Explore the best rated trails in Sleepy Hollow, 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 102 trails covering 643 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.
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 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 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 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...
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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...
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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...
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 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 Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...
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...
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 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...
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...
This bike-ped path in Roselle Park, Union County. The bike path is nestled at the bottom of the railroad embankment carrying New Jersey Transit's Raritan Valley Line. Stretching between Galloping Hill...
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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 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 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 Perth Amboy Harbor Walk offers scenic views of the Raritan Bay and Raritan River as it hugs the shoreline of the City of Perth Amboy, founded in 1683 and home to one of the nation's oldest ports....
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 Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...
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 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...
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 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 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 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 Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
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...
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 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...
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...
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 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...
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 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...
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...
The Great Valley Trail, built on the former Lehigh & New England Railroad, offers an unpaved, natural experience through quiet woodlands between the townships of Hampton and Frankford. Although...
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...
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
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...
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 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...
<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...
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 bike-ped path in Roselle Park, Union County. The bike path is nestled at the bottom of the railroad embankment carrying New Jersey Transit's Raritan Valley Line. Stretching between Galloping Hill...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
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...
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 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 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...
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...
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...
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...
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 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 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...
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...
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
Some say the Delaware River Trail is the best in NJ. My vote is for Columbia Trail. The only negative is that it is a bit short at 15 miles. The trail is usually wide and well maintained, I've never seen it crowded, but I'm retired and use it during the week. The canopy of trees keeps it cool in the hot summer days of July and August and the turning leaves are spectacular in the fall. About 12 miles from High Bridge, in the town of Long Valley, is a great little coffee shop, the Coffee Potter, that sells pastries and really good coffee and teas. If that isn't enough, less than half a mile from the trail at the same intersection, you can ride to a group of three restaurants, a brew pub, a Latin restaurant, and and All American Cuisine restaurant. Beginning at High Bridge there is some minor elevation. I suggest starting there, so that coming back is easier.
Most of the trail is crushed stone, but there are sections of really hard dirt and some short stretches that might better be described as gravel, as well as a paved section - also very short. There are a few places intersections where a cyclist has to cross a road, but they aren't very busy. Still, caution is always recommended. I've ridden it with no problem with both a hybrid and a gravel bike, and that's what most riders use, but I've seen road bikes navigate the trail with no difficulties. A mountain bike would be fine, but isn't necessary.
Although this is an easy ride, if you're miles from your car and have a breakdown, it's still a problem. Bring the usual necessities in case of flat or other fixable breakdowns because of that distance. Watch for deer and other wildlife. I understand there are black bears, but I've never seen one. Bring the family. Enjoy.
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.
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.
Found a 20-mile gem on the TrailLink app. Great ride until you hit the 6 1/2 mile mark to the 8-mile mark. It’s all mud and horseshit, but I was able to get through it. The first 6 miles are great for the family after that; advance riders only
I have done the trail four times so far, and it is a great experience. I usually take route 25 up to Monroe, hang a right off of 25 to the park, and park my car there. The last leg of the north end takes you to an abandoned factory, and it’s a little sketchy. I don’t recommend it. But if you take the south route all the way down to Trumbull round-trip at 15 miles it is beautiful. The paths are extensive, and as a bicyclist, you could call out to everyone if you were on their left or right. It’s a very safe and fun trail for the whole family.
Some really beautiful areas. But not suited to road bikes!
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