Find the top rated trails in Bennington, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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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....
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...
At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail...
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...
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...
Given its covered bridges, historical aura and abundant wildlife, the Ashuelot Rail-Trail (a.k.a. Ashuelot River Trail) has plenty to offer. The 21.2-mile route follows the corridor of the Ashuelot...
About 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is now open. Pedestrians and bicyclists may use the trail and, in the winter months, the...
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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...
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The Cheshire Rail Trail stretches for nearly 33 miles between Route 12 near Bookseller Road and the New Hampshire–Massachusetts state line at Route 12. In Keene, the trail includes a beautiful stone...
Canalside Trail begins at McClelland Farm Road and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a half mile north...
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...
Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
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...
The Toonerville Rail-Trail (a.k.a. Springfield Greenway) spans 3 meticulously maintained miles from the downtown business district of Springfield southeast to the western bank of the Connecticut River...
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...
The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
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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....
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...
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...
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
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...
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...
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....
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...
The Cheshire Rail Trail stretches for nearly 33 miles between Route 12 near Bookseller Road and the New Hampshire–Massachusetts state line at Route 12. In Keene, the trail includes a beautiful stone...
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The East Branch Trail is a 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...
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...
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,...
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...
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...
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,...
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...
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...
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...
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,...
The Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...
Canalside Trail begins at McClelland Farm Road and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a half mile north...
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...
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...
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,...
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...
The East Branch Trail is a 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...
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...
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,...
About 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is now open. Pedestrians and bicyclists may use the trail and, in the winter months, the...
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...
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...
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...
Canalside Trail begins at McClelland Farm Road and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a half mile north...
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
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...
The Delaware & Hudson Rail-Trail quietly rambles over the rolling hills and farmland of western Vermont along the state’s border with New York, dipping into its western neighbor at the community of...
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....
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....
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...
At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail...
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...
Love this trail, we have been on it many times going from Lanesboro to Adams and back. The trail is well kept, the air is fresh and clean plus it always seems a bit cooler, which is important on those hot summer days, plus the views are spectacular.
Recently about 1 mile in I got a flat, I turned around loaded my bike back on the rack and drove to the bike shop in Adams. The store was closed but the owner was outside in his car, just about to leave. He spotted me going to his front door, so he got out asked what was wrong and proceeded to reopen his store to fix my flat. It was not an easy repair, rear tire that had been on the bike for a while. He persisted, completed the repair and charged me a very reasonable rate for tube and labor.
I could not be more thankful...I got back on the trail right out his front door, rode down to Lanesboro and back to Adams where I had a very nice dinner at a trailside restaurant. Perfect ending!
Very rocky trail. It's labeled moderate but should be moderate/difficult. The trail is through woods with limited views. The Falls are impressively highland nice. I'm glad we went but wouldn't do it again.
This portion of the trail is well maintained and is a pleasure to ride. The slightly (2% grade) uphill run north was of benefit for the obviously downhill ride back to State Line - a ride of just over 20 miles.
This portion of the Cheshire is of interest historically, because it is over this railroad that Henry David Thoreau and companions (as well as R.W. Emerson and many other Concord, Ma residents) used to reach their beloved Mt. Monadnock. Thoreau traveled the rails in 1952, 1858, and in 1860. And the Troy Depot, now a historical museum, is a delight. Call ahead for an appointment.
I didn't find anything about whether dogs were allowed or not anywhere online. I went to two different parking areas near Holden, where they very clearly state "NO DOGS ALLOWED." I was very disappointed, as this was the explicit reason for my trip - to bring my pooch with me!
Beautiful and well maintained trail. Quite flat and pretty environment.
Hi folks,
I read the reviews and went anyway. Started at the Hinsdale end on Northfield Road and went 10 miles. The trail starts on a private driveway directly across from the gas station. I truly enjoyed my ride. Yes it does have mixed surface conditions; abandoned buildings from some industrial past; and the horse-impacted stretch. But is also boasts spectacular river views, covered bridge worth seeing, and a nice trail bridge to ride over. Best of all, the reviews seem to have kept it quiet and underused.
The worst of it is at about mile 8 where the trail first crosses Old Westport Road and Old Spofford Road. There, the horses have torn up the trail and you go between jarring bumps and deeply worked lose sandy soil that will grab your wheel and bring you to an involuntary stop. These conditions last 1.5 miles or there abouts. I won't ride that stretch again; but such is life with multiuse trails.
After mile 10, I exited the trail on the second crossing of Old Westport Road and used the road to bypass the bike unfriendly portion for my return leg. The road is a pleasant spin through farm country.
Overall I found the trail low gradient, shaded, and with easy road crossings. It's not the place to set the land speed record on your road bike and I would not bring young children. But it is certainly teenager compatible and heck, I had 2 hours to kill near Brattleboro and this was just the ticket.
Ashuelot river trail north of West St Keene is short but scenic, today we did 15 miles round trip on southern part of Ashuelot river trail south of Keene. The trail is really nice for about 4-5 miles after that you follow the power lines and not the river and the going is not as smooth but OK with hybrid bike. We went as far as Swanzey Lake Rd which you can see from a brown house who's back yard is the trail and that is about 7.5 miles one way and it is mostly flat .
A well maintained, serene, lakeside, forested and gentle day on asphalt . This scenic ride through small towns was full of reminders of past manufacturing and local efforts to attract more riders of all ages. The Adams town visitor center was brand new.
Lots of benches and fewer picnic tables allowed for stops and lunch breaks.
A polite mix of strolling, riding families, couples, friends and single participants added to a soothing day of healthy exercise!
Nice 4 plus mile hike for someone 72. Friendly people on the trail and neat falls. Would consider it moderate.
My husband and I did this Trail on July 28th...was beautiful! We did it end to end, started at the Lanesborough parking lot then rode to Adams and back. It was perfect - with a lake to ride by, plenty of pull off benches, pond landscapes. My advice is to start in Adams and ride to/towards Lanesborough, there's a slight incline when you're entering Adams so if you want an easier finish ride towards Lanesborough. Trail is clean & well kept also.
Well maintained with beautiful scenery along almost the entire length. Lots of places to sit and rest or view the surroundings. A lot of this trail is dead level so its and easy ride. I parked at one of the two lots at the south end of the trail. Good starting point as there are toilet facilities there.
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