Find the top rated trails in Sleepy Hollow, 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.
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Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
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 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...
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 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"...
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 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...
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 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 Wallkill Valley Rail Trail extends more than 20 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
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...
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
NOTE: A section of trail from Popamora Point to the Atlantic Highlands Marina has been reopened after storm damage, but the trail is primitive in this section and there may be icy, wet, or muddy...
The Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
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 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 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 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 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...
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
This trail is in an area rich in geological history. Zinc and Iron Ores were transported along this branch from mines in the area that operated for over 200 years. The trail is scenic with a slight...
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 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 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 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...
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
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...
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 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 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...
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 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...
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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...
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...
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...
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...
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 2.8-mile eastern phase of the Bedminster Hike and Bikeway allows pedestrians and cyclists to safely traverse part of Bedminster Township by crossing over I-287 and US 206/202 via a series of three...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
The Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
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 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...
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 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 Wallkill Valley Rail Trail extends more than 20 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster...
Located in the mid-Hudson Valley is a remarkable trail that is picturesque and family friendly. This flat, paved Hudson Valley Trail stretches nearly 4 miles through hardwood forests, over Black Creek...
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 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 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...
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...
<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...
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 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...
Hudson River Greenway provides a continuous 11-mile route between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes...
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...
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 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...
We started in High Bridge NJ..Trail has a slight incline in both directions,but nothing to speak of..At first you ride high above the river..nice views.Just watch where you're going you don't want to ride off the side.There is a lot to see,different scenery along the way,waterfalls ,woods,river,residential..bridges..We seen a few deer.Mostly shaded.most of trail is wide,as we kept riding further ,some parts were a little narrower.but not bad.It started getting little muddy,had been raining so we ended up turning around the 11th mile & rode back(22 miles total) We noticed that towards the end,the trail wasn't kept up as well & didn't see any mile markers. But still nice. Not really any bathrooms,probably can go into one of the towns. Was a porter potty in parking lot. Would like to go back & start in other direction.
Thursday, August 09, 2018, 90'F and humid
Yeah, a good ride, which connects via tunnels under the highway to Jones Beach and a more direct connection to the 5-mile bike path that goes north to the mainland. Get sweaty then enjoy the salty ocean beach waters. A go
The storms in NJ on August 16th caused severed damage to the trail. The pathway has precarious ditches now and much of the path is no longer ride-able via bike. I truly hope they fix it soon as it really is a great trail.
This was our first time here, and thankfully it was not too crowded. The foliage cover and the path are incredible, though, so you can enjoy a lot of streams and greenery while walking/jogging/bicycling. For cycling, it’s pretty mild, so if you’re looking for a challenge, this might not be for you. Wonderful family bike morning!
Speeding and unruly bikers come often. Many forgo the bikers' decorum of announcing their approach from behind. " On your left " or "On your right " should be the case, but that is actually the exception. Just be careful if you are walking. It is the only fly in this ointment. The section from Dunkerhook Road in Paramus to the northern end in Ridgewood pleases the sense much.
Great ride but especially by IBM and where there is an active rusty river flowing there needs to be work done.
Extremely steep in some sections (not bike-able), maybe 10% is paved, mostly construction type gravel. Was stuck in the very lowest 3 gears for most of the ride. Did not come across any other bike rider. Not a pleasant ride by any stretch of the imagination. Quite a few hikers though.
We were driving home to PA from CT and stopped to stretch our legs on this trail, so we didn't ride the full length. We started at Goshen and there was plenty of parking in the municipal lot that sits right at the trail head; this was a Monday afternoon, but there was still plenty of parking (thank you to the town for providing free parking!).
The trail is nicely paved and very well maintained. The first two miles were a bit noisy because the trail runs parallel to a busy highway, but after that it was quiet and relaxing. We went a bit beyond Chester and turned around. (Unlike some other reviewers, we didn't find Chester particularly charming.) The trail was flat, easy, well shaded, and relaxing, and we were grateful to the people who keep it in such good condition. Our only (VERY minor) complaint was that close to Goshen the trail sometimes had the feel of riding moguls, probably because tree roots are growing beneath the asphalt. Overall, we would recommend the trail.
After riding, we left our car in the municipal lot and walked two blocks to the Sunshine Cafe. Although the signage made us think it was just a juice bar, it had a nice menu--great paninis and a long list of specialty burgers. We recommend the restaurant highly.
Absolutely love this trail. First off, get there early. Sandy Hook is a popular place and after 9 on the weekends there will be a wait at the entrance to get in.
You can park anywhere and jump on the trail. It's paved and a smooth ride. The view is great and changes from water to trees and back. There aren't really any hills to worry about so it's mostly easy pedaling.
I usually rig a chair to the bike and stop off on the bay side to relax for bit.
This is a beautiful trail. I always start at High Bridge and work my way towards Long Valley. There is a slight incline in this direction. It makes for a much easier ride coming back.
This trail is well maintained and easy to ride along the entire length. There are parking areas along the route so you don't have to ride the whole thing. It is very scenic and there are many photo ops. You will not be alone on the trail but it isn't over crowded either.
I've seen all types of bikes on here; fat tires, road bikes, hybrids, MTBs. The trail is smooth enough that any will work fine. This trail is multi-use and there will be people walking and even some on horseback (past Califon).
I completed this trail this weekend. I started at the entrance of Beardsley Park and ended at Swamp Road in Botsford. The trail is beautiful and very quite. I highly recommend this trail. I would suggest stopping at Pepper Street as a portion of the trail between Pepper Street and Swamp Road is not really a trail. The "trail" is very narrow and overgrown ( I rode through this area with my arms pressed to my sides and still could not avoid the trees/leaves brushing against me). Also, the area has a very high concentration of mosquitos. All in all the trail is AWESOME and I will be riding it (up to Pepper Street) once a week.
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