Explore the best rated trails in Hauppauge, NY. Whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail. With more than 60 trails covering 376 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.
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 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 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 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 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 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...
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 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...
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 Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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 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...
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,...
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 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 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 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...
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 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 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 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 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 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...
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...
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 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 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 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 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...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 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...
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...
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 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 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 Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
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 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 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...
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...
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...
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...
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
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...
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 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 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...
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,...
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 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 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...
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 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 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...
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 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 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...
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...
I did the southern part of the trail from Massapequa park to Bethpage park. While the scenery and lakes are nice, the trail needs repair. There are many cracks and bumps especially near the beginning of trail. Also there are several road crossings but cars were careful to yield to cyclists.
This trail is great for biking but there are a lot of people who use it for walking.
It is perfect for quick morning ride with nice view.
My friend and I rode from Millwood on the North County Trail and just kept going. We ended up on the Putnam Trailway for a total of 46 miles. There are several decent hills on this segment of the trail. There are some street crossings but they are not very busy roads. You eventually come to the end of the trail, which is clearly marked. Near the end of the trail is a large reservoir. The trail is completely paved with just a few bumpy spots. We rode on 10/10 and the foliage has not changed much yet.
Level easy trail quiet and very pretty. Tricky entrance and exit onto busy road. Short easy trail. Wear boots muddy areas.
We started at Tait road entrance around 4:30 pm. Path was leafy but dry and good with great views.
Great trail. We took the fork to piermont and went over the TZ bridge. Awesome ride
The southern half of the trail is great - smooth, not too steep, and mostly shaded. The northern half, until you reach the North County Trail, is terrible. Cracked, potholes, and sunken spots that are hard to see for almost the entirety of the trail.
I am an experienced cyclist who doesn't mind hills and other challenges. My wife is a casual rider who likes mostly flat, but not boringly flat, rides.
I drove almost an hour to scout out this trail for one of the leisurely rides we like to do together. After literally two minutes, I turned around and rode back to my car.
This trail is NOT suitable for occasional cyclists, beginners, older riders, or younger riders. In fact, I don't really know WHO it is good for, as for someone like me who can live with a few hills, it is way too short.
Perhaps if it, at least, led somewhere scenic or lined with coffee and pie shops, it might be worth the effort. However, it appears to start in the middle of nowhere and end in the middle of nowhere.
I gave it two stars instead of one on the chance that it might get better after the first thousand feet I covered. You'll have to find out for yourself. I'm not going back.
We did this trail plus the connector trail to Rockland Lake. Really fun! A few steep hills where got off to walk, lots of scenic views of the cliffs & the river, some old ruins the kids enjoyed checking out. The leaves are just starting to change (late Sept).
We rode from Sleepy Hollow High School to the Croton Dam and back on 9 26 20, total 22 miles round trip.
This is quite a varied trail experience. First, there are several on-road segments that connect the trail sections. The trail itself was mostly hard packed dirt, with some gravel...you need a trail bike or a mountain bike. Basically flat, but some of the road crossings had ups and downs and there were a few slightly hilly areas too.
It’s a complicated route, you definitely need a map or a Ride With GPS route or something similar….trail has signs but not always marked clearly. Old Croton Aqueduct.org has a lot of info.
The first section, from Sleepy Hollow High School to Scarborough was all off road. Once in Scarborough, we took a detour down River Road, to Creighton, to Scarborough Station Road to avoid a section right along Route 9. Crossing Route 9 at Scarborough Road, you ride on-road up a small hill to Long Hill Street, where you pick the trail up again. This section ends in the parking lot of an apartment building You’ll need to cross Route 9 and make your way diagonally through Nelson Park and Nelson Sitting Park to Spring Street in Ossining. After a couple of blocks we took a right on Maple Street and then on the left you’ll see the trail proceed between buildings…sort of like a walkway. This “walkway” continues through Ossining, over a nice high bridge and eventually ends up out by the Northside fire house, where you pick up the trail again. The next big cue will be crossing Route 9 again at Audubon Street, you ride on road up to Piping Rock, take a left, and pick up the trail shortly on the right, finally coming out on Ogden drive. Turn left, ride on road to Old Albany Post Road, turn right, pass under the highway, and then you have the choice of turning right on Shady Lane Farm Road and picking up the trail to go around the GE property (this was very rough, hilly, and difficult) or staying on road, riding uphill and turning right on Hillcrest Road. Both options take you out to Indian Brook Service Road, where you’ll again pick up the trail and follow it to the Croton Dam, passing over Quaker Ridge Street a number of times.
The area through Rockefeller Park and Scarborough is really nice, including that off road detour in Scarborough where you can see the river behind some nice houses. The section next to Rockefeller park is really beautiful, you can see the hiking trails of the park from the Aqueduct. And the section immediately before you reach the dam is nice too, pretty wide, nice tree-lined stretch. I have to say though that the section to get to that (around the GE offices) is rough. And you have to ride through downtown Ossining, not hard but not of course a real trail, and there’s one section where you have to walk your bike up and over some steps. So, all in all – sort of a mixed review, some really nice sections and views but be aware that there are some challenging sections and on road sections too. And please note that there’s a whole other section south of here that goes all the way to NYC.
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