Bennington Running Trails and Maps

411 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
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36 Results
Activities
Length
Surfaces
Type

Albany County Rail Trail

8.4 mi
State: NY
Asphalt

Appel Way Trail

1.3 mi
State: NH
Asphalt

Ashuelot Recreational Rail Trail

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

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Ballston Veterans Bike Path

3.5 mi
State: NY
Asphalt

Black Bridge Trail

2.1 mi
State: NY
Asphalt

Bog Meadow Brook Nature Trail

2 mi
State: NY
Ballast, Dirt

Bridge of Flowers

0.1 mi
State: MA
Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Champlain Canalway Trail: Saratoga

1.5 mi
State: NY
Crushed Stone, Dirt

Champlain Canalway Trail: Schuylerville

2 mi
State: NY
Crushed Stone

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

279.5 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
Accordion

Jim Tedisco Fitness Trail

0.5 mi
State: NY
Asphalt

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

38 mi
State: MA
Crushed Stone, Dirt, Grass

Railroad Run

0.5 mi
State: NY
Asphalt

Spring Run Trail

1 mi
State: NY
Asphalt

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

Valley Trail

9.1 mi
State: VT
Asphalt

Warren County Bikeway

10 mi
State: NY
Asphalt

West River Trail

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

Zim Smith Trail

9.2 mi
State: NY
Asphalt, Crushed Stone, Dirt
Trail Image Trail Name States Length Surface Rating
More than 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is open and paved. Pedestrians and bicyclists may use the trail and, in the winter...
NY 8.4 mi Asphalt
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
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
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 11.9 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
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 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 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 8-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
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
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
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, Syracuse, Rome,...
NY 279.5 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
Accordion
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
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 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 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 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 9.6 mi Asphalt
A 104-mile rail line was shattered by hurricane in 1938. Today, the corridor is being developed as the Mass Central Rail Trail to be enjoyed by bicyclists, walkers, joggers, and cross-country skiers....
MA 38 mi Crushed Stone, Dirt, Grass
Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
MA 10 mi Asphalt
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
MA 4.9 mi Asphalt
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 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
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 Route 100....
VT 9.1 mi Asphalt
This trail is as smart as it is pretty. Signs that detail the area's history and appealing destinations accompany a scenic ride from Glens Falls into the resort town of Lake George, New York....
NY 10 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
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Trail, sometimes called the Zim Smith Mid-County Trail, connects the towns of Halfmoon, Round Lake Village,...
NY 9.2 mi Asphalt, Crushed Stone, Dirt

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Trails by activity

Recent Trail Reviews

Fort Hill Recreational Rail Trail

A Bit of A Challenge

August, 2018 by kerund

This trail seems little-used. Rode a gravel bike starting at the parking lot at the south end. Several trees down in the trail and some puddles and running water (to be fair, it had rained the night before). The trail surface varies and while it’s manageable, this isn’t a trail for someone looking for a leisurely rail trail cruise. Nice views of the Connecticut River.

Valley Trail

Very Misleading Entry

August, 2018 by chuck1956

The entry leads you to believe there is a 9 mile asphalt trail linking two towns in a Vermont valley with just a small gap near the north end. Unfortunately, there is no such thing. The trail is a very confusing series of blue signs which go through the woods on dirt (mud) tracks, over grass lawns with no identifiable trail, and on busy and narrow town roads (the only asphalt on the trail). Talking to locals, we discovered that parts of the trail are used for mountain biking, but that the idea of a continuous trail linking West Dover and Wilmington is a dream that has yet to be realized.

Ashuelot Recreational Rail Trail

From Keene to West Swanzey the trail is great for biking.

July, 2018 by baijudy

From West Swanzey toward Winchester, trail isn't as good for biking as it has not been improved as much as the Keene to West Swanzey portion.
There are two errors in the directions:
About 2.5 miles past the pedestrian bridge, you’ll cross Sawyers Crossing Road, where the circa 1859 Cresson Covered Bridge sits about 500 feet to the right (should read 'to the left'). The trail crosses the river in 0.3 mile near West Swanzey in an area considered moose territory. Passing on the east side of West Swanzey, a 0.3-mile detour right onto Christian Hill Road (should read 'right onto Railroad Street and then right onto Main Street which') leads to the 1832 Thompson Covered Bridge. (FYI: Main Street becomes Christian Hill Road at the bridge over the rail trail and one cannot turn right or left onto either road because the trail passes well below the road level).

Accordion

Ashuwillticook Rail Trail

What a wonderful trail

July, 2018 by mmoran56

My wife and I rode this trail from one end to the other. The scenery was beautiful, the ride was easy and the people were nice. Lots of lake views. Some hills but not difficult. Parking was a small challenge but not impossible. I would do it again in a minute.

Erie Canalway Trail

Riverwalk Bike Path, Tonawanda, NY

July, 2018 by johntodd104

Although this Bike Path is scenic, it is NOT maintained, it is continues wide cracks in the pavement and huge bumps. I already saw a couple bickers fall because of the neglected pavement. Not only do you risk a fall because of the neglect, you also risk damage to your tires as the bumps & cracks are severe. I have a Road Bike, and changed my tires because of the bumps, also note the bumps also can shift your gears.

Ashuelot Recreational Rail Trail

Over-Grown

June, 2018 by jjr1956

Hi Guys!
I started this ride at the Hinsdale trail-head. Big mistake! The trail is poor and the vegetation is overgrown. It had to be over 2 feet high. There is a very small area to ride that's about a foot wide. Otherwise, it's very hard to ride and stay out of the vegetation. It was also very, very buggy for some reason. I know it's summer and bugs are out there, but it was unusually buggy. I used a lot of bug spray, but it didn't matter. The little suckers wanted me and got me. It is a very pretty area of the state, but I wouldn't go back until the fall, or maybe starting from the northern start point. I'm new to biking and can not do the whole length of this trail yet.

Ashuwillticook Rail Trail

Worth a long drive

June, 2018 by lughnerson

Yup. August 2017, hot summer day.
Riding along the lakes or reservoirs, it is nice and flat, paved well. A good trip.

West River Trail

Appears to be alot of conflict with landowners

June, 2018 by gregswild

The trail definitely has some potential if there was more participation from landowners, some of whom appear to be quite hostile to the idea. It appears that the trail did or attempted to cross through private land on the Townsend section northward towards a connection with the Jamaica section but you soon run into a labyrinth of blocked trail and more No Trespassing and Posted signs than I have ever seen in one spot anywhere in my life. They did dissuade me that day and I turned around which is most unfortunate. Laws being what they are in Vermont, there is nothing illegal about this of course. In many states, including Texas surprisingly there is a law against closing off a certain amount of shoreline areas to passersby and swimmers etc. in order to promote this activity which is ultimately beneficial to all, locals and visitors alike.

Warren County Bikeway

Pretty good and worth the time

June, 2018 by prhelt

The northern half is by far the best. The southern part is not well marked, has some long road sections and dumps you in town with nothing around. It is well paved and taken care of. The northern part goes to Lake George and is very nice. For someone seeking a short ride, I would start at the outlet center and ride north. That is about 8 to 10 miles round trip depending on how much you ride around town.

Erie Canalway Trail

Resurfacing Green Lakes to Canastota

May, 2018 by cnyriv

I've ridden this section for more than 30 years with no flats. New aggregate has been laid down in this section over the last three weeks. It sparkles in the sun. I've had five flats on the new surface. Each was caused by a tiny glass shard, some clear some brown. The workers said they were putting down crushed limestone. It seems to there may be recycled glass in the mix. I'm running Schwalbe G one 700x60 tires at 30# rear 25# front. It's an admittedly light tire but I've had no problem with flats elsewhere including rough gravel roads. Go belted or tubeless on this section or be prepared to flat. Without the nice smooth new surface I'd have given this trail four stars.

Erie Canalway Trail

Erie Canalway Towpath is a Diamond int the Rough

May, 2018 by mdenettesr

Six older couples cycling from East Syracuse to Albany in May, just before the Canal opened. Advantage: Lots of camping. Disadvantage: no boats to watch in the locks and towns. The book was pleasantly wrong and needs a wee bit of an update with the wonderful new additions, trail re-locations, and especially attractions. There was much less on-road cycling than we had worried about. The drivers on the road were suitably accommodating. We camped some nights and stayed in motels as the mood and weather might indicate. When we got to Amsterdam, NY, however, we slept in a CASTLE!! The Amsterdam Castle, a mere 800' from the trail was amazing and worth the few dollars more than the chain motels we had stayed at. There was a breakfast and wonderful rooms. The artwork was worth a museum entrance fee. Everything was AMAZING! We enjoyed a nice meal at Parillo's Italian Restaurant (go through through the Armory Bar and Grill and take a left). Another fun culinary highlight of the ride was Mike's Diner in Fultonville. It's just under the highway on the left. Great food, great fun. Very entertaining proprietor and a fair price. Now, the areas that need improvement: Only one or two cross streets were signed. There were virtually no signs for important trail-side amenities, like, lodging, camping, ice cream, groceries, repair shops, ice cream, attractions, or restaurants with ice cream. [The Great Allegheny Passage really got that right.] ECT should take a look. There were no trail-side tool set-ups like on the Norwootuck or GAP trails. Those were nice. Some of the really cool attractions, like the first bike ridden cross-country, a huge high-wheeler, is in the second floor of a darling historical society in Henniker. Each local Chamber of Commerce should be all over this trail. As multi-day trails go, this one had the most to offer in scenery and museums, but they were often not in the book and hard. We only knew about them from prior research and our AAA Guide. Rome and Fort Stanwix not withstanding. We broke a chain on the tandem in Schenectedy. One bike shop, Plaine and Sons, fortunately has a mobile service van. We called them and explained the issue, and they don't actually use the van. It's basically just a sign. We went to NY Bike on Congress, where an efficient young man repaired the bike in less than five minutes. If an establishment isn't really going to support the trail, they should not be mentioned. My advice would be double your time from other trails of the same length and see the sights which lie not far off the trail. This ride is more of an adventure and less of just a bike ride. To just ride it is to miss the mark. Hope some of this helps. Happy trails.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

North End - Walpole trail head

May, 2018 by ryoung_tl

Clear sunny day in May. Excellent conditions with sunshine and a gentle breeze to keep away the bugs. No ticks encountered. Walked 3.5 miles from the Blackjack Crossing trailhead.

Trail is in great shape although the first .25 mile (going north to the very end from the parking area at the end of Blackjack Crossing) is overgrown and a bit muddy. The first .25 mile stretch going south is the same, but then the surface is very good with crushed rock. There are muddy spots as you pass through the deep cut areas, but other wise, excellent. We walked but mountain bikes would fare very well. Road bikes NOT recommended.

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