Explore the best rated trails in Windsor, VT. Whether you're looking for an easy walking trail or a bike trail like the South Barre Bike Path and Stevens Rail Trail. With more than 32 trails covering 291 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 Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
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...
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...
Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...
The Millstone Hill West Bike Path connects the charming communities of Graniteville and Websterville in central Vermont. The trail is part of the Central Vermont Path, a proposed trail network to...
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...
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 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 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 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 South Barre Bike Path is a paved trail approximately 1 mile long, running from Bridge Street in south Barre to Fairview Street in Barre City. The path passes the Barre City Elementary and Middle...
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 Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
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 Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
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...
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 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 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,...
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...
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 Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...
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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...
Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...
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 Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...
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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 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...
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,...
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...
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...
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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
The South Barre Bike Path is a paved trail approximately 1 mile long, running from Bridge Street in south Barre to Fairview Street in Barre City. The path passes the Barre City Elementary and Middle...
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
The South Barre Bike Path is a paved trail approximately 1 mile long, running from Bridge Street in south Barre to Fairview Street in Barre City. The path passes the Barre City Elementary and Middle...
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...
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...
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 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...
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 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 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 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...
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...
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Locals lovingly describe the Cross Vermont Trail as a patchwork quilt that will ultimately form a 90-mile trail from Lake Champlain in the west to the Connecticut River in the east. A component of 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 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...
he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
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 Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
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 Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...
It is evident that much work has been done to improve this Trail.
Still I see from a optical sense there may be some improvements made to beautify it. Cut brush from the rescue could be chipped. Small dead saplings and other dead wood that is growing in the original rail-bed footprint could be removed and chipped lending to a more serene authentic scene of the rail-bed.
At the end if the trail on Jaquith road nearest to rt. 137 Prior to the trestle is a very steep rise in the rail bed not easily climbed by vintage locomotive engines in my view I imagine a wooden ramped structure bringing this higher part of the rail-bed up to the top of the trestle.
I wonder if there are any old photos of this elevation transition and how it was accomplished. These pictures may be a nice touch to this section's bulletin board
All the trail is delightful and the 100 yr .old steel span bridge is a great undertaking. We loved the red Lobelia in full Bloom Aug. 2 into it's brook beneath. I love the Old R.R. ties left in place to give more of a R.R. feeling . The bench at the swamp in the first section is a nice touch.
All in all a high five rating despite I feel a bit more cosmetic work can greatly improve the feel of this great noble R.R.route
Rick Beausoleil Greenville NH.
Having ridden this trail in sections numerous times, and having ridden the entire length in a day last fall, It's my opinion that this is the finest rail trail for cycling purposes in NH.
In Merrimack county (Boscawen to Danbury) the dedication of the local friends group is evident. The trail is well maintained and the surface is excellent. From Grafton to Lebanon (Grafton county) the surface is trickier, with regular sandy spots and some exposed railroad ties. Despite this, the trail is still very ride-able in a gravel bike, and my wife had no issues in Merrimack county on a cruiser/townie bike.
started at the southern terminus at rte 63 North of Northfield Mass. and South of Hinsdale. The trail starts across rte 63 from the large parking lot, up on the berm. The trail is in poor condition at this point. The trail is not much more than a unused fire road. A better starting point would be the Hinsdale rail station. My highlight was the Ashuelot Covered Bridge. I returned to my car from that point.
We rode much of the trail on a tour from the MA/NH line area north of Winchendon, MA to Keene, NH. It's a beautiful, relatively flat route with some great views though high water source areas, ponds and some views of Mt Manodnock then descends along the river into Keene. We were on semi-loaded touring bikes, so jumped off on roads when they paralleled the trail since the surface is a little bumpy. Hybrid or MTB's (as recommend) would be more comfortable, but for those on touring bikes, the direct route through some road less areas is well worth it.
The trail was an easy and serene bike ride, we enjoyed it very much. Definitely recommend if you are in the area.
First of all, Peterborough is a lovely little town to bike in and around. The trail was shaded, clean and paved all but 1 mile or maybe a little more. We parked in the shopping center parking lot and then followed the well marked signs along some town roads before getting on the bike path. Beyond the parking lot on the north end, the cinder path continues. We bikes for a while before deciding to turn around.
Nice shady trail along the River. Loved the sound of the river along the trail. We stopped at the train depot in Tilton. It does continue but, looks like your in the street.
This trail is closed now summer/2020 but it has a detour. It’s basically riding the back roads all the way to Walmart, and Shaw’s where you can go on another trail. That trail is not suitable for wide UTVs because of the metal posts.
I have a Polaris ranger crew and it can’t really use this trail because of the metal posts. It’s a pain to try to get through.
The trail starting in Lisbon is not a bike riding trail. We have fat tire e bikes and road three miles toward Bath NH. The trail is very rough with large crushed rock. The trail is for ATV and dirt bikes in the summer and snowmobiles in the winter.
A beautiful trail along the Sugar River, with some gorgeous covered bridges, which my wife and I much enjoyed. The ATV users were generally polite. But note: (1) Some parts of the trail have very, very sandy soil. My wife, an accomplished RAGBRAI rider, had to portage her Diverge, with 35mm tires, at one point, as did I coming back, riding a Warbird with 40mm Maxxis Ramblers. (2) The ATVs kick up great amounts of dust, so be prepared. (3) The entire trail is slightly downhill from Newport to Claremont, as the Sugar flows to the Connecticut. (4) Unless you ride at a decent pace, you may have bug problems.
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