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 36 trails covering 314 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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Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
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 Village Spur Rail Trail begins in downtown Belmont, and stretches from behind the Belmont Mill to the Tioga River on the west side of South Road. Out and back for the entire trail is about four...
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 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 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 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...
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...
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 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...
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...
The 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...
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 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 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 Merrimack River Greenway Trail (MRGT) will stretch from Boscawen southward through Concord to Pembroke, offering scenic views of the Merrimack River, the city and the surrounding landscapes. The...
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 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...
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...
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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
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 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 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 Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...
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 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...
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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...
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...
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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 Merrimack River Greenway Trail (MRGT) will stretch from Boscawen southward through Concord to Pembroke, offering scenic views of the Merrimack River, the city and the surrounding landscapes. The...
The Village Spur Rail Trail begins in downtown Belmont, and stretches from behind the Belmont Mill to the Tioga River on the west side of South Road. Out and back for the entire trail is about four...
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...
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...
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 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...
The 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...
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 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 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 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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
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 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 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 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 Merrimack River Greenway Trail (MRGT) will stretch from Boscawen southward through Concord to Pembroke, offering scenic views of the Merrimack River, the city and the surrounding landscapes. 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...
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 Village Spur Rail Trail begins in downtown Belmont, and stretches from behind the Belmont Mill to the Tioga River on the west side of South Road. Out and back for the entire trail is about four...
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...
The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...
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...
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...
Last minute choice…what a beautiful ride…groomed path in nice condition…highly recommend.
Fifty nine mile long well maintained trail that provides a nice mix of scenery the entire length.
We parked in Keen at the Cheshire Trail Parking spot and went north to Walpole. Nice trail, unpaved but well-packed earth and shade. We have 2 electric bikes, so 2 steep inclines were not a problem. Unfortunately, after about 10 minutes we run into a closed section. Not sure when it will reopen - we saw no signs of work. We turned and went south to Keene, and in the center of Keene we followed signs for a bike trail which led us to Ashuelot River trail. It has several pretty bridges over roads, about a mile of paved section, and once it leaves Keene it is unpaved, but still has good surface and shade.
In Keene you can also go to southern section of Cheshire rail trail, but it is not easy to find, so use Google Maps on your phone to be sure.
Sections of the trail are badly wash boarded, enough to almost knock you off your seat. Every quarter- to half-mile there's a metal gate across most of the trail, with a narrow passage to the side. The surface of the passage is large gravel, usually combined with deep ruts. Parts of the trail are reasonably graded; it seemed that most are too rocky for smooth riding. We rode from Littleton to Lisbon, 20 miles round-trip. It felt like 50. Having said all that, if you're up for the beating, it's a pretty ride, lots of shade, some nice river views.
Probably a pretty good ATV trail. We saw a lot more of them than bikes. (20+ ATVs, 3 bikes) Lots of large gravel. Sandy in other places. Lots of washboard surface from ATV tires.
Parked at the old train depot in Troy and rode South to the end at the Mass border and back. The trail is not paved, not groomed but that’s part of what makes it fun. Riding through the woods, along a stream, crossing a wetlands with high bush blueberry bushes loaded with fruit and on the way back jumping in a clear water pond to cool off, with a view of Monadnock …perfect day! Oh, and we saw one runner and two people picking those berries…a very memorable and delightful day on the trail.
Dirt trail 90%, but there are quiet rural roads paralleling it if it seems too rough in places and the countryside is amazing through Swanzey! The ride out of downtown Keene is very interesting for a few miles as it follows the power lines which have wooden piers(?) under them for maintenance that they were building as I traveled, there is a neat overpass of the highway, but take great care at road crossings as they are unfortunately on sharp curves with nary even a crosswalk painted! Loved this ride.
We were pleasantly surprised with how nice this trail is based on some of the reviews. We ride hybrid bikes with shocks and comfort seats and are accustomed to riding gravel and backroads so this trail was just what we look for. Trail is firm packed gravel and very smooth, no potholes or washboard experienced on our ride. Plenty of parking available on the Castleton end of the trail, we parked in the trailhead lot across from the Amtrak station. Definitely in our top 10 list of VT rides.
Carleton to Poultney section somewhat better but still rough due to horse traffic.
We parked in the Trestle View Park in Franklin (dodging the sprinklers uselessly watering mid day) and went all the way to the beginning of Tilton. There was a parking lot and a small skate park. There were also a trail directions sign with pictures on how to work your way through Tilton to the other end of the trail. Plus a link to the directions online. We decided not to bother and turned around and headed back to Franklin. I checked online maps and this spot is labeled as Winnipesaukee River Trail Northfield. If we went back and had a sprinkler issue or no parking then we'd head over to this other parking area. The Franklin end of the trail, after the initial slow uphill grade, is wide and flat and we ran into walkers, dogs and people with strollers.
Wife and I started in Hanover and went 15 miles the turned around and came back. Beautiful streams and lake on the way. Trail wasn’t crowded on this Thursday.
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