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 34 trails covering 536 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.
_155550_st.jpg)
_0_st.jpg)
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 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...
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...
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...
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...
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 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 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...
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 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 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 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...
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...
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 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 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 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...
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 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 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...
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,...
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...
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 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...
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...
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 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...
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 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 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...
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...
_155550_sc.jpg)
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 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...
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
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...
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...
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...
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...
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...
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 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 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 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...
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...
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 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 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...
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...
_0_sc.jpg)
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 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...
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...
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...
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,...
My son and I stopped to the Voorheesville trailhead which is considered the end of the trail. We biked from here to the start of the trail in what's considered Albany. This is a great trail. From the beginning in Albany to Voorheesville is slightly uphill going but the way back is more of downhill feel (this coming from my 12 year old son). He did say this is one of his favorite trails we've ever done! They have bikers tools and air pumps at the beginning of this trail which is cool. Lots to see also along this trail. Will definitely make the travel to do this trail again! As described it is 9 miles each way.
We startes in Amsterdam,we parked on a dirt section on Cleveland Ave,little further down is a bigger paved lot.We did a little detour on Bridge Rd,nice pedestrian bridge(flowers & a few interesting sculptures.) Rode into Riverlink Park. Small park,but a cute little detour. Most of the trail was paved,there was a section that was bumpy.Pretty flat. About 4-5 miles was crushed stone/dirt.If it rained heavy may get muddy.We enjoyed the trail,a few street crossings.Was a pretty quite trail on a sunday.Was a mix of shade & sun. We seen some wildlife,seen a fisher & what looked like a weasel,was so quick.,so that was cool!.We rode to Sparkers. There was a cooler of waters & there was bathrooms across the street.(Courtesy of the church)We rode about 44 miles there & back,with detour. The trail is broken up into sections,so we rode this section. Hope to ride the Buffalo section..
My daughter—an inexperienced biker—and I enjoyed the diverse landscape and beautiful views along the Connecticut River. However, because the trail was so overgrown and rough for the last mile or so, we didn’t make it to the end to see the historic bridge.
Tuesday July 09, 2019, 5:30 pm.
Weather 88' F, low humidity, very light clouds.
Great weather for riding this great trail. Massachusetts really sets the bar for bike trails. This one has a line down the middle to help the careless riders better their performance. There are benches near view spots with poems and examples of flora and fauna carved into boulders. There are granite mile markers on both poles and pavement stones at the side of the trail. The pavement was very smooth and there are only some slight inclines. Tunnels and bridges, a variety of scenery, this is both a community trail and a destination trail. I drove 2.5 hours for this one and the much shorter Canalside trail a half hour away in Turner Falls, doing both on the same day with a mid-trip visit to the Bridge of Flowers in Shelburne Falls. All 3 places worth the trip, but now I have to complete the other sections of the Mass Central Greenway. Good job Massachusetts!
Tuesday, July 09, 2019. Weather 88' F, few whisps of clouds, and low humidity.
It was a great weather for riding and a great trail to ride. The photos here are exactly what you see, except for the very nice park at the beginning of the trail. The village of Turner Falls is quite nice to visit also.
Only 15 minutes away in Shelburne Falls is the Bridge of Flowers, which is a beautiful short walk with a pub at one end. Combine these two activities into one great outing.
This trail was nice and flat. We got misdirected when we came to the main rd. The bike route follows straight across but we got confused as the sign said road closed, bridge out- but that was exactly where we needed to go. Then you turn to the right and follow thru old brick buildings that are mostly un-occupied. There is road crossings as others stated and they are marked. The cool trestle bridge was a nice view of the river. Past the bridge is a straight way then a few turns as you go slight uphill before it ends at the rail yard. There is a few picnic tables an benches along the entire bike route. Weather was good and cloudy also a nice breeze or it may have been hot along the open canal. We brought the kids to the amazing playground after. There is also a skate park too and you can fish as we saw ppl do- I assume state license needed; we were from CT.
We rode this trail in two sections both in the Rochester New York area. Our first mini trip was a 20 mile run between Brockport and Rochester New York and the next day another mini run between Brockport and Albion New York. This trail rocks. Great views along the canal, Very friendly people in the many towns along the way who welcome cyclist. Many accommodations along the trail as well. Our favorite towns were Brockport and Albion. These are old canal towns that have kept there history. The trail offers great views is hugging the canal and offers some shade however the areas we rode were mostly open sunny areas. I have traveled on many canal trails and this trail did not fail. The trail is well marked has a town every 4 to 6 miles.We will return to do the entire trail soon.
Beautiful scenery, good asphalt surface with big bumps well marked. Not much at the south end but great food and ale at the north end...plan accordingly. May also want to plan camping at Clarksburg State Park...about 15 minutes from the trail head. Met a few RTC members. So far for me, this is the best trail in Massachusetts. Please support - and a big thank you to - the Conservation Trust! Signed, one happy biker from New Hampshire.
Found this gem while visiting the Berkshire’s. Well maintained and a pleasure to ride. I went from Adams to Lanesborough. I appreciate the markings for the rises in the pavement (very few) due to roots coming up. Bravo Berkshire area for taking care of this one.
My group of 4 started a bike trip from downtown Buffalo. Our plan included stops in Lockport and Brockport. The “canalway” trail out of Buffalo had many closed sections without properly marked detours. We were forced to figure out our own detours with the help of other bikers. Signs are desperately needed that give bikers proper detour paths (all on the road). As we moved east out of Tonawanda the trail improved and there were few detours. However, the NY Canal Corp is currently working on sections of the trail. They are adding a sand gravel mix that is very difficult t for riding bikes. All 4 of us had close calls with falling
Great scenery along the entire route. We started at the south end and rode all the way to the north end and back.
Get Your 2018 RTC TrailNation Jersey!
Download the TrailLink mobile app and take TrailLink with you!
Donate and Get a FREE 2018 RTC Guidebook!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
