs parallel to the New Jersey Transit Line railroad tracks. The path utilizes a little over three miles of...
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 Sussex Branch Trail got its start in the late 1840s as the narrow-gauge, mule-drawn Sussex Mine Railroad, whose primary purpose was hauling iron ore from the mines in Andover to Waterloo Village...
The Berkshire Valley Management Area Trail passes through hardwood forests and affords views of the valley below to the right. Equestrians must have a NJ Wildlife Permit, which is available from NJ...
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 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 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 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 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...
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...
This 2.1-mile long paved path runs directly adjacent to (about 30-40 feet off of) the Boulevard in Mountain Lakes, NJ, and follows the exact route of a former trolley line operated by the Morris...
<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...
This trail goes through the Black River Wildlife Management area along streambeds and forest. Equestrians must have a NJ Wildlife Permit, which is available from NJ DEP for a fee. The trail follows...
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 system of trails in Loantaka Brook Reservation are open to hikers, cyclists and equestrians, although the trails are marked as to which uses are permitted on each segment. Loantaka Brook...
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A short rail trail with two covered bridges occupying a portion of the former Mount Hope Mineral Railroad right-of-way in Wharton, NJ. In the future this trail will be linked with the Rockaway...
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 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...
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 New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
The D & H Canal towpath is nestled within the 300-acre D & H Canal Park in the New York hamlet of Cuddebackville. The crushed-stone trail, stretching just over a half mile, is one section of a larger...
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 D&H Canal Linear Park is 45 acres with a trail situated along the historic D&H Canal. Remains of the original locks, dry dock and waste weirs are visible from the towpath trail. Interpretive signs...
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 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 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 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 Sussex Branch Trail got its start in the late 1840s as the narrow-gauge, mule-drawn Sussex Mine Railroad, whose primary purpose was hauling iron ore from the mines in Andover to Waterloo Village...
A little difficult to get to but was worth it. Great route for all levels
All asphalt no real hills, places to eat behind the golf driving range and at the end of the Trail in Goshen. Also the first historic trotters horse track.
Wide lightly trafficked rail trail that is great for a walk, easy hike, trail run or easy mountain bike ride. While the trail is wide, in some parts it is merely a footpath in the grass. Part of a loop that spans over 13 miles. Bug spray is recommended.
On foot, at even a moderately fast pace, I was besieged by no-see-ums the entirety of the trail. Stagnant water abounds next to this trail so this is not surprising. They were attacking my face like something out of a Game of Thrones battle. (I think I saw one riding a tiny tiny dragon the size of a mosquito - or maybe they had just driven me stark raving mad by that point.) The only way to be free of them was to wave my hands in front of my face or run faster than they could keep up with me. I saw no one else on foot but saw several bicyclists. I think either running or bicycling is definitely the way to go on this trail.
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.
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.
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