Explore the best rated trails in Middletown, 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 70 trails covering 499 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 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 the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
The Liberty Rail Trail extends about 2.5 miles through the village of Liberty, NY, between Chestnut Street/SR 52 (near West Street) and the old rail trestle in Ferndale. The trail occupies a portion...
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 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...
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 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...
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 Columbia Trail has the distinction of being named for a natural gas pipeline that runs beneath it for 15 miles in rural northern New Jersey. The crushed-stone trail rolls along the South Branch of...
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 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 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...
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 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 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 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 rustic unpaved trail, just over three miles in length, runs along a route formerly used by the New York, Ontario, & Western Railway's Main Line through Parksville in Sullivan County, NY. 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...
Running alongside a New Jersey Transit passenger line, the Traction Line Recreation Trail has been around since 1986, when Jersey Central Power & Light donated portions of the land to the Morris...
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...
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...
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 Paulinskill Valley Trail follows a creek by the same name through a section of rural New Jersey with a strong German influence. In fact, the word kill is Dutch for “riverbed or stream channel.”...
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 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...
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 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...
This trail is much better suited to walking than to biking. It provides excellent access to the Pequest River which is stocked with trout. Not all of the bridges across the river have been decked and...
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...
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 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...
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 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...
Running alongside a New Jersey Transit passenger line, the Traction Line Recreation Trail has been around since 1986, when Jersey Central Power & Light donated portions of the land to the Morris...
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 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 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...
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...
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...
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 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 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...
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...
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 Kingston Point Rail Trail will be a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School,...
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...
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 Liberty Rail Trail extends about 2.5 miles through the village of Liberty, NY, between Chestnut Street/SR 52 (near West Street) and the old rail trestle in Ferndale. The trail occupies a portion...
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 Paulinskill Valley Trail follows a creek by the same name through a section of rural New Jersey with a strong German influence. In fact, the word kill is Dutch for “riverbed or stream channel.”...
The Wood Duck Nature Trail, appropriately named for the secretive duck, was made possible through the hard work and dedication of refuge volunteers. This beautiful trail now extends about 1.5 miles on...
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 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 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 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 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...
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 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 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...
Fun park for walks. Has fountain and ducks and paved trails for walking biking or running
Great trail for biking and just walking. So nicely maintained!
I have biked about two-thirds of this trail, and it's great. There are several access points, and many places where you can exit the trail to ride on local roads.
Ive been riding this trail since the 90s. The trail is scenic in certain sections, However, Its pretty rustic & you're gonna need at least a 1.7 tire or higher.
For those of you who have the 700c tire, A 42mm or higher will get you going. After rain fall, You will encounter lots of pockets of puddles & some mud.
Lots of wildlife & on weekends you'll bump into equestrians. If you like fishing, You'll pass a few small lakes & creeks to hang out & wet your line & have lunch.
I parked at the westernmost parking area and rode west. Nothing much to see (other than the Orange County prison) and fairly populated on a Monday.
I then rode East towards Goshen. Just before the town, a resident has put up several "No Trespassing; Private Property" signs and the trail is no more although the map shows it jagging left and coming back into town.
What you have to do is ignore the signs for about 10 yards and make a u-turn onto a road that leads up to West Main Street. Take that through town to North Church and then to St. James. You'll find the rest of the trail headed to Harriman.
The trail is excellent and well-maintained. I only went as far as Chester. That will be my starting point next time. From Goshen to Chester there were a lot of walkers and dog-walkers -- all extremely polite and practicing trail etiquette. It's a little too tame and populated for my taste, but I am guessing as you go further east, it is less so.
I will be returning.
I started in Hurleyville. Heading East, once the asphalt ended, I clearly had the wrong bike with me. It's a fat-tire trail. It was so bad that I pulled Google Maps to do a parallel side road just to see if it got any better further up. It didn't.
I went back through Hurleyville to the other end. It stops at Denman road. However, there is a gravel path that continues. Oops..after a couple of miles it just dead-ends in an industrial parking lot. I rode up to Liberty (that was pretty pointless since it was Monday and no place to eat was open). I took 52 back to Cross Farm and then down Denman back to the trail and back to Hurleyville.
I wouldn't recommend this stretch.
My wife, dog and I ride the trail nearly every day. The Hartley road entrance is a bit tricky but once you figure out how to get to in its a piece of cake. Hint...when you get into Goshen and get to the end of the first part of the trail follow the dirt path to the fence, there is a gate, be courteous and shut it behind you and ride thru the development and you will be in connect with railroad ave and see the connection for the rest of the trail. Enjoy!!!
This is a short but amazing trail on the south side of the reservoir. The word is they will be opening a longer trail on the north side. It is absolutely beautiful and, although it is only a couple of miles, it took me over an hour due to all the photo ops along the way.
You won't regret this side trip.
Beautiful in fall, but a workout going from Brewster. A few major hills.
Having not ridden this trail before we made the mistake of trying to start at the very bottom end of the trail (0.0 mi), and later in the day than normal. Even though the TrailLink map indicates that parking was 2.5mi further north, we figured we'd give it shot. Mistake. Don't do that. There truly isn't any place to park, unless you want to leave your car randomly on the side of the rode on somebody's private property. 😂
We parked up in the Gardiner lot (Main & 2nd, 2.5mi mark on the trail). We rode north from there. What a great ride. Trail is mostly shaded, covered by the tress. The leaves where changing colors. It made for a very tranquil, fall covered tunnel feeling. The was flat and well maintained. We encountered other riders, joggers, and walkers along the way. We passed through farmland, apple orchards, and small communities. The trail takes you over roads and streams.
We stopped in New Paltz for lunch. We found a bike rack near the edge of the trail and locked our bikes there. We sat outside and enjoyed a nice meal at The Parish (New Orleans fare).
We continued our ride north for another 3mi or so before we had to turn back as it was getting late and didn't want to be on the trail when the sun set. (Note - we got a very late start at the beginning of the day). The trail north of New Paltz seemed to grow less traveled, a bit more narrow. As much as we enjoyed the souther portion of our ride, it seemed to me that the norther portion was shaping up to be even prettier.
We definitely plan to ride this trail again. (I've tagged it in my Google Maps) We will plan for a longer day so that we can explore further north of New Paltz. I think I will pack lunch in a backpack so that we can stop somewhere along the trail, stream side as there where some nice pull off areas.
The trail itself is beautiful, however you take your life in your hands trying to pull in/out of Rt. 299 with your vehicle as the cyclists fly past the giant stop signs. There needs to be speed bumps or a gate to force them to stop. This is a fatality waiting to happen.
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