Bennington, VT Mountain Biking Trails and Maps

498 Reviews

Looking for the best Mountain Biking trails around Bennington?

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

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Activities
Length
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Type
12 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

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Erie Canalway Trail

291.9 mi
State: NY
Asphalt, Concrete, Crushed Stone

Fort Hill Recreational Rail Trail

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

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Hoot, Toot and Whistle Trail

0.5 mi
State: VT
Dirt

Mass Central Rail Trail

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

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
The Glens Falls Feeder Canal Trail begins at the Feeder Dam in Glens Falls and follows the Hudson River through town to the Champlain Canal, then turns south toward Fort Edward. The 9-mile trail...
NY 9 mi Crushed Stone
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
The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
VT 0.5 mi Gravel
When complete, the Erie Canalway Trail will run for 360 miles in upstate New York—from Buffalo in the west to Albany in the east—linking many other communities along the way, including Rochester,...
NY 291.9 mi Asphalt, Concrete, Crushed Stone
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 Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...
NY 2.5 mi Gravel
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
VT 0.5 mi Dirt
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
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

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

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...

Champlain Canalway Trail: Glens Falls Feeder Canal Trail

NY - 9 miles

The Glens Falls Feeder Canal Trail begins at the Feeder Dam in Glens Falls and follows the Hudson River through town to the Champlain Canal, then turns south toward Fort Edward. The 9-mile trail...

Erie Canalway Trail

NY - 291.9 miles

When complete, the Erie Canalway Trail will run for 360 miles in upstate New York—from Buffalo in the west to Albany in the east—linking many other communities along the way, including Rochester,...

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...

Accordion

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...

Champlain Canalway Trail: Glens Falls Feeder Canal Trail

NY - 9 miles

The Glens Falls Feeder Canal Trail begins at the Feeder Dam in Glens Falls and follows the Hudson River through town to the Champlain Canal, then turns south toward Fort Edward. The 9-mile trail...

East Branch Trail (VT)

VT - 0.5 miles

The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...

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...

Erie Canalway Trail

NY - 291.9 miles

When complete, the Erie Canalway Trail will run for 360 miles in upstate New York—from Buffalo in the west to Albany in the east—linking many other communities along the way, including Rochester,...

Accordion

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...

Hoot, Toot and Whistle Trail

VT - 0.5 miles

Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...

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...

Hoosic River Greenway

NY - 2.5 miles

The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...

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...

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...

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...

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...

Erie Canalway Trail

NY - 291.9 miles

When complete, the Erie Canalway Trail will run for 360 miles in upstate New York—from Buffalo in the west to Albany in the east—linking many other communities along the way, including Rochester,...

Hoosic River Greenway

NY - 2.5 miles

The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...

Accordion

East Branch Trail (VT)

VT - 0.5 miles

The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...

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...

Hoot, Toot and Whistle Trail

VT - 0.5 miles

Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...

Champlain Canalway Trail: Glens Falls Feeder Canal Trail

NY - 9 miles

The Glens Falls Feeder Canal Trail begins at the Feeder Dam in Glens Falls and follows the Hudson River through town to the Champlain Canal, then turns south toward Fort Edward. The 9-mile trail...

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...

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...

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

Albany County Helderberg-Hudson Rail Trail

Great trail near the New York State capital

September, 2020 by sschwinn

Great trail in the Albany area! Can't really add to the previous comments. Just note that there is major road construction on Rte 32/ South Pearl St at the eastern end trail head. The parking lot is still open but you may experience delays in getting to it. I would definitely advise not trying to on-road cycle to the trail head.

Delaware and Hudson Rail-Trail

Poultney to Castleton

September, 2020 by gjzambetti

Wonderful trail. Nine miles of crushed stone and hard pack dirt from southern end to Castleton University parking lot. I would not use a thin tire road bike. Beware: the southern end is a dead end 2 miles from Poultney and does not have a parking lot as indicated on the trail map. You must park in Poultney in a well marked lot off of Bentley Ave.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

great ride

September, 2020 by casschoen

We started in Walpole at Blackjack Crossing. First few miles were tough! But the remaining 12 miles into Keene were great. Some great views and remnants of the railroad. Some beautiful cuts in the stone. Highly recommend!

Accordion

Champlain Canalway Trail: Glens Falls Feeder Canal Trail

Warren County bikeway to feeder trail

September, 2020 by SPanny

My wife and I rode the Warren County Bikeway and connected to the Glens Falls Canal trail system on August 31, 2020. The trail meanders a bit through Glens Falls local streets, then we rode on Warren Street a couple of blocks to Shermantown Road and connected to the Feeder Canal Trail. The Feeder Canal trail is a hard packed dirt/stone dust trail that runs along the old canal system…takes you past some old manufacturing plants, working cement plants, etc. Very flat, easy pedaling, you don’t really need a mountain/trail bike. The route we took went around some old industrial areas, past the backyards of some neighborhoods, through some small downtowns. A good amount of shade all along the way. We ended up at the Five Combines park and turned around, so we roughly went 10 miles round trip on this section as well. This is a nice resource for local folks in this area. Definitely check out the Feeder Canal website as it details more about the trail including several different branches you can take for more miles. A nice quiet ride.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Great Ride

September, 2020 by bkersula

I rode the northern section today. Actually started near the Walpole bridge and rode some other snowmobile trails and some side roads to the junction with the rail trail, then on to Keene. Saw no one until I reached the dump. Trail was a lot of fun, but in much better shape south of the dump then to the north. Very slow grade, north of the dump it was great in places and pretty bumpy in others. I rode a basic mountain bike and had no trouble. Heard there was a bad section somewhere but never encountered anything that was really unrideable except one bad embankment. Trail was also easier to follow and more obvious the further south you went, multiple snowmobile crossings further north. This was the first time I tried this sort of thing and I had a very good time. I enjoyed the terrain and seeing where the remnants of the old line.

Ashuwillticook Rail Trail

Beautiful trail

September, 2020 by nhelmer78_tl

The trail is a must do for all! It is smooth asphalt the whole trail. Virtually flat the whole trail. Lots of beautiful spots for photo opportunities. A great little farm store and deli just seconds off the trail to pick up a fantastic lunch and sweets with picnic tables on the trail just minutes away! This is a must do trail. I can’t wait to go back and ride it again.

Ballston Veterans Bike Path

Does The Trick

September, 2020 by lmerfffud

This is my go to trail. Close to home, well kept, god for biking or walking and have always felt safe on it.

Erie Canalway Trail

Amsterdam area

September, 2020 by edpepper99

Trail near Amsterdam is pretty scenic and has potential to be really nice, however, the trail both East and West of Amsterdam was very bumpy in spots with many tree roots pushing thru the old pavement. Some sections need to be repaved.

Ashuwillticook Rail Trail

Exceptional trail

August, 2020 by earth2wayne

Just go!

Zim Smith Mid-County Trail

A Great Trail

August, 2020 by lughnerson

August 2020
Starting in Round Lake at a wonderful parking lot, I rode and enjoyed the entire trail, which is beautifully asphalt paved. Some nice scenery. Finishing at 5:00 pm the local church was playing more than 5 minutes of various tunes, the longest I have ever hear. Definitely worth a visit.

Champlain Canalway Trail: Schuylerville

Better than the map shows

August, 2020 by lughnerson

August 2020
This short trail surprised me; it is better than you expect. Right along the Hudson River and the lock canal, the scenery is beautiful and the little village is charming. Definitely worth the visit.

Ashuwillticook Rail Trail

repacking from adams to Cheshire

August, 2020 by 8br29ttjas

No useful detour. Will be working into fall 2020

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