Find the top rated bike trails in Sleepy Hollow, 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 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...
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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...
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 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...
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 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 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...
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...
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....
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...
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 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 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 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 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...
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...
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 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 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 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,...
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...
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
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...
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 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 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...
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 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...
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...
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 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 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...
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 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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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....
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...
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 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...
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...
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 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 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 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 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...
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 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 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 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 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...
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
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 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...
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 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 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 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...
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...
Wednesday afternoon September 16, 2020
Weather: Glorious mid 70's and dry
I usually ride trails, but this linear park was just wonderful. VERY scenic for an urban park with the Saddle River (a stream really) and several large ponds, lots of forest. I even saw several deer and wild birds. Off the nice asphalt there as some dirt single-track for the more adventurous bikers. Lots of nice parking, bathrooms and other amenities. This is the best urban biking I have ever done. When I was done riding ever part of the path, back and forth, my Strava said 18+ miles. Thanks New Jersey.
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.
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.
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
Awesome, peaceful, beautiful surroundings. Loved the break of trails they town on road then back in the woods. Tree farms.
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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