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Bennington Trails and Maps

678 Reviews

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Ashuwillticook Rail Trail

Looking for the best trails around Bennington?

Explore the best rated trails in Bennington, VT, whether you're looking for an easy walking trail or a bike trail like the Spring Run Trail and Appel Way Trail . With more than 41 trails covering 669 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.

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25 Reviews

Albany County Helderberg-Hudson Rail Trail

Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis...

Length: 8.9 mi

State: NY

Surface: Asphalt, Crushed Stone

27 Reviews

Albany-Hudson Electric Trail

The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to...

Length: 26.6 mi

State: NY

Surface: Asphalt, Crushed Stone

1 Review

Appel Way Trail

Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection...

Length: 1.3 mi

State: NH

Surface: Asphalt

42 Reviews

Ashuelot Recreational Rail Trail

Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey.

Length: 21.4 mi

State: NH

Surface: Asphalt, Ballast, Cinder, Crushed Stone, Dirt

109 Reviews

Ashuwillticook Rail Trail

Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The...

Length: 13.9 mi

State: MA

Surface: Asphalt

11 Reviews

Ballston Veterans Bike Path

This asphalt trail is the legacy of an inter-urban trolley system operated by Schenectady Railway Company (SRC) in the early 1900s. To...

Length: 3.5 mi

State: NY

Surface: Asphalt

0 Reviews

Bennington Rail Trail

Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both...

Length: 1.65 mi

State: VT

Surface: Asphalt, Crushed Stone, Gravel

4 Reviews

Black Bridge Trail

Just north of Albany, the Black Bridge Trail connects the communities of Waterford, Cohoes, and Green Island in eastern New York. As it...

Length: 2.1 mi

State: NY

Surface: Asphalt

10 Reviews

Bog Meadow Brook Nature Trail

This out-and-back rail-trail's beautiful natural setting and informative signage invite visitors to appreciate the importance of wetland...

Length: 2 mi

State: NY

Surface: Ballast, Dirt

Recent Trail Reviews

Ashuwillticook Rail Trail

Update to my 2024 review

August, 2025 by andrix

Update to my 8/2024 review: Remains a TOP trail; At northern end easy parking at the Adams Visitor Center; Saw many signs of beaver activity - dams and huts - but no beavers. The Appalachian Trail crosses at Church Road in Cheshire; At southern end I turn back at the Crane Ave. parking area as, in my opinion, there's not much of interest in the remaining mile or so.

Ashuelot Recreational Rail Trail

I love this trail!

July, 2025 by 6z87r5x5ct

I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!

Ashuwillticook Rail Trail

Love the scenery. There are plenty of rest areas.

June, 2025 by sicnj2al

Love the scenery. There are plenty of rest areas.

Accordion

Erie Canalway Trail

rode from Henrietta to lock 33

June, 2025 by tnuhyllek_tl

Beautiful trail. Well maintained. Headed west from Henrietta first, a little secluded. Only went about 2 miles then headed east to lock 33. Felt safer going east. Full of exercise traffic… love to see that!

Ashuwillticook Rail Trail

absolutely lovely

June, 2025 by sfrankovich

I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.

Ashuwillticook Rail Trail

A fantastic trail

June, 2025 by pjohnromeo

Rode it Friday. The views were beautiful, the trail was in great condition, and the road crossings were not a problem at all. I’ll definitely be riding this one again.

Keene Industrial Heritage Trail

short and delightfully maintained

June, 2025 by erikmurphy1

This portion of the Cheshire rail trail has almost no incline is completely straight and runs past a former major manufacturing complex, which is now vacant. Other sites include Keene police department and Keene ice and American house.

Canalside Rail Trail

Still Partially Closed

June, 2025 by gettinlate

As of 6/3/25 this trail is still closed south of 11th street.
There is a detour indicated, which we tried to follow, but quickly lost track of.
Found another way to access the trail further south, only to realize that we'd gotten onto the part of the trail that was officially closed.
I'm sure this will warrant a higher rating once it has re-opened, but we were more than a bit disappointed today.

Toonerville Rail-Trail

Modest but very nice trail.

June, 2025 by ktrenaud

Did this trail in the summer of 2024. I agree with some of the previous reviewers that signage could be a little clearer but that's a MINOR concern. The ride was quite pleasant & would make a great lunch hour break for locals. Absolutely no issues with road surfaces and traffic on the nearby highway was very light that day so no competing with cars. Very short trail so make sure you have other activities planned. Visit nearby Hoyt's Landing on the CT river for a nice end of ride picnic :-)

Bog Meadow Brook Nature Trail

Better than I expected

May, 2025 by eli290

I’m not a trail master so take this with a grain of salt. I thought the trail was pretty good. I wanted a shorter trail with some scenery and this was good for exactly that. It was starting to rain so it cut my walk short however the trail was pretty well maintained with fresh wooden mulch to cover some of the wet areas. Not a lot of wildlife other than some birds, geese and butterflies. It was very peaceful and I will go back again

Mass Central Rail Trail

Ware to Gilbertville and Gilbertville to Wheelwright

November, 2024 by arno911

Rode the two sections of this beautiful trail today. From the parking spot in the middle of the Ware trail towards Gilbertville is a nice ride along the river. But a short one. Opposite the old factory the trail suddenly ends and there are handwritten signs "Stop, Don´t go further, Private property..." It would only take a few yards to reach the next road to travel on towards Gilbertville. No chance. Shame on you, property owners! (The trailmap shows a way through, but that might be an error?)

Okay, same way back and on to Route 32 past Gilbertville, where the next trailhead is waiting;-)
Smooth surface, well maintained and even good for kids bikes and flat all the way to Wheelwright. 3 nice old bridges. This is one is fully recommended! Absolutely worth it.

Ashuwillticook Rail Trail

Mid-Fall Ride

October, 2024 by willipar

Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.

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