Find the top rated trails in Brattleboro, 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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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 North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
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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....
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal 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 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 Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
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 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...
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...
Mile 0.0 - DPW Garage Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
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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...
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 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...
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...
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...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
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....
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 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 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...
The Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...
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...
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
The year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
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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...
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
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 Mason Railroad Trail runs for nearly 7 miles from near the New HampshireMassachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
The New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...
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 Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
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,...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
Visitors to the Sugar River Trail (also known as the Sugar River Recreational Rail Trail) can be forgiven if they lose track of which side of the river they’re traveling. The 9.5-mile trail crosses...
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....
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...
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
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 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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
The Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...
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...
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 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 Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
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...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
The year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
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...
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 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 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...
This trail seems little-used. Rode a gravel bike starting at the parking lot at the south end. Several trees down in the trail and some puddles and running water (to be fair, it had rained the night before). The trail surface varies and while it’s manageable, this isn’t a trail for someone looking for a leisurely rail trail cruise. Nice views of the Connecticut River.
The entry leads you to believe there is a 9 mile asphalt trail linking two towns in a Vermont valley with just a small gap near the north end. Unfortunately, there is no such thing. The trail is a very confusing series of blue signs which go through the woods on dirt (mud) tracks, over grass lawns with no identifiable trail, and on busy and narrow town roads (the only asphalt on the trail). Talking to locals, we discovered that parts of the trail are used for mountain biking, but that the idea of a continuous trail linking West Dover and Wilmington is a dream that has yet to be realized.
My wife and I rode this trail from one end to the other. The scenery was beautiful, the ride was easy and the people were nice. Lots of lake views. Some hills but not difficult. Parking was a small challenge but not impossible. I would do it again in a minute.
Hi Guys!
I started this ride at the Hinsdale trail-head. Big mistake! The trail is poor and the vegetation is overgrown. It had to be over 2 feet high. There is a very small area to ride that's about a foot wide. Otherwise, it's very hard to ride and stay out of the vegetation. It was also very, very buggy for some reason. I know it's summer and bugs are out there, but it was unusually buggy. I used a lot of bug spray, but it didn't matter. The little suckers wanted me and got me. It is a very pretty area of the state, but I wouldn't go back until the fall, or maybe starting from the northern start point. I'm new to biking and can not do the whole length of this trail yet.
Yup. August 2017, hot summer day.
Riding along the lakes or reservoirs, it is nice and flat, paved well. A good trip.
The trail definitely has some potential if there was more participation from landowners, some of whom appear to be quite hostile to the idea. It appears that the trail did or attempted to cross through private land on the Townsend section northward towards a connection with the Jamaica section but you soon run into a labyrinth of blocked trail and more No Trespassing and Posted signs than I have ever seen in one spot anywhere in my life. They did dissuade me that day and I turned around which is most unfortunate. Laws being what they are in Vermont, there is nothing illegal about this of course. In many states, including Texas surprisingly there is a law against closing off a certain amount of shoreline areas to passersby and swimmers etc. in order to promote this activity which is ultimately beneficial to all, locals and visitors alike.
We took the scouts from Rte 140 (just past Stone St) north to the end by the Winchendon YMCA - 13.9 miles round trip - this was our first time ever on this trail, though we drive past it all the time on the way to camp.
Mostly paved, the short unpaved stretch added to the "Wicked Coolness" for the kids/adults with mountain-bike-type tires. The dad with skinny tires rode around on Old Gahdnah Rd.
There's a tire pump setup alongside the path about 1/4 mile in. Another awesome surprise was the little dirt path that leads to the back of Little Anthony's for Ice Cream &Clam Chowdah!
ps bring bug spray!
Don't bother with the trailhead behind the restaurant in Greenville (currently the King House) marked on the map---it's a dead end about 1/4 to 1/2 mile in. Someone has piled Jersey Barriers, concrete blocks and old storm drains to block the trail behind Pilgrim Plastic. That and the numerous NO TRESPASSING signs make it pretty clear that they don't want people hiking, biking or anything else up there.
Start from Adams Hill Road where it crosses the trail, it's a nice hike from there. There isn't a lot of parking available there, but I've never seen it too crowded. The day we went we didn't see anyone on the trail and once we got away from the road noise of Rte. 31 it was birdsong and peepers to accompany our hike.
One other thing---bring bug spray! We were swarmed by mosquito's and blackflies for most of the hike. I was glad I wore a long sleeve shirt and long hiking pants, so all I had to defend was my head and neck (yes, I forgot bug spray!)
Clear sunny day in May. Excellent conditions with sunshine and a gentle breeze to keep away the bugs. No ticks encountered. Walked 3.5 miles from the Blackjack Crossing trailhead.
Trail is in great shape although the first .25 mile (going north to the very end from the parking area at the end of Blackjack Crossing) is overgrown and a bit muddy. The first .25 mile stretch going south is the same, but then the surface is very good with crushed rock. There are muddy spots as you pass through the deep cut areas, but other wise, excellent. We walked but mountain bikes would fare very well. Road bikes NOT recommended.
Great trail but not for younger children around Goffstown part of the trail. Hope they can add railings to the trail near the lake as there is around a 30 foot drop in several areas.
When I rode it in September 2016, it stopped a short way into the town of New Lebanon, dead-ending before it reached the village. It's a nice ride as far as it goes. Hopefully it's now as long as the map says it is.
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