Find the top rated bike trails in Ossining, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
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 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 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...
The Fort Washington Park Greenway brings residents and visitors to Washington Heights right up to the edge of the Hudson. The mile-long trail begins near the pier at the end of Dyckman Street and...
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...
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 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...
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...
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 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 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 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 old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
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...
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 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 O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
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 O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
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 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...
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...
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
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 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...
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 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 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...
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...
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Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
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 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 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...
Running alongside a New Jersey Transit passenger line, the Traction Line Recreation Trail has been around since 1986, when Jersey Central Power & Light donated portions of the land to the Morris...
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...
The Sandy Hook Multi-Use Pathway travels 8.7 miles alongside the picturesque beaches and historical monuments of the Sandy Hook peninsula. The pathway begins in the Gateway National Recreation Area...
The paved pathway running through West Hudson Park offers a scenic, tree-lined escape between Harrison and Kearny, NJ. 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...
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...
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 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 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...
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 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 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...
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...
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...
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 Joseph M. McDade Recreational Trail runs nearly the length of the Delaware Water Gap National Recreation Area on the Pennsylvania side of the Delaware River across from New Jersey. The protected...
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 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...
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 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 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 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 two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
My wife and I love to walk in scenic outdoor areas. This level path is perfect. Enough length to get exercise without overdoing it. Easy access from both ends. Parking is limited at Mulford Rd but there is a paved parking lot at the Lake Iliff Rd trailhead.
Many varieties. Through woods, paved paths. Convenient if you need to pick up something from any of the hundreds of stores around
Pros: - Perfect for everyone at every age. Flat terrain. 3 mile walk, 6 miles round trip. - Water pictures, trail pictures, field pictures. - Well shaded Cons: None!!! Unless your seeking a challenging long trail. - For mountain bikes only maybe hybrids Thoughts:
Great trail with greens and manageable hills. But some dangerous crossings and noise highways. Recommend ear buds. I wouldn’t take my kids for whole trail. Just south is fine. Will definitely go during foliage season.
I've logged about 20k miles of road biking across the United States namely in WA, MO, OH, PA, MD and FL, and maybe 10% of that on trails. To get to stay 99% of the time on a car-free trail for almost 50 miles (as a loop) is rare- and to have some scenery- is nearly unheard of. Thrilled to be in CT now and using this as my go-to ride.
Rode from the trail parking lot in Andover to Lafayette. IPhone said 8 miles each way. My husband rode a commuter bike which did fine on this stretch. We saw two bow hunters from the trail - we had not realized that deer season had just started - and were happy we had worn vivid colored shirts, albeit to be visible to cars. We stopped for brunch at the Millside cafe in Lafayette, which is visible from the trail. I recommend it as a tasty destination!
We rode this trail on 9/12/20, starting at the parking lot on route 63.
Overall, a nice trail, but it has a lot of plusses but also some things that could be considered “minuses” by some.
Plus:
Shaded, pretty sections high over the adjoining forest.
Some nice scenery including horse farms (and horses share the trail, we passed several), plus several ponds. Route goes through the woods the whole way…very little in the way of passes through suburbia.
Not crowded.
Not a huge number of road crossings, and typically with good sight lines.
No big hills, some gradual ups and downs.
Minuses:
Most of the train is hard packed dirt or stone dust that makes for a good surface. However, there are significant sections that are a bit rougher. Some of the road crossings involve a downhill, cross the road, and then an uphill…often with a lot of stone or sand involved. There is a section around mile 8-9(when going West) where the trail follows something like a creek bed, with large stones that make it problematic (we walked this section). There are some embedded stones along the way so you have to watch where you’re going and steer around them..or even walk briefly. Some sections do have some drainage issues, so just need to be careful there. And parts of the trail become more like singletrack. We were able to navigate the entire route with our mountain/trail bikes (30 or 32 cc tires)…I would not recommend a conventional skinny tire road bike here.
Please don’t think the minuses outnumber the plusses here. Overall I recommend this trail because it’s pretty and ridable. Maps are available at the Connecticut DEP website.
Finally I recommend starting at the Naugatuck route 63 parking area…several other posters have noted that there’s basically no parking if you start in Southbury.
Check out the Air Line trail and the Hop River trail, not too far away in central Connecticut, for other options you may want to try.
There is nothing interesting to explore here IMO. Btw there is no shade so it’s extremely hot in summers.
This is a nice ride as it takes you thru some wooded areas then you drive along Richmond Ave for a good part. You can continue along a very narrow path on Arthur Kill Rd to get into Bloomfield park and continue your ride in there as well.
My review is more conservative. This bike trail is mostly in the woods where you don’t get sunburn. There is also a an asphalt /gravel path for your choice. It’s worth a normal weekend visit but not a special tour to it
Rode this trail from Rockwell Lane to the Trestle and back Sept. 3 --- the trail was muddy with extensive puddles that were too deep and wide to ride through. As a result we had to do a lot of careful walking the bikes around the puddles in order not to fall in the mud. Riding was made even more treacherous by the heavy and numerous branches that covered the trail and frequently got caught in the spokes stopping the bike and pulling it down! This was a miserable experience. I understand that the branches were left by maintenance crews cutting brush on the sides of the trail, but one would have thought they would clear the cuttings from the trail bed for the cyclists! The part of the trail after the cement works to the trestle was much clearer and less muddy. I think its a shame that the crews did not clear trail of branches. I have never seen a rail trail in such bad condition!
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