Bennington, VT Mountain Biking Trails and Maps

711 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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Length
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13 Results
Activities
Length
Surfaces
Type

Erie Canalway Trail

335.2 mi
State: NY
Asphalt, Concrete, Crushed Stone

Mass Central Rail Trail

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

West River Trail (Windham County)

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Ashuelot Recreational Rail Trail

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

Cheshire Rail Trail (Cheshire Branch Rail Trail)

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

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

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

East Branch Trail (VT)

0.5 mi
State: VT
Gravel
Trail Image Trail Name States Length Surface Rating
Closure Notices: In Palmyra/Wayne County, a portion of the trail is closed between route 21 and Swift Landing Park. InĀ Oneida-Verona, Oneida County, a bridge replacement is taking place at the corner...
NY 335.2 mi Asphalt, Concrete, Crushed Stone
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. The Mass Central Rail Trail runs for 64 miles between...
MA 72.2 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
Closure Notice:Ā Due to flooding, the Ashuelot Recreational Rail Trail is closed from Sawyers Crossing Road heading southwest to Holbrook Ave (near Swanzey Lake Road) until further notice. Please see...
NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of uses,...
NH 42.4 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where there is a 4-mile gap. This border area is known as the...
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 Glens Falls Feeder Canal Trail is a 9-mile trail through Glens Falls, New York. The town is just south of the entrance to the Adirondack Park and Lake George. About the Route The Glens Falls...
NY 9 mi Crushed Stone
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
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
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 2.3 mi Dirt
The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...
VT 18.1 mi Dirt
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

Recent Trail Reviews

Ashuwillticook Rail Trail

Great Trail

October, 2026 by pokeystache

We rode from Pittsfield to Adams and back. Very nice trail. 50% shaded. Ate lunch at AJā€˜s at Adams. Nice restaurant in an old train depot. Limited parking at the beginning in Pittsfield. Start your ride at the next parking area to the north. Lots of lakes and rivers running next to the trail. Asphalt the entire length of the trail.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

The good: it’s being paved. The bad: signage through Keene

October, 2026 by pammer1959_tl

We hoped to do the entire trail by parking in the middle just south of Keene. The signage going through town was minimal and included being on the road quite a bit. The south side noted ā€œroad closedā€ because it’s being paved, but the road dead ended after 2 miles.

Disappointed is an understatement.

Erie Canalway Trail

Portapotty at Desmore Rd, east of AlbionAnd others not shown

September, 2026 by gardell

Portapotty at Desmore Rd, east of AlbionAnd others not shown

Accordion

Ashuwillticook Rail Trail

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

September, 2026 by sicnj2al

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

Warren County Bikeway

The climbs were not easy for casual riders. Also, riding on a road with fast traffic.

September, 2026 by annzee.shepler

The climbs were not easy for casual riders. Also, riding on a road with fast traffic.

Ashuwillticook Rail Trail

Top Notch Trail

August, 2026 by trylondm

Biked end to end on a beautiful summer day. An absolutely beautiful paved trail with lots of water features to see - lakes to the south, river further north, and views of the mountains. Nice trailside pub in Adams and other eateries, including ice cream. Well-loved, with lots of walkers and skaters, as well as riders. Benches and picnic tables aplenty. One of the best trails I've had the privilege to ride. The only way it could possibly be better is if it was longer.

Correction to someone else's review: trail goes gently downhill south to north (not north to south) from Cheshire to Adams.

Catamount Trail - Sections 1 and 2

Catamount Trail Section 2

August, 2026 by awrootbeer

If you are a dedicated mountain biker than this would be a 5 star. Don't do this trail if you don't have a mountain bike or those fat tires. I was on a mountain bike, and my son had a regular bike. The beginning of the trail is easy and lovely. Once you connect with the trail (beautiful water views) the trail becomes mostly rock with some sand. Passed 1.8 miles the trail is impassable with our bikes. Somehow we made it out and back without falls or bike damage. I have biked other ski trails that were more compacted sand and dirt with some rock. This is not that kind of trail.

Zim Smith Mid-County Trail

Loved this trail easy to ride. Well paved and clean. Will do this again and again.

August, 2026 by lynmcd33

Loved this trail easy to ride. Well paved and clean. Will do this again and again.

Ashuwillticook Rail Trail

Well maintained trail with great views

August, 2026 by sebastianmhill

Awesome trail. Smooth surface and great views. Also lots of different places you can join the trail. We started a little further north to skip the more industrial part of the trail.

Mass Central Rail Trail

Hadley to EastHampton- Norwottuck Rail Trail

August, 2026 by jlwinetrout

Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.

Ashuelot Recreational Rail Trail

Rough ride

July, 2026 by mroschella

Trail lacked any evidence of maintenance. Rode from Hinsdale to Winchester.

Manhan Rail Trail

Difficult to find the trailhead from Northampton but once you do....

July, 2026 by janieo

The Northampton part, which is reallly the NORWATTUCK RAIL TRAIL is really 2 stars bc it's so confusing. Needs fundraising and signage. But the rest, Manhan Rail Trail, is really nice. 5 stars. We took photos to illustrate but I unfortunately deleted them by accident.

We had stayed at the Hotel Northampton & nobody could tell us for certain how to find the trail other than to mention the railroad tracks. We found a paved path by the tracks & headed left. We passed a stone that said <- BOS/NHV --> and that's all. (Couldn't imagine how Boston could be to the left or straight ahead.) Within about 20 minutes, that path ended by some really rundown stores. On an aerial Google map, it reads as NORWATTUCK RAIL TRAIL (& shows it as a hiking &rail trail on the east side of the railroad tracks) but there is no signage anywhere to guide you. So when we got to the end, we turned around & headed in the other direction (south). THIS NORWSTTUCK TRAIL definitely needs some help. (Or maybe some day to be extended.)

Back to where we started out & this time heading in the other direction the trail actually becomes nice & very well marked. It seems to become the NEWHAVEN AND NORTH CANAL RAIL TRAIL (BUT there are no signs to this effect).

Where you meet the MANHAN RAIL TRAIL the signage is very clear, even as you are going through a village center or crossing a street or road, & the trail is very nice. You're following the reservoir & get some nice riding in.

We just kept going until we reached Easthampton. There you can even pick up trail maps! Ride on, and by the Municipal Bldg there's a nice park & large pond where you can see Mt. Tom behind it. Lovely, relaxing, scenic.

Then the ride back to Northampton but this time we knew the trail well & just enjoyed it.

North of Ferry St., at Lower Mill Pond, the Manhan Trail branches off and follows the river, eventually reaching the Connecticut River & Mt. Tom State Reservation. Should be a lovely ride! (You can also turn off here when you're riding south from Northampton.

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