Bennington, VT Horseback Riding Trails and Maps

453 Reviews

Looking for the best Horseback Riding trails around Bennington?

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

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
8 Results
Activities
Length
Surfaces
Type

Ashuelot Recreational Rail Trail

21.5 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Delaware and Hudson Rail-Trail

25.8 mi
State: NY, VT
Asphalt, Cinder, Dirt, Grass, Gravel

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Mass Central Rail Trail

38 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

West River Trail

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand
Trail Image Trail Name States Length Surface Rating
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...
NH 32.9 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi Dirt
The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where you’ll find a 4-mile gap. This border area is known as...
NY, VT 25.8 mi Asphalt, Cinder, Dirt, Grass, Gravel
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
MA 38 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...
NY 3.1 mi Asphalt
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
VT 16.1 mi Asphalt, Dirt, Gravel, Sand

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 30,000 of trail maps
  • Share your trail photos
  • Save your own favourite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Trails by activity

Ashuelot Recreational Rail Trail

NH - 21.5 miles

The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...

Mass Central Rail Trail

MA - 38 miles

The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...

Fort Hill Recreational Rail Trail

NH - 7 miles

Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...

Uncle Sam Bikeway

NY - 3.1 miles

Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...

Cheshire Rail Trail (Cheshire Branch Rail Trail)

NH - 32.9 miles

Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...

Ashuelot Recreational Rail Trail

NH - 21.5 miles

The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...

Delaware and Hudson Rail-Trail

NY,VT - 25.8 miles

The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where you’ll find a 4-mile gap. This border area is known as...

Corkscrew Rail Trail

NY - 3.8 miles

The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...

Accordion

Uncle Sam Bikeway

NY - 3.1 miles

Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...

Mass Central Rail Trail

MA - 38 miles

The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...

West River Trail

VT - 16.1 miles

The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...

Fort Hill Recreational Rail Trail

NH - 7 miles

Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...

Ashuelot Recreational Rail Trail

NH - 21.5 miles

The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...

Corkscrew Rail Trail

NY - 3.8 miles

The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...

Cheshire Rail Trail (Cheshire Branch Rail Trail)

NH - 32.9 miles

Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...

Uncle Sam Bikeway

NY - 3.1 miles

Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...

Accordion

Delaware and Hudson Rail-Trail

NY,VT - 25.8 miles

The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where you’ll find a 4-mile gap. This border area is known as...

Fort Hill Recreational Rail Trail

NH - 7 miles

Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...

West River Trail

VT - 16.1 miles

The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...

Mass Central Rail Trail

MA - 38 miles

The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...

Recent Trail Reviews

Ashuelot Recreational Rail Trail

Sunday ride through the woods (10/6/19)

October, 2019 by toddmichon

Instead of the heavily used trails, l looked for one off the beaten path, so to speak. I found this trail searching for NH trails and was somewhat familiar to the area after going to Monadnock Speedway over the years. I didn't realize this trail runs across the entrance to it. After reading a bit, it seems it is partially a paved trail but only near Keene. Figured I would start at the southern end since it's only an hour from where I live. I found the parking area easy enough and figured I'd start the trail from there which is right across the street. I see that the trail goes south a little more but in all honesty, driving on the road getting to the parking area or after leaving, I couldn't see where you actually get to the trail end. Since it's only a quarter mile more, I didn't bother backtracking to figure it out. Trail is unpaved on the southern end and I had read a few people's comments about how they couldn't get past the speedway since the trail isn't maintained all that well in that area. I went up to where it crosses over Rt. 119 (short distance west from the intersection of Rt. 10) then rode back on the highway back to the parking lot. The trail is a mix of grass, gravel, some mud but not much, soft sand and the like. Looks like they just took the tracks out and cleaned it up a bit and said here you go. It wasn't all that difficult to get through the section I did which was about 8 miles, give or take. I used a hybrid bike and had no real issues. I wouldn't recommend a road bike at all. It was a fun ride, saw all the stuff people had mentioned about the old tracks, rail shed and covered bridge. It was a pretty cool ride. I didn't see any other bikers the whole time I rode through the area and only a 2 other people out walking. I did see a couple devices on the side of the trail which had cables running across it. It appeared to be devices to record how much usage, somewhat like you'd see driving a car across a road. Not sure why they are doing this, it's not like I think they're putting too much into this section if this is the state doing this recording. I wonder if by chance it was paved that it would bring more people in. However, I don't see where those using it would help economically since it's not going into any business areas. Some trails have businesses near it like ice cream stands or convenience stores but this section is not designed for that. Time will tell I guess. Maybe I'll go back next year to see if I can get past the race track area. A good Sunday ride through the woods.

Erie Canalway Trail

Amsterdam to a little past fort hunter

September, 2019 by aparrott58

Rode one way approx 7 miles starting in Amsterdam. While pedaling under the thruway overpass, it smelled like feces/urine. This area has an abandoned building and an adjacent overgrown wareyard with debris piles, junk and very weedy. Approx 1/3 mile past the overpass we stopped to look at map and weather app (the clouds were looking ominous) and I see a large man riding toward us (up until that point we saw no-one else on the trail). As he passed us grunting and snarling at us, I noticed he was filthy with dirty hair and face. He rode past us and less than 30 seconds later when I looked down the trail, he had disappeared into the brush (this is a straightaway section - you can see a long way). We turned around and within 10 minutes the downpour was upon us. We were soaked when we arrived back in am-dam.

My advice: do not pedal this section by the overpass alone. This man had no good reason to pursue us, then growl/grunt when passing us and then disappear back into the brush. If I had been solo riding, I can only speculate on a different outcome. He is living under/by the overpass. We apparently pedaled thru his "area".

Ashuwillticook Rail Trail

Really nice

September, 2019 by donjfarr

First what this isn't...an "off road" trail. No dirt or gravel.
However if you want a beautifully maintained paved bike path, then you found it.
Extremely flat with a variety of scenery from forest to wetlands to lakes to old industrial.
A lovely ride

Accordion

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Excellent gravel trail.

September, 2019 by justin.raymond.14

Started in Fitzwilliam near MA border and road to Keene and back. Used a road bike with 25mm wheels. If you are comfortable riding dirt/gravel on a road bike the trail is quite easy to ride. Some sections were muddy despite not raining recently. I imagine those sections would be more technical after a rainstorm.

Erie Canalway Trail

Part 1, Albany to Schenectady, Lock 7

August, 2019 by lughnerson

This is the first of a multi-part review, since the trail is so long. It takes me and hour and a half to drive from New Paltz, NY to one of the parking areas.

Last year I rode the section from the Corning Center in Albany along the Hudson River to end at a parking lot in Watervaliet. Right next to the the river, there is a lot to see and hear on this paved trail, as the highway is sometimes very close. There are plenty of areas to stop and touch the water while on a break. Just do it sometime anytime. I would like to revisit this section after the leaves have fallen, just before winter.

Last month I rode from the through the Albany suburbs of Watervaliet, Green Island, and Cahoes. Though it is fairly flat and well paved, it is totally on-street section of the trail. One nice side trip is north up to Waterford, which goes over several bridges to Van Schaich Island and Peebles Island. When you cross the steel bridge you can see the beginning of the actual canal and its first lock near the Waterford Harbor Visitor Center. Just go down Cannon Street.

Last week, Tuesday August 20, 2019 I went to the section that includes the towns of Latham and Colonie, turning around at Lock 7 on the Mohawk River. This is a very nice section of the trail, good pavement, mostly shady and offers a few nice views of the Mohawk River. There is a short on-road section in Dunsbach Ferry where you ride underneath Route 87. Then a significant hill back to the trail. Headed west, from the Lions Park in Niskayuna ( a good parking area) there is one very straight and flat section of about a mile or so for time-keepers and racers. Lock #7 is a pleasant park to stop for a break and watch the boats navigate the rise or fall of the lock, next to a waterfall.

It may take several years for me to complete the entire Erie Canal trail, but it is a fun goal.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Another NH Mountain bike trail

August, 2019 by ca959709

Rode this trail heading northwest from downtown Keene.This trail is fantastic when in the center of town. As soon as you cross Hurricane rd., however, the trail surface degrades, becoming sandy and eventually very rocky around the landfill, where we turned back. I was riding a gravel bike with 38 inch tires, but it's pretty clear that this trail is mountain bike only unless you want to walk your bike through a number of very rocky sections.

Erie Canalway Trail

Herkimer to St Johnsville

August, 2019 by francebau

We have been loving this trail from Herkimer ( starts at Movac parking lot rt 5s Mohawk) , past Fort Herkimer Church about 4 miles is paved and mostly flat. A beautiful ride. Will be great when the connection at rt 167 in LittleFalls is finished. The trail continues to be paved across rt 167 ( Little Falls). Mostly flat and very scenic. Turns to stone dust at Finks Basin rd. LF ( parking). Paved again@ STJ

Albany County Helderberg-Hudson Rail Trail

GREAT TRAIL!

July, 2019 by mhammer323

My son and I stopped to the Voorheesville trailhead which is considered the end of the trail. We biked from here to the start of the trail in what's considered Albany. This is a great trail. From the beginning in Albany to Voorheesville is slightly uphill going but the way back is more of downhill feel (this coming from my 12 year old son). He did say this is one of his favorite trails we've ever done! They have bikers tools and air pumps at the beginning of this trail which is cool. Lots to see also along this trail. Will definitely make the travel to do this trail again! As described it is 9 miles each way.

Erie Canalway Trail

Section Amsterdam to Sprakers

July, 2019 by vikkb34

We startes in Amsterdam,we parked on a dirt section on Cleveland Ave,little further down is a bigger paved lot.We did a little detour on Bridge Rd,nice pedestrian bridge(flowers & a few interesting sculptures.) Rode into Riverlink Park. Small park,but a cute little detour. Most of the trail was paved,there was a section that was bumpy.Pretty flat. About 4-5 miles was crushed stone/dirt.If it rained heavy may get muddy.We enjoyed the trail,a few street crossings.Was a pretty quite trail on a sunday.Was a mix of shade & sun. We seen some wildlife,seen a fisher & what looked like a weasel,was so quick.,so that was cool!.We rode to Sparkers. There was a cooler of waters & there was bathrooms across the street.(Courtesy of the church)We rode about 44 miles there & back,with detour. The trail is broken up into sections,so we rode this section. Hope to ride the Buffalo section..

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Challenging but fun - use a mountain bike

July, 2019 by troyknielsen

I started at the southern portion of the trail. I rode a gravel road / light touring bike (Specialized Sequoia) and it was fine but in hindsight I would have done a bit better with the FatBoy. There was a fair amount of sand in the first portion of the trail. I encountered some decent sized muddy sections but nothing crazy. The variety of scenery is great and the trail is very quiet. I encountered about 3 other bikes and a couple of people walking. I wouldn't do this trail if there's been significant rain in the past few days because of the pooling that I saw in some of the sections flanked by rock walls. And I rode in July and was flanked by large flies seemingly at all times. But given the challenge and scenery it's worth it!

Fort Hill Recreational Rail Trail

Lovely trail but not well-maintained toward the end

July, 2019 by jennifer.thompson.unity

My daughter—an inexperienced biker—and I enjoyed the diverse landscape and beautiful views along the Connecticut River. However, because the trail was so overgrown and rough for the last mile or so, we didn’t make it to the end to see the historic bridge.

Mass Central Rail Trail

Norwottuck Branch (Belchertown to Northampton)

July, 2019 by lughnerson

Tuesday July 09, 2019, 5:30 pm.
Weather 88' F, low humidity, very light clouds.

Great weather for riding this great trail. Massachusetts really sets the bar for bike trails. This one has a line down the middle to help the careless riders better their performance. There are benches near view spots with poems and examples of flora and fauna carved into boulders. There are granite mile markers on both poles and pavement stones at the side of the trail. The pavement was very smooth and there are only some slight inclines. Tunnels and bridges, a variety of scenery, this is both a community trail and a destination trail. I drove 2.5 hours for this one and the much shorter Canalside trail a half hour away in Turner Falls, doing both on the same day with a mid-trip visit to the Bridge of Flowers in Shelburne Falls. All 3 places worth the trip, but now I have to complete the other sections of the Mass Central Greenway. Good job Massachusetts!

Find Nearby City trails

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

OR

Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!

Register with Google

OR