Explore the best rated trails in Ossining, NY. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and D & H Canal Linear Park. With more than 101 trails covering 729 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
It’s hard to believe that a noisy locomotive once ran through here, given that stillness is a defining characteristic of the Middlesex Greenway. Even when people pour onto the trail from the adjacent...
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 Paulinskill Valley Trail follows a creek by the same name through a section of rural New Jersey with a strong German influence. In fact, the word kill is Dutch for “riverbed or stream channel.”...
The William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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...
When complete the Green Brook Multi-Use Trail will meander for 7 miles through the communities of Plainfield and North Plainfield, New Jersey. The trail will connect major regional trails and parks as...
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...
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 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...
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 former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
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...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
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 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 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 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...
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 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 Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
_319_sc.jpg)
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 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 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 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 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 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 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 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...
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 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 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...
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...
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 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...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
This is a section of the New York, Ontario and Western (O&W) Railway line that ran across New York State from Port Jervis to Lake Ontario. The trail consists of two discrete sections: State Route 209...
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
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 corridor now home to the Sussex Branch Trail was originally the narrow-gauge, mule-drawn Sussex Mine Railroad, which opened in 1851 to haul iron ore from mines in Andover to the Morris Canal....
The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
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...
This is a section of the New York, Ontario and Western (O&W) Railway line that ran across New York State from Port Jervis to Lake Ontario. The trail consists of two discrete sections: State Route 209...
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 Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
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 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 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 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...
The Laurelton Greenway is a short but well-maintained multiuse path connecting the neighborhoods of Jamaica and Rosedale in southern Queens, NY. The two-lane paved trail starts in Jamaica, and travels...
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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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...
It’s hard to believe that a noisy locomotive once ran through here, given that stillness is a defining characteristic of the Middlesex Greenway. Even when people pour onto the trail from the adjacent...
<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...
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...
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...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
We started the trail in Middleport parking on Palmer Ave. Highly recommend this direction as it’s mainly uphill to Harriman. We clocked 19 miles exactly to Harriman. The uphill is not super intense but is uphill so the way back was super fun and easy! We stopped in Monroe on the way back to Middleport. 38 miles in total ALL PAVED and 99.5 % trail. Excellent. Little weird spot right before Goshen as the trail ends abruptly with no signs. Head into the main town of Goshen and turn right at the wine store and you’ll be back on track!
I have walked biked and jogged along greenway trails in Hauppauge along 347 from route 111 to Terry Road numerous times. Lately i run at night as do several others who i see along the trails. I have never seen the giant solar lights along the trail come on. The bus stop lights are on but the lamposts are never on and the paths are very dark I use a flashlight but others don't and it can be dangerous with debris along the pathway. I can't be the only one who as complained because it seems that since its inception they have never worked and i don't know why it took so long fpr me to complain. Concerned runner, Thank you
We started at the Hurley Marbletown Trailhead where the trail transitioned from pavement along SR 209 to all wooded. Trail is very scenic, that said trail has lots of ruts with no visual maintenance. We biked 1HR one way and turned around. Our bikes are hybrid and did not handle the poor grading very well. I would recommend wide tire bikes
I wish I could give this 4.5 stars.
It is really two separate trails with a five-mile gap. I rode both sections. The bottom section was slightly nicer and might have squeaked out 5 stars on its own.
Most of the trail is shady and scenic. the pavement is generally smooth but a few roots. However, in the northern section it is not really well-marked and a bunch of times I needed to pull out my GPS, either to guess which way to go at a fork or as the poor marking meant I went off trail. The lower section has a part in northern New Haven where it is not kept up as well and there are lots of road crossings.
We rode this trail for about 5 miles from the kilns, across the trestle, and south past farms and shaded trail. It was lovely. We quickly came upon a cave which was emitting cold air and stopped to take it in. No signage to inform you of this wonder. We brought a lunch and were disappointed to find no benches for the entire stretch. I just wanted to point these 2 things out as a way to improve the experience for others
I love this trail and the scenery. But there is a ditch with a crashed car at the bottom. The car is pretty old. Maybe late 70s or early 80s. It's between the parking space 17 park and ride lot in Monroe and the overpass. There's a green gate blocking the ditch. I would love to know more information about it if anyone knows.
Started at Milford Beach expecting a basically downhill ride. From Milford Beach to Dingmans Campground many stretches were unrideable and needed to walk bike up and down steps and steep slopes. The only positive in this stretch was that Raymondskill Falls was a short uphill walk from the trail and worth the view. By the time we got to Dingman Falls I did not have the energy left to afford another side excursion. Trail for flat sections was basically compacted cinders, the steep sections were dirt hiking trails. From Dingmans Campground to Hialeah the trails meanders up and down as well as sideways several steep cinder sections with one sign missing that almost caused a calamity. Steep drop with sharp right turn at bottom onto a bridge. Bridge was not visible until bottom and carrying to much speed right turn is not possible. Three choice run in stream, hit tree or exposed tree roots.
The trail is not recommended for street bikes and absolutely need MTB or Hybrid with suspension north of Dingmans Campground. From Hialeah to Dingmans required several side tours on to roadways, twice on Highway. Many flat stretches but also some pretty hefty grades in this run.
Historic trail with varied terrain and beautiful scenery. We parked in Rockland County and rode over the Tappan Zee Bridge and made am easy connection to the trail.
Miles of secluded, smooth, paved trail. We were there on a Tuesday and hardly met anyone. Typical rail trail views with woods and rocks, but the view of the lake and wetlands was very pleasant and broke it up. Surprised to find the white blazes of the Appalachian Trail where it crossed the bike path. Starting in Hopewell Junction heading south east there is a slight incline until Whaley Lake. Not a problem, just made it easier on the way back. After the Whaley Lake continuing south there is a slight decline which did make it a a bit of a grind on the way back but really nothing to be afraid of. We thoroughly enjoyed the day. The only reason I did not give this trail 5 stars was because of lack of and condition of bathroom facilities. When you are of a certain age this becomes more important to you :-) We did the William R. Steinhaus Dutchess Rail Trail, Walk Over the Hudson, and Hudson Valley Rail Trail the previous day, making for a nice mini-vacation. We travelled 3 hours for this trip and it was worth it.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_195571_st.jpg)
_186267_st.jpg)
_319_st.jpg)
_138996_st.jpg)
