Bennington, VT Running Trails and Maps

649 Reviews

Looking for the best Running trails around Bennington?

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

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Activities
Length
Surfaces
Type
41 Results
Activities
Length
Surfaces
Type

Albany-Hudson Electric Trail

36 mi
State: NY
Asphalt, Crushed Stone

Ashuwillticook Rail Trail

13.5 mi
State: MA
Asphalt

Ballston Veterans Bike Path

3.5 mi
State: NY
Asphalt

Black Bridge Trail

2.1 mi
State: NY
Asphalt

Bridge of Flowers

0.1 mi
State: MA
Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Champlain Canalway Trail: Schuylerville

2 mi
State: NY
Crushed Stone

Erie Canalway Trail

335.2 mi
State: NY
Asphalt, Concrete, Crushed Stone

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Manhan Rail Trail

6 mi
State: MA
Asphalt

Mass Central Rail Trail

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

Railroad Run

0.5 mi
State: NY
Asphalt

Spring Run Trail

1 mi
State: NY
Asphalt

West River Trail

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

Zim Smith Mid-County Trail

11.5 mi
State: NY
Asphalt

Ashuelot Recreational Rail Trail

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

Champlain Canalway Trail: Fort Ann

1.68 mi
State: NY
Asphalt

Champlain Canalway Trail: Saratoga

1.5 mi
State: NY
Crushed Stone, Dirt
Accordion

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 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

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

Warren County Bikeway

10 mi
State: NY
Asphalt

Bog Meadow Brook Nature Trail

2 mi
State: NY
Ballast, Dirt

Champlain Canalway Trail: Waterford

6.7 mi
State: NY
Asphalt, Crushed Stone, Gravel

Cohoes Heritage Trail

0.6 mi
State: NY
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Appel Way Trail

1.3 mi
State: NH
Asphalt

Jim Tedisco Fitness Trail

0.5 mi
State: NY
Asphalt

Valley Trail

9.1 mi
State: VT
Asphalt, Dirt, Gravel

Bennington Rail Trail

1.65 mi
State: VT
Asphalt, Crushed Stone, Gravel

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Rocky Hill Trail

0.9 mi
State: MA
Asphalt
Trail Image Trail Name States Length Surface Rating
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
NY 9 mi Asphalt
The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
NY 36 mi Asphalt, Crushed Stone
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 13.5 mi Asphalt
This asphalt trail is the legacy of an inter-urban trolley system operated by Schenectady Railway Company (SRC) in the early 1900s. To attract visitors on weekends, SRC built an amusement park at...
NY 3.5 mi Asphalt
Just north of Albany, the Black Bridge Trail connects the communities of Waterford, Cohoes, and Green Island in eastern New York. As it parallels Delaware Avenue, it is sometimes referred to as the...
NY 2.1 mi Asphalt
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
MA 0.1 mi Concrete
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
MA 3.6 mi Asphalt
The Schuylerville segment of the 71-mile Champlain Canalway Trail rail runs between Schuyler House, past Lock 5 of the canal and does a loop around the island (Hudson Crossing Park). As of 2011, only...
NY 2 mi Crushed Stone
Closure Notices: In Palmyra/Wayne County, a portion of the trail is closed between route 21 and Swift Landing Park. In Oneida-Verona, Oneida County, a bridge replacement is taking place at the corner...
NY 335.2 mi Asphalt, Concrete, Crushed Stone
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
NH 0.9 mi Crushed Stone
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
MA 6 mi Asphalt
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 60 miles from Boston to Northampton...
MA 59 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The Railroad Run trail runs for just a half mile between West Circular Street and Congress Avenue in Saratoga Springs. The trail is part of a growing network throughout the town and county. There are...
NY 0.5 mi Asphalt
Currently, the 1-mile Spring Run Trail extends between East Street just south of Excelsior Avenue and I-87, or the Northway, near Exit 15. Eventually, the trail will begin in Congress Park and run...
NY 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
Popular with residents of Saratoga County who commute under their own power or love to exercise outdoors, the nearly 12-mile Zim Smith Mid-County Trail is considered the backbone of a growing trail...
NY 11.5 mi Asphalt
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
Known for its picturesque beauty and rich history, the Town of Fort Ann is part of the Champlain Valley National Heritage Area, a federally designated area stretching between the Hudson Valley and...
NY 1.68 mi Asphalt
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
The Saratoga segment of the 71-mile Champlain Canalway Trail includes three disconnected segments near the Hudson River, from Stillwater Township to the town of Saratoga. The longest section is under...
NY 1.5 mi Crushed Stone, Dirt
Accordion
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 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 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 heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
VT 2.2 mi Gravel
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
VT 3.2 mi Asphalt
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
Visitors can expect a couple of easy climbs as they travel on the Warren County Bikeway through the southern Adirondacks for 10 miles between Glens Falls and Lake George. It’s well worth the effort,...
NY 10 mi Asphalt
This out-and-back rail-trail's beautiful natural setting and informative signage invite visitors to appreciate the importance of wetland habitats. Located just east of downtown Saratoga Springs, the...
NY 2 mi Ballast, Dirt
The Waterford segment of the Champlain Canalway Trail begins on the Mohawk River at the Old Champlain Canal Lock 4 and continues north following the old canal towpath past Lock 7 to Upper Newtown Road...
NY 6.7 mi Asphalt, Crushed Stone, Gravel
The Cohoes Heritage Trail is less than a mile long but serves as a significant local connector: it provides a way for people to travel between the riverfront to the Mohawk Hudson Bikeway. The northern...
NY 0.6 mi Asphalt
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
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 between Wheelock Park on the trail's west end and Ashuelot River...
NH 1.3 mi Asphalt
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
NY 0.5 mi Asphalt
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
VT 9.1 mi Asphalt, Dirt, Gravel
Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both recreation and active transportation. Following a former...
VT 1.65 mi Asphalt, Crushed Stone, Gravel
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
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
NH 1 mi Asphalt
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
MA 0.9 mi Asphalt

Recent Trail Reviews

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Accordion

Erie Canalway Trail

Medina NY to Gasport NY

September, 2023 by mconlon1

About a 45 minute ride on the Erie Canal path ,starting at the Medina lift bridge, through farmland and villages (Middleport, Gasport) herons that are absolutely not afraid of you! Beautiful in the fall!

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

just walked the D & H trail from granville center to middle granville. really enjoyed the walk out toward middle granville but on the way back while walking through the farm (which was a delightful experience on the first trip through, seeing calves and cows) but then were charged by two pitties which attacked my dog and knocked me down. Luckily I had an umbrella and was able to get up and get away and down the trail. the dogs followed for a while but then returned to the farm. Too bad because was a very enjoyable walk until this. I just hope these two dogs dont really hurt someone....

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

Ashuwillticook Rail Trail

great trail

September, 2023 by dpwrztjhrw

Asphalt smooth and trail is terrific. Easy, flat trail with some water views passing Silver Lake/Pittsfield.

Ashuelot Recreational Rail Trail

South from Keene

August, 2023 by frankieoengine

A nice 5 miles to a huge wash out shutting down the trail. We bypassed the closure using the road for 1/2 mi. Only to find another sign saying trail closed. Turned around , do not plan on going more than 5 mi from Keene! Frankie

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Great trail even after a bad weather summer

August, 2023 by twelch11

Wonderful! the section north of Keene is just great. I admit there are a very few spots that are a little rough or a little wet but for 99% of it, anyone with even limited experience will enjoy it. I would not recommend this trail for a road bike although there are sections that are smooth enough for one. The only part that was a little concerning was near the landfill just north of Keene but that was only 2 tenths of a mile long and if concerned, you could easily walk your bike through that area. But honestly, the entire trail was great with several spots offering spectacular views. The surface is mixed depending on the area, some areas had grass while others were course sand. There were a couple rocky areas but those spots are few and very short.

Hoot, Toot and Whistle Trail & Riverwalk

great little trail

August, 2023 by jgosses_tl

Nice trail through the woods that opens up at the end at the boat launch for the Harriman Reservoir. Definitely not .5 miles; more like 3 miles out and back.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Good trail in a challenging year

July, 2023 by twelch11

Went from the southern end at State Line Circle to Rockwood pond. Once you go past the Fitzwilliam Fire Department/Fitzwilliam Station it starts to get a little rough through and past Royalston Road and Richmond Road with steep hills at each road crossing and pretty much unmaintained trail. Then it smooths out up to Rockwood Pond. Rockwood pond is a very nice stretch with great views of Monadnock to the east. Great trail that needs a little work. Very manageable with a mountain/fat tire bike. Wouldn't try it with a street bike. Most enjoyable trail.

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