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....
The Albany County Helderberg-Hudson Rail Trail offers a paved, 9-mile route following the former Delaware & Hudson (D&H) Railroad, later the Canadian Pacific Railway, which stopped using the corridor...
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....
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...
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 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 40 miles from Boston to Northampton...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...
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...
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 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...
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...
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...
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...
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...
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...
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...
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...
When complete, 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,...
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 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...
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 40 miles from Boston to Northampton...
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...
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...
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...
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...
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...
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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...
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
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...
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...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...
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...
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...
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 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...
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...
When complete, 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,...
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...
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...
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...
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...
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...
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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...
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 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....
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...
When complete, 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,...
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....
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...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...
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...
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 40 miles from Boston to Northampton...
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...
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 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...
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...
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...
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...
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...
The Albany County Helderberg-Hudson Rail Trail offers a paved, 9-mile route following the former Delaware & Hudson (D&H) Railroad, later the Canadian Pacific Railway, which stopped using the corridor...
The trail is in good condition, flat, clean, and scenic. It checked all the boxes.
About 5 miles of newly paved trail has been open east of Amsterdam to Pattersonville. It is a really nice ride along the river.
The trail has been ruined since they've paved it. I use to see different kinds of wildlife like, snapping turtles, timber doodle. Now nothing they're all hiding. Totally ruined the nature aspect of the bog.😔 won't go back
Nice trail, crusher run, so you have some rough spots. Overall a nice short trail to get your bike out or take a walk. I probably take a fishing pole with me next time on the trail. There are stations to do cardio or other exercises along the trail.
This trail is not at all as described. It started off on crushed gravel for a few hundred yards. As soon as it entered the woods it became a foot path of a nearly contiguous stretch of single-track biking with (occasionally without) large roots and rocks to navigate. We walked our bikes more than we rode them and went a half mile without getting to the reservoir before finally turning around.
I started the trail in Hinsdale, and found it reasonably rideable (I use a Specialized hybrid) through Winchester and a few miles beyond. However, the trail started to get rougher including some wet areas. I came to a spot where it followed high tension lines and by the time I got to the monadnock speedway, I was done. I went back to Winchester via Rt 10 and then caught the trail back to my car. Not my favorite trail, but if you have the bike and the inclination, it could be fun for you
We started the trail in Keene. The first 5 miles were nice, but we had to dodge pretty deep chipmunk holes. The trail is very poorly marked and we missed seeing the Sawyer Crossing Covered bridge which could not be seen by the trail. After 7.5 miles we got turned around by heavy mud, water and a downed tree. I would say this trail might be perfect for equestrians and aggressive mountain bikers.
19.5 mile round trip from Platt St Glens Falls NY to Lake George and back. Enjoyed lunch and a boat show in Lake George at the 1/2 point which added to the charm and makes the few larger hills coming out of Lake George worth while. Near the Glens Falls end has a nice top for a drink The trail is all asphalt. A short section is on the road (rt 66 and 17) with decent shoulder. The northern section from Glen Lake to Lake George is nicer than the southern section but it is a bit hilly at times. The southern section has a lot of road crossings causing it to be stop and go.
I tried to access this trail from the northern end which proved impossible. There is no road access until you get to parking areas on either end of the causeway. The trail is not marked with any signage at those places, either, but the track is evident when you cross into the fishing access parking areas off Rt 119. As mentioned, the trail is muddy and filled with puddles during this rainy August, and several trees across the trail. I was not able to reach the northern end because of a very large, multi-branched tree across the trail about a mile south of there. But it was pleasant riding close to the Connecticut River and there were almost no other people on the trail on a weekday.
We rode part of this trail while doing some single track riding on the Crosstown trails in West Dover, which connects with this trail. This is not a family friendly paved trail which is the impression I had from the description. I am glad I didn't plan to ride it from Dover to Wilmington with my 9 year old. The part of the trail we saw was single track comparable to a hiking trail. It is not wide, not flat, and not smooth. It is narrow, windy, and filled with rocks and roots. It is not appropriate for little kids or bike trailers.
The Crosstown trails in this area are wide gravel paths. Great for kids who can make it up a decent hill. The single track in the area is nice. It needs some trail maintenance and reroutes along with clearing and trimming. Some areas are nice to ride, others are a mess of roots which are difficult. The trails on the map were very well mapped. It was a nice find on a trip to the area, we will be back!
NOT ASPHALT! Only one small section (1.5 miles) in Dover is paved... ended up biking Rt100 from Wilmington to Mt. Snow, not much of a shoulder but not much traffic and pretty flat.. nice scenery!
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