Explore the best rated trails in Bennington, VT. Whether you're looking for an easy walking trail or a bike trail like the Zim Smith Mid-County Trail and Spring Run Trail. With more than 37 trails covering 575 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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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,...
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 Albany-Hudson Electric Trail (AHET) follows a 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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...
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 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...
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 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...
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...
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 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...
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...
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 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 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...
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...
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 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...
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...
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 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...
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...
The Albany-Hudson Electric Trail (AHET) follows a 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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,...
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 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 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 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,...
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...
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...
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...
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 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 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...
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...
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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...
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...
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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...
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 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...
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...
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 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...
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...
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 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 State Route...
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...
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...
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...
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...
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...
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...
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 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...
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 Albany-Hudson Electric Trail (AHET) follows a 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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 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...
My wife and I tried this trail because it is a fairly short drive to Hoosick Falls. It is NOT your typical bike trail. It is gravel (hard packed crushed stone) but not difficult to ride on. We parked in a lot in town at the middle of the trail, rode north which was very nice and not too long. The north end is a bit desolate. We rode back and attempted to continue on the southern part, however it was not marked at all and we could not find any visible "access" point. We eventually made our way through the town and found a sign pointing us toward the trail.
This eventually brought us to the southern end of the trail near some little league ball fields. We rode northward again on gravel for about a mile when the gravel abruptly stopped. We spent 5 or 10 minutes contemplating whether to continue or not. Ahead of us was just grass, but not something that looked like a trail. After about 100 yards it became a mowed grass path which was definitely an old railroad bed, rather high with the river to our left and a ditch to our right. To say the least , it was NOT what we expected. This section was directly behind peoples homes and we were not even sure if we were on a trail at this point. It eventually went under a train bridge and came out where it was not marked at all, a few blocks from where our car was parked. To say the least, we wish we had read a review similar to this so we would have known what to expect. Hopefully this will help to inform someone else in the future.
Once we got to the Sanitation site north of Keene the trail wasn't more then a goat trail. Muddy, rocky narrow, and not very much fun. We turned around. Maybe it would be better from Walpole south.
Nice flat path for a run. Definitely not 3.5 miles as stated. It’s approximately 3.25 according to my Garmin.
I live about 7 miles from the South Londonderry trail head and only wish the trail was better suited for my hybrid bike. The first 3 miles (approx) to the Winhall campground are in bad shape (dirt festooned with rocks, roots, ruts and mud puddles). I don't know when the article summary was written, but I have a different idea of what "well maintained" means. Those with mountain bikes or fat tire bikes should have a much easier time with it though.
The trail ride is sandwiched by a campground road for a couple of miles. It's asphalt, and other than navigating several speed bumps, is an easy ride to another dirt path on the Jamaica side. It's in better shape than the South Londonderry portion. It's not in great shape for riding either but very manageable.
The two dirt path portions follow the contour of the tree lined West River. The view is particularly vivid, particularly in Autumn, and a favorite spot to hike with my dog. As a bike trail though, it needs work.
This was a bike ride from Depot Street in Hinsdale to Keene State College area. Beautiful views of Ashuelot River along ride and several covered bridges. Several old mill buildings in various state of disrepair to look at. The trail from Depot Street to near Riverside Lane in Swansey has good sections of loose gravel with several sections of puddles and mud. This part of the trail is good for mountain bikes and for those that don't mind going through puddles that vary in length from a few feet to over 20 feet long. Some are deep too. A few potholes and gopher holes in this section and one bridge with bad decking boards. I'd rate this first section of the ride a 2. From Riverside Lane up to Keene trail is wide with good gravel base. Easy for most bikes to navigate this. I'd rate this section a 4.
2021: Biked the Erie Canal trail from Buffalo to Cohoes. Well worth the time. And mostly a very pleasant experience, with just a few caveats. Trail improvements are ongoing and signage along the trail is not always up to date, so check your route carefully, especially where it is on-road. The initial section from downtown Buffalo is grungy city streets, but that improves with a great, mostly off-road trail all the way to Lyons. Lockport to Spencerport is fairly exposed, but from there on to Lyons is generally pleasantly green and shaded. From Clyde to Port Byron and through Syracuse were onroad and not always clearly signed and were the least pleasant. From the east side of Syracuse all the way to Cohoes was a delightful and beautiful ride, with the exception of finding one's way onroad and with poor signage through Rome. All in all (despite my caveats) a good, local, human-powered bucket-list endeavor, with thanks to all the communities along the way and everyone maintaining and improving and filling the gaps in the trail.
This trail is a lot of fun! Mountain bike is the best! Lots of railroad stuff to see!!!
I’ve done the rail trail from North Chatham all the way to downtown Hudson. If you park in North Chatham off Depot Road /203 intersection it’s very picturesque. You go south down through beautiful horse farms and streams. You come to the village of Valatie near Bagel Tyme. There is also another parking right off route 9H. It is very accessible, follow the signs through Kinderhook and pass Samascot orchards. You will see a working cow farm where you cross route 9. Use the stop light button! You’ll cross through a street line with corn stalks. You come to the historic Stuyvesant Falls overlook where you will see a beautiful waterfall and an historic textile mill. textile mill.were you were see the remains of all textile mills
I set out to ride the Albany Hudson electric trail by first parking my car at the Rensselaer train station, and taking the train to Hudson. I wish I had never done so.
I made it about three or 4 miles on the trail, onto the first part of the trail that is built underneath the electric wires following the route of the old trolley. Unfortunately, the trail itself has a large divider installed on it as that first segment of off-road trail gets routed onto a street. It's about 6 inches high, and it's in a place that is absolutely critical for a rider; you need to look up to check traffic, not down to see an idiotic 6-inch- high divider on the trail itself. I hit the curb and went flying. Fortunately I only broke my left wrist.
I have never, in riding hundreds of rail trails, seen one that had a large divider placed in the rail trail itself. Perhaps they put this here to prevent cars from driving down the trail. It's a deadly hazard and it needs to be removed.
I have hiked and rode horseback on the Cheshire rail trail needs to be welcome signs for hose trailers somewhere!
Really nice trail! Very much enjoyed the ride. Would highly recommend
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