Smallwood, NY Bike Trails and Maps

817 Reviews

Looking for the best Bike trails around Smallwood?

Find the top rated bike trails in Smallwood, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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32 Results
Activities
Length
Surfaces
Type

Ashokan Rail Trail

11.5 mi
State: NY
Crushed Stone

Ashokan Reservoir Promenade

2.7 mi
State: NY
Asphalt

D & H Canal Towpath

0.4 mi
State: NY
Crushed Stone

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Lake Iliff Trail

1.1 mi
State: NJ
Ballast, Cinder, Crushed Stone

Parksville Rail Trail

1.3 mi
State: NY
Cinder

Sussex Branch Trail

21.2 mi
State: NJ
Cinder, Dirt, Grass

Trolley Trail (Lehigh Valley)

4.7 mi
State: PA
Boardwalk, Crushed Stone, Dirt, Grass

Walden-Wallkill Rail Trail

4.3 mi
State: NY
Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel

Walkway Over The Hudson

1.6 mi
State: NY
Concrete

Wallkill Valley Rail Trail

21.4 mi
State: NY
Asphalt, Cinder, Dirt, Gravel

D & H Canal Trail - Bashakill Wildlife Management Area

5.7 mi
State: NY
Ballast, Cinder, Dirt, Grass

D&H Rail Trail

39 mi
State: PA
Ballast, Cinder, Crushed Stone, Dirt

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

Lackawanna River Heritage Trail

17.9 mi
State: PA
Asphalt, Crushed Stone

O&W Rail Trail (Ulster County)

18 mi
State: NY
Asphalt, Cinder, Crushed Stone, Dirt, Grass

Paulinskill Valley Trail

27 mi
State: NJ
Ballast, Cinder, Crushed Stone, Dirt, Grass
Accordion

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

Liberty Rail Trail

2.4 mi
State: NY
Asphalt, Cinder, Dirt, Grass, Gravel

O&W Trail (PA)

32 mi
State: PA
Dirt, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Karamac Trail

1.5 mi
State: NJ
Cinder, Dirt

Hudson River Brickyard Trail

1.5 mi
State: NY
Asphalt, Woodchips

Klara Sauer Trail

1 mi
State: NY
Crushed Stone

Marcus J. Molinaro Northside Line

0.57 mi
State: NY
Asphalt

Midtown Linear Park

0.9 mi
State: NY
Asphalt
Trail Image Trail Name States Length Surface Rating
The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The trail sits on...
NY 11.5 mi Crushed Stone
With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a paved pathway that spans just shy of 3 miles along the reservoir's southern shoreline. About the...
NY 2.7 mi Asphalt
Although the D & H Canal Towpath is a short pathway (about 1 mile roundtrip), it offers scenic views of the Delaware and Hudson Canal and the Delaware River in Minisink Ford, New York. You’ll see the...
NY 0.4 mi Crushed Stone
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...
NY 19.4 mi Asphalt, Crushed Stone, Dirt
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
NY 7.1 mi Asphalt
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...
NJ 1.1 mi Ballast, Cinder, Crushed Stone
The Parksville Rail Trail is the northernmost section of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port...
NY 1.3 mi Cinder
The Sussex Branch Trail is a 21.2-mile trail that runs between Branchville and Byram in northern New Jersey. Following a former railroad corridor, the surface of the unpaved trail is a mix of dirt,...
NJ 21.2 mi Cinder, Dirt, Grass
For family riding and walking, the Tannersville Bike Path offers a 2-mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
NY 2 mi Dirt, Gravel
The Trolley Trail uses a former interurban line to link several communities north of Scranton. The trail comprises two disconnected sections that total 4.7 miles, although the nonprofit Countryside...
PA 4.7 mi Boardwalk, Crushed Stone, Dirt, Grass
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...
NY 4.3 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
NY 1.6 mi Concrete
The Wallkill Valley Rail Trail runs 21.4 miles between Kingston and Gardiner through woods, fields, farmland. About the Route The corridor’s current incarnation as a linear park welcomes all...
NY 21.4 mi Asphalt, Cinder, Dirt, Gravel
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 13.8-mile trail runs through what seems...
NY 13.8 mi Asphalt
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...
NY 5.7 mi Ballast, Cinder, Dirt, Grass
In the forested and farm-dotted hills of Pennsylvania’s northeastern corner, the D&H trail runs 39 miles between the small town of Simpson and the state’s northern border. The crown jewel of the...
PA 39 mi Ballast, Cinder, Crushed Stone, Dirt
The Kingston Point Rail Trail is a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School, City...
NY 2.15 mi Asphalt
The multi-use Lackawanna River Heritage Trail (LRHT) follows Pennsylvania's Lackawanna River and, when complete, will be more than 70 miles. The trail begins at the confluence of the Lackawanna and...
PA 17.9 mi Asphalt, Crushed Stone
The O&W Rail Trail follows the route of the old NY O&W Railroad (Kingston-Port Jervis Branch) right-of-way for 19.1 miles through Ulster County, NY, between Kingston and Ellenville. The O&W Rail...
NY 18 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
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.”...
NJ 27 mi Ballast, Cinder, Crushed Stone, Dirt, Grass
Accordion
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...
NY 4.9 mi Gravel
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...
NY 1 mi Cinder, Gravel
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...
NY 0.6 mi Crushed Stone
The Liberty Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 2.4 mi Asphalt, Cinder, Dirt, Grass, Gravel
The O&W Trail (PA) stretches 32 miles throughout northeastern Pennsylvania. About the Route There are two trails named the O&W: one in New York and this one in Pennsylvania. Although the...
PA 32 mi Dirt, Gravel
The Sullivan O&W Trail runs for 20.65 miles in Sullivan County in 7 distinct sections along the NY O&W Railroad Main Line and Port Jervis-Kingston Branch rights-of-way. The Sullivan O&W Rail Trail...
NY 20.65 mi Asphalt, Grass, Gravel
The Karamac Trail is a short walking trail that starts under the Interstate 80 bridge on the New Jersey side of the Delaware River. The trail follows an old railroad right-of-way; there is a railroad...
NJ 1.5 mi Cinder, Dirt
The Basha Kill Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 5.5 mi Dirt, Grass
The Hudson River Brickyard Trail runs 1.5 miles from North Street to John Street in East Kingston. Located in Sojourner Truth State Park, the trail follows the shoreline and offers scenic views of...
NY 1.5 mi Asphalt, Woodchips
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...
NY 1 mi Crushed Stone
The Marcus J. Molinaro Northside Line is a 0.57 mile dual-track trail that connects trail users between the city and town of Poughkeepsie. While the northern end of the route is still under...
NY 0.57 mi Asphalt
Following the former Ulster & Delaware Railroad (U&D) corridor, the Midtown Linear Park is part of the Kingston Greenline. Running through Midtown between Westbrook Lane and Cornell Street, the ADA...
NY 0.9 mi Asphalt

Recent Trail Reviews

Walkway Over The Hudson

Walkway Courtesy

August, 2025 by wayne7532

Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.

Sussex Branch Trail

diverse & well maintained

August, 2025 by kjfhall61

The trail is ~ 20 miles in each direction. A good mix of paved, gravel, dirt — with minor sections that are “single track”’ish.

Hudson Valley Rail Trail

Great connector trail from New Paltz

August, 2025 by ddylla

This is a great paved trail that connects New Paltz to the Walkway Over the Hudson and then to the Dutchess County Rail Trail. Done together, you can ride for well over 60 miles if you want. The Hampton Inn in New Paltz is a great place to stay with the trail starting just across the street. The hotel also provides easy access to the Wallkill Trail.

Accordion

Heritage Trail (NY)

Nice trail. Poor signage in Goshen

August, 2025 by ddylla

Overall, a very nice paved trail that’s well maintained but very poor connectivity and signage in Goshen. If not for that poor connection, I would have rated this trail five stars. Well worth checking out and hopefully Goshen will improve that stretch in the future.

O&W Trail (PA)

dangerous

August, 2025 by saint2433

started in hancock went 6 miles on rocky dirt road then hit nothing but rocks and impassable biking . no warning signs. please do not attempt

D&H Rail Trail

Wife a I ride this rail trail every chance we get. Very easy ride. Always start in Simpson and ride north to the red caboose and loop back to Simpson. Best part there is a downward grade back to Simpson so it's a breeze with some great relaxation.

August, 2025 by tjs702

Wife a I ride this rail trail every chance we get. Very easy ride. Always start in Simpson and ride north to the red caboose and loop back to Simpson. Best part there is a downward grade back to Simpson so it's a breeze with some great relaxation.

D & H Canal Towpath

Lovely little trail

August, 2025 by nvpierro

Perfect for my elderly dog since we have not been on long walks for the past year. Beautiful scenery of the river, geese flying close to the water, a place to let your loved dog get close to and into the water, and places to sit and just enjoy nature!! Great for MAHA 15 minute walks!

D & H Canal Linear Park and Towpath Trail

Texas Chain Saw Trail

August, 2025 by jilliantor23

The trail was really nice if you went towards Wurtsboro, butttt we originally made the mistake of going the other way and wound up at the Texas Chain Saw House. I thought we were going to be killed by a rapid dog. The trail was very confusing, maybe we weren't going the right way??? It did look like the trail indicated to go straight, but there was a car parked in the middle of the trail and crazy dogs not fenced and only on a rope. I thought it would get loose and tear myself and my dog apart. There's got to be better markings. Or someone needs to figure out a way to make this homeowner happy, because clearly he is disgruntled.

Heritage Trail (NY)

great trail , great maintenance , would recommend

August, 2025 by campinfool

What a wonderful ride , we did a total of 30 miles from Middletown to Chester and back ! Awesome trail wonderful maintenance of the trail!! Would recommend to anyone that wants to ride Loved the many Jonny on the spots and benches along the trail! As well as eating and drinks along the way to buy ! Even a bike repair station on the trail!!!! ¿¿¿¿ Kevin & Pat Bennett

Ashokan Rail Trail

beautiful ride

August, 2025 by campinfool

Awesome ride !!! total 24 miles just breathtaking !!! Trail was wonderful mostly flat , busy with walkers and bikers all friendly !! Pat &Kevin Bennett

D & H Canal Linear Park and Towpath Trail

Great start from Wurtsboro ... but then THIS!

July, 2025 by jason.harry

Sunny and warm July Sunday. Started from the handy parking spaces across from the Wurtsboro firehouse (corner of Pine St. and Canal St.) The informational signs in the little park back toward Sullivan St. are worth checking out before heading north on the trail.

The trail is really nice in that beginning stretch: some gravel, mown grass, hard dirt. Easy on a hybrid or mountain bike ... probably too rough for a road bike. Riding along the long-forgotten, but still totally visible, D&H canal is very pleasant. Some lengths of the canal itself are totally dry and filled with mature trees; other lengths have water. (We didn't stop to read them, but there is fun signage along the way that tells a narrative story about the area.) Mixture of shady tree coverage and open skies. Very, very nice!

BUT THEN! Big surprise. As the towpath crosses McDonald Rd and continues north, which is maybe only 1 mile from the start, the bike path is fully flooded by water and completely unpassable. This is due to a total blockage of water in the canal by a massive beaver dam. (This is right where a home, yard, and outbuildings are visible on the satellite view. And, yes, there are some scary dogs on long ropes ... that come lunging.) The beaver dam is interesting to see, but there is no way to continue on the towpath at that point.

It turns out that the Mamakating O&W rail trail also has an entrance right on McDonald Rd. We chose to ride that back to Wurtsboro. There is a supposed continuation of Mamakating that heads northeast (the satellite view shows it), and it might be possible to jump back onto the D&H trail on the other side of the beaver dam blockage. But the official listing for Mamakating shows that this length is not developed ... so we decided not to chance it.

The Mamakating trail back to Wurtsboro is a straight shot ... no problems. That unintended shorter loop was maybe 3 miles total. But worth it!!

Wallkill Valley Rail Trail

great ride!

July, 2025 by v65xtm2gzt

Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!

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Accordion

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