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 74 trails covering 537 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 Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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 Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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 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...
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 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 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 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 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.”...
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...
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 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...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
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,...
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 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...
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...
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...
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...
In the mid 1800s Chester, New Jersey, was the home of the iron ore industry; railroads shipped the ore all over the county. With the end of the industry, however, the rail lines were abandoned, turned...
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...
This 5.5-mile trail is the rail-trail section of two much longer trails, the Long Path and the Shawangunk Ridge Trail, that converge and share the same path for part of their respective routes. Built...
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 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 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 William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.1-mile trail runs through what seems...
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 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 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 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...
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 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...
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...
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...
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...
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...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
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 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 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 Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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 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...
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 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 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 Delaware & Hudson Canal Linear Park is 45 acres with a trail situated along the historic D&H Canal. Remains of the original locks, dry dock and waste weirs are visible from the towpath trail....
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...
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 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 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 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...
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...
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...
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...
The Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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 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...
Part of a series of trails - Horseshoe Lake in Succasunna, Black River Wildlife and Patriots Path - we started at Horseshoe Lake and went to the end at Chatham, an in and back trail, and it was a bit over 13 miles. Trail is ok, a bit bumpy in places, but not dangerous. Very flat, shaded and flanked by wetlands. We didn’t have a problem with insects, but can see where it may be a problem in wetter weather. Although beautiful through the woods, it got a bit boring by the end. We finished by doing the trail around Horseshoe Lake and it was wonderful. The lake path is well used, and it was nice to see families about enjoying the outarea. Parking is plentiful if you begin at the lake.
Beautiful, shady, wide and well maintained trail. Loved the falls and reservoir just off the trail, the Clydesdale farm and the easy ride.
I rode south then east from rt. 8 in Poughquag. There is a small missing section above the Croton River east branch in Brewster . You can walk your bike along RR, via open fence for this 50 yards or so or cycle downhill on Peaceable Hill rd and up the hill on East Main to get back on. The TrailLink map (as of 8/3/22) shows the trail ending here. But it continues a few miles east into Connecticut. About a half mile over the line to an overpass at Mill Plain Rd in Ridgefield CT. Smooth all the way with terrific scenery. Many lakes.
Beautiful ride from north of Van Cortlandt part to Mahopac.Well paved and maintained.Connected to the North County trail And the Putnam trailway
I never met a rail trail I didn’t like until today. Challenging hills is an understatement for those of us seniors used to railroad grade only.
Not a portapotty for the 7 miles north at the trailhead. Check that trail off our list.
Trees down, gate closed near trail end!NEEDS Mowing! Staff seems indifferent.
Excellent trail, nice for a walk, run or bike. Beautiful area, pleasant folks. Good for families but watch out for serious cyclists when you have small riders.
Technically not for bicycles. But you still can ride if you want. On a weekend day I saw only 3 people went on a walk. Keep in mind that your bike might be dusty after the ride since there is no regular asphalt.
I did 2 rides on McDade with my RAD City 3 Ebike. First ride started at the Bushkill access. This was a nice ride, but the surface is large stone/gravel. Not a smooth ride, but the scenery was nice. The next day, we accessed from the Eshbach point. This was WAY out of my comfort zone. Very steep mountainous terrain. The surface was much smoother here, but the inclines were so steep. We had been told that Eshbach was “the nicer ride”. My bruises say otherwise! Rider be warned!
My husband and I were visiting family in the area and needed to get in our weekly long runs. We started on the Old Putnam trail and then connected to the South County. The trail was somewhat narrow for dual direction bike and pedestrian traffic but was in good condition It does offer mileage markers and periodic maps. It connects to a number of other trails. And it has minimal intersections in the portions we used. It did not seem to be a practice of the bikers to announce themselves with and ‘on your left’ as is common on our home trail so beware of fast moving bikes.
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