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.
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 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 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 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...
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...
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 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 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...
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...
This is the first phase of the proposed Lehigh & Hudson River Rail Trail. The second phase will connect Hillside Park to Kittatinny Valley State Park. It is hoped that there will be an eventual...
The O&W Rail Trail follows the route of the former Ontario & Western Railroad in southern New York. In Ulster County, nearly a dozen miles of trail are available and, in Sullivan County, another 7.5...
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...
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...
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...
The Ellen Farrant Memorial Bikeway offers a paved bicycle and pedestrian route on the southwestern end of Long Island, paralleling Wantagh Parkway from Seaford to Jones Beach State Park. The trail is...
The 3.6-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...
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...
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...
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...
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...
Hudson River Greenway stretches between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes through Hudson River Park,...
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 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...
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 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...
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...
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...
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Much of New York's 15-mile 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 to Monroe. At Crane Park,...
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...
This is the first phase of the proposed Lehigh & Hudson River Rail Trail. The second phase will connect Hillside Park to Kittatinny Valley State Park. It is hoped that there will be an eventual...
The Randolph Trail system covers 16 miles of pathways through five parks, the Clyde Potts Reservoir watershed and 2,000 acres of pristine open space. The trails link schools and neighborhoods and also...
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 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 Essex–Passiac county...
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 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...
Bergen County's Saddle River County Park Bike Path traverses a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. Five park areas are linked by the multi-use...
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...
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...
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...
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...
For a dose of rural scenery, head to the northwest corner of New Jersey, where this 27-mile rail-trail cuts a nearly uninterrupted path along the banks of the Paulins Kill, a Delaware River tributary...
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...
Much of New York's 15-mile 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 to Monroe. At Crane Park,...
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...
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...
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 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 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 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 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 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 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...
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....
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
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 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 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...
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...
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...
This trail is located in the Mahlon Dickerson Reservation which is a unit of the Morris County Park Commission. The trail follows an abandoned railroad bed through hardwood forests, past ponds, swamps...
I was looking for an ATV friendly trail so my girlfriend and I could take a short ride on our new touring bike. We picked a dry but cold Saturday in November. I did my research and it appeared, based on this website, that this trail was open for ATV and/or ORV usage. We drove all the way down from Albany to find out the gates were locked on the trail and there was signage banning ATV, Horseback riding, Snowmobile usage, etc. We checked a couple of access points and it was the same thing. We were looking forward to a scenic tour of that area along the canals with the view of the mountain alongside of us. So, we wasted half a day, gas and tolls, to just basically turn around. TrailLink needs to update the trail description to include just walking, hiking and maybe bicycling. For this, I can only give the trail a 4 star rating.
Great ride, very easy, anyone can do it. It can be accomplished on a Road Bike. Surface was flat, smooth and clean.
I rode this trail a week after it opened in September 2018 because I live here. In the village of New Paltz, the east end is at the bridge over the Wallkill River with a small parklet and benches. This is very close, maybe 100 feet, to get onto the 22 mile, unpaved Wallkill Valley Rail Trail which runs from Gardiner, through New Paltz and Rosendale, to Kingston, NY. Soon to be completed is a bike lane on nearby Henry Dubois Road which will lead to a 20-something-mile fully paved trail of various names New Paltz, Highland, Poughkeepsie, Hopewell Junction. Hudson Valley Rail Trail, Walkway Over the Hudson, and Dutchess County Rail Trail. Having ridden trails all across the Northeastern states, this combined trail is in my top 3 anywhere for quality, beauty and amenities.
The River-to-Ridge is not a rail trail, it is a newly constructed gravel and dirt trail to get bikers off the main roads. There is a nice parking lot, and after you cross the road going west there is a hill and beautiful views of the Shawangunk ridge. At the west end there is access to the private lands of Mohonk Resort. Maybe (maybe not) there will be someone collect fees to ride Mohonk property. The roads also lead to Minnewaska State Park where there are many carriage roads for biking.
Parked at western end of trail in a very new parking lot on Rt 299 across from the Lowe's. Trail is beautifully paved all the way to the Walkway Over the Hudson, some of the pavement appeared to put down only days before we rode on it. State of NY is doing a fantastic job making this and the Walkway a great destination ride, installing modern bathrooms/visitor center on each side of the Walkway (open already on the west side of the river and under construction on the eastern side). On eastern side, seamlessly connects to another 13 mile rail trail. You will have to ride very slow over the Walkway, as there are a lot of walkers, but you're going to want to stop and take pictures anyway!
We enjoyed the ride through the country side and found the trail fairly empty on a early October Wednesday morning. Several parts of the trail were muddy and narrow. The best stop was the Rosendale Trestle with spectacular view. Worth riding again.
We parked at Tony Williams Park rode past the Walkway over the Hudson down to mile marked 8 on the Duchess Trail where we stopped on a bench for lunch. The path is wide and mostly smooth and only one construction area (putting in a modern restroom on southside of the Walkway). We would rate this the best trail we have ever been on as far as access, parking, restrooms (including port-a-potties in some areas) and very few rode/driveways to cross. We rode on a Thursday morning early October and the path was not crowded. Our 20 mile round trip was Fantastic!
This is a beautiful paved trail for biking, running, walking, strollers, and wheelchairs. It is well-kept and offers scenic views--from rolling fields, to bridges, to train cars, to even an old cemetery. My husband and I biked the entire length and back on a gorgeous fall day. It was a really nice ride, but be aware that it is often a false flat trail. One other major thing to be aware of is that you CANNOT access this trail from Mary Harriman Park in Harriman. Your best bet is to access if from Monroe. If heading east on the trail toward Harriman, the trail comes to a dead end fenced off bridge with no access and you're forced to turn around and go back the way you came. Hopefully someday they will fix this and extend it into Harriman for better access. That is my only complaint about this otherwise beautiful trail.
Newly paved trail is now open from the marina to Northern Blvd. This is a great ride especially during the week when it is not so crowded. As another reviewer stated one can extend their ride into nearby Fort Totten.
I love to walk the trail and have since 1971, the cross over on Whitney Ave in Trumbull is Terrifying, The cars cannot see any one passing the road way until they are in the roadway. The line of sight is completely obscured by vegetation and the small sign in the middle of the Street??? I have seen people run right across the road with out even slowing down prior to or while crossing Whitney Ave. I personally saw a woman hit the side of a car as she could not stop running in time to avoid the car. This section is an accident waiting to happen. Whitney Ave. crossing needs to be safer for both motorist and trail user.
At the end of the trail is a Kings supermarket with awesome sandwiches and more.
No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.
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