Explore the best rated trails in Peekskill, 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 90 trails covering 612 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 corridor now home to the Sussex Branch Trail was originally the narrow-gauge, mule-drawn Sussex Mine Railroad, which opened in 1851 to haul iron ore from mines in Andover to the Morris Canal....
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...
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 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...
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 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...
_160375_sc.jpg)
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 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...
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...
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 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 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...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
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 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 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 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...
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...
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...
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 corridor now home to the Sussex Branch Trail was originally the narrow-gauge, mule-drawn Sussex Mine Railroad, which opened in 1851 to haul iron ore from mines in Andover to the Morris Canal....
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...
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...
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 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 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 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 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 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...
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...
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...
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...
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...
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 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...
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 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...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
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 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 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 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 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 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...
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...
With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a stunner. The paved pathway begins in Olivebridge, a hamlet in southeastern New York, and spans just shy...
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 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...
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...
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...
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 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...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
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...
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...
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 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 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 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...
So glad - bit by bit this trail continues to grow.
We lived in Trumbull many years, walked, biked, ran “The Valley” and other sections, including w. Grandkids (now grown - we are GREAT Grandparents now)
So excited, last spring, to finally find safe passage through the Rt 25 interchange area.
Now live in Southside VA
ps. Anyone know about the “cow tunnels” in the Pequonnock Valley, and the tungsten mines??
We chickened out last year about half-way down and turned back because it was getting too thick with brush. Decided to take another crack at it by myself today and I found it an interesting challenge. Rocky and hilly with loose dirt and sections where parts were washed away, which made it somewhat of a challenge if youre moving at any significant speed. I ended up with a few scrapes from the sticker bushes, some of which you cant avoid because youre too busy watching the trail to make sure you dont get your wheel caught in a rut in the washed-away sections.
All in all It was a short, somewhat challenging trail, with some nice views of the river at the end. At 2 miles, it should be a nice chal;lenge for a novice or intermediate mountain bike rider, but you definitely should not try this on a road bike.
Thanks! to the HVRT for resurfacing some of the trail that the tree roots had pushed up pavement. It was nice to be able to ride without having your fillings about ready to come out Thanks HVRT
We stayed at a very nice little inn called Inn at Twaalfskill that has a driveway that connects to the western side of the bridge on the Hudson Valley Trail. The bridge is a little crowded, so you have to take care, but it is worth the spectacular view. The Hudson Valley Trail on the west side and the Dutchess Trail on the east are both well maintained and less crowded than the bridge itself. HIGHLY recommended. The Inn is a great quiet getaway that could not be more convenient for access to the trails.
The trail offers the opportunity to ride in the green and without cars for most stretches, but its views are limited.
The first part through Yonkers is very uninspiring, it looks more like a landfill than a nice trail, so I would definitely skip that part next time. Coming through those Hudson villages is nice, but it also creates the necessity to cross a lot of streets. That wouldn't have been much of a problem if the trail was designed for it, but the way it is now you need to dismount your bike because the curbs are just too high to bike over, so that definitely takes the flow out of the ride.
Signage is poor at some places as well, I would recommend a GPS unit to ride the whole trail. There are also a couple of unbikeably steep sections that also require you to dismount. The final destination, Croton dam, is impressive to see and the highlight of the route.
All in all a very mediocre biking trail, but options are very limited anyway, departing from NYC. I think I won't be riding it again.
I just cycled the new 2.2 mile Heritage Trail extension from Goshen to Hartley Road. It opened July 18 and today (July 29) I did not see a single person on this section going 4.4 miles round trip . Not one. I feel that the county spent a million dollars paving it just for me. I also cycled to other end at Harriman. This is the easiest 30 miles round trip that one can do. Kudos to Orange County for replacing eroded sections with root bumps with smooth new asphalt (lots of the Westchester rail trails sections need this improving). A review below says the trail isn’t 15 each way. It is. The Harriman to Goshen main trail ends at Saint James Place. There are no signs telling you where to pick up this new section. Common sense tells you to follow where the rail line once was. Hint: Railroad Ave. past the old train station. I had to go through an apartment or condominium complex through an open gate and there it is. Beautifully done. This just adds to the greatness that is the Heritage Trail. It is the best within 50 miles of NYC and NNJ. Dutchess Rail Trail to the Walkway Over The Hudson is the best within 100 miles. The Heritage just ends there at Hartley Road. Goshen has lots of place to eat, though, back in the town. Trailside Treats abuts it and is nice (but doesn’t open until noon).
I have ridden this trail about a dozen times over 6 years using 4 different bikes from road bike to hard tail mountain bike. I find a hard tail mountain bike with 2.5" wide tires the best match for the crushed stone.
I like how the steep hills and sharp turns break up the monotony characteristic of many rail-trails I have ridden (especially in Florida).
My latest ride was during the severe heat advisory weekend of July 21. It was very tolerable given the ample shade and cooler temperatures of the forest it mostly traverses. In the afternoon, the tree line along the fields provides good shade. Even 209 heading south is mostly shaded after 2:00 PM. I was able to bike leisurely from Bushkill to Milford and back in 8 hours with many water breaks. However, I like it best in the spring and fall when it is easier to view the river without all the undercover.
Water is available at trail-heads spaced no more than 10 miles apart, so that was no problem. Many good eateries are found in Milford but I recommend the Rooster deli at Bushkill for great hoagies and snacks. I park at the Bushkill Meeting Center next to Bushkill creek; plenty of parking with no fees.
I would rate this trail five stars except for the no bike sections between Milford and Dingman's Ferry. I really don't like biking 209 since the shoulder is very narrow with large RVs wizzing by. Also, I don't recommend biking at dusk as the trail gets difficult to navigate in the forest at low light.
Started at the Milford Beach parking on Sunday July 21st. Didn't see anyone on the trail. Enjoyed the scenery. This is definitely a trail for a mountain bike. I should have done my homework - there's a section of the trail between Pittman Orchard and Conashaugh and another section between Conashaugh and White Pines that are for hiking only and closed to bike riding. You will need to ride on US 209. I will come back to the trail at another time to ride other trail sections. JC Capote
Just today rode up to West end of trail. Well maintained. Yes mile markers would be great to have. Crossing main highway was very safe due to walk light set up Thanks for a great safe ride
My son and I traveled from Kingston NY. We went to Harriman to start but there is NO access to the trail from Mary Harriman Park. If you ride out of the park and down the road you can not access the trail because it is blocked off due to a broken bridge and is all grown over in weeds and over growth. We got in our car and went to the beginning of the trail in Goshen where there is a parking lot and the official start of the trail. The trail is great! You take the trail 12.30 (give or take) miles to where a huge fence says "TRAIL ENDS HERE." Therefore this is not a 15 mile trail. It is just over 12 miles one way and over 24 miles round trip. Minus the misinformation at the Harriman end, this was a great trail and I would definitely go back again. It is completely paved!
Heading north from Diddell road is a breeze. Got to the Walkway and were rewarded with a great view and friendly folks! Returning southbound is a little tougher since there is the slight upward grade. Get ice cream or a slice at the frozen caboose!
Get Your 2018 RTC TrailNation Jersey!
Download the TrailLink mobile app and take TrailLink with you!
Donate and Get a FREE 2018 RTC Guidebook!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_164090_st.jpg)
_160375_st.jpg)
_319_st.jpg)
_138996_st.jpg)
