Explore the best rated trails in Bennington, VT. Whether you're looking for an easy walking trail or a bike trail like the Spring Run Trail and Appel Way Trail. With more than 36 trails covering 538 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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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 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...
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...
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 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 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...
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 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...
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 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...
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...
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,...
Popular with residents of Saratoga County who commute under their own power or love to exercise outdoors, the nearly 9-mile Zim Smith Mid-County Trail is considered the backbone of a growing trail...
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 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 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 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...
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...
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...
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 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...
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...
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,...
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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...
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 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...
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 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...
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 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...
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...
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...
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 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 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 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 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 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...
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 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...
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...
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 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 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...
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 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,...
Popular with residents of Saratoga County who commute under their own power or love to exercise outdoors, the nearly 9-mile Zim Smith Mid-County Trail is considered the backbone of a growing trail...
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 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 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 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...
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 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...
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 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 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...
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...
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 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...
I just went to Black Jack Crossing road. There is no parking. Where is someone parking a horse trailer to get on this side of the trail?
So happy we found this trail! It’s beautifully paved and nearly all flat. There is a gradual downgrade for the last few miles into Adams ... which means an upgrade on the way back. ¿ We live in northern CT so it takes us about 1.5 hrs to get to the southern Trail Head ... but it’s worth the drive. We’ve ridden this trail twice this year and will be back next year!
We did this trail Columbus day weekend, the weather was perfect, the views spectacular and it wasnt very crowded at all. Will definitely do this trail again!
This is a lovely trail. We ride it to connect to the Champlain canal trail in waterford. The connection is on waterford streets, but very easy to negotiate, just look for the Empire State Trail signs and enjoy the empty gravel tail along the canal
Absolutely beautiful trail! I went on October 10, 2020. A warm sunny day, lots of bikers, walkers, And in-line skaters. The trail itself is so smooth - not one pothole. And lovely views along the lake and quieter views of the wetlands. Will definitely go again next year and highly recommend it.
The newly refurbished Ashuwillticook opens Friday Oct. 9 @ 3pm
From Coons Crossing the trail has been extended 2.5 miles to Mechanicville. Beautiful broad paved trail along the railroad but far enough away to be safe. You may see a freight during your trip.
Trail has beautiful scenery, paved, flat, plenty parking at Berkshire Mall just go, you’ll be glad you did. Ate at Pizza House in Adams, food was great just 1 minute off the trail.
Great trail in the Albany area! Can't really add to the previous comments. Just note that there is major road construction on Rte 32/ South Pearl St at the eastern end trail head. The parking lot is still open but you may experience delays in getting to it. I would definitely advise not trying to on-road cycle to the trail head.
Wonderful trail. Nine miles of crushed stone and hard pack dirt from southern end to Castleton University parking lot. I would not use a thin tire road bike. Beware: the southern end is a dead end 2 miles from Poultney and does not have a parking lot as indicated on the trail map. You must park in Poultney in a well marked lot off of Bentley Ave.
We started in Walpole at Blackjack Crossing. First few miles were tough! But the remaining 12 miles into Keene were great. Some great views and remnants of the railroad. Some beautiful cuts in the stone. Highly recommend!
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