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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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 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...
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...
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 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...
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...
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...
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 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 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 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 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 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 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...
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 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 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...
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 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,...
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 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...
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 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 Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of January 2016, 87 miles of trail are built and scattered across the state....
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...
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...
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...
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 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...
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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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 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 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 Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of January 2016, 87 miles of trail are built and scattered across the state....
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 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 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...
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...
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...
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 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 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...
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...
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...
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 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...
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...
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 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...
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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...
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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...
Started in Fitzwilliam near MA border and road to Keene and back. Used a road bike with 25mm wheels. If you are comfortable riding dirt/gravel on a road bike the trail is quite easy to ride. Some sections were muddy despite not raining recently. I imagine those sections would be more technical after a rainstorm.
Rode this trail heading northwest from downtown Keene.This trail is fantastic when in the center of town. As soon as you cross Hurricane rd., however, the trail surface degrades, becoming sandy and eventually very rocky around the landfill, where we turned back. I was riding a gravel bike with 38 inch tires, but it's pretty clear that this trail is mountain bike only unless you want to walk your bike through a number of very rocky sections.
I started at the southern portion of the trail. I rode a gravel road / light touring bike (Specialized Sequoia) and it was fine but in hindsight I would have done a bit better with the FatBoy. There was a fair amount of sand in the first portion of the trail. I encountered some decent sized muddy sections but nothing crazy. The variety of scenery is great and the trail is very quiet. I encountered about 3 other bikes and a couple of people walking. I wouldn't do this trail if there's been significant rain in the past few days because of the pooling that I saw in some of the sections flanked by rock walls. And I rode in July and was flanked by large flies seemingly at all times. But given the challenge and scenery it's worth it!
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.
It is a little short at 1.4 miles but a nice trail. If you are a flat lander like me, the hills can be a little bit of a challenge but not bad.
I did this in the summer of 2018. as others have mentioned, quite rough in spots. quite wet in spots. and sandy, i hate sandy.
could be a nice trail but as it is, i wouldn't recommend it for bikes, even a mountain bike. also, beware of the dogs.
with the exception of the Northern Rail Trail, New Hampshire needs to step up their game regarding their rail trails.
The trail description in the intro is quite accurate. It's a little gem but rough around the edges. The river makes this route. If it wasn't there I certainly wouldn't bother. Forget a road bike. Hybrids should be OK but don't get too comfy. This trail's changing surface & overgrown vegetation will keep you engaged. I also wouldn't bring small children unless you don't mind walking long stretches where the grass gets so thick it makes for difficult pedaling. Don't bother going after a significant rain. This is a wet trail for sure. Make sure to bring your camera & start at Dole's junction on the southern end of the trail.
We started our ride at the Hannah Duston parking lot in Boscawen. The RTC map takes you to where the ride starts but not the parking area. The parking area is shortly after you get off I-93. It's a Park and Ride lot. There are good signs to indicate which way the ride starts. It starts 0.5 miles down the street. The first mile or so is out in the open. After that, it goes into a shaded area. At this time of year, the mosquitoes are plentiful and ready to bite. The surface of the trail is crushed gravel and easily ridden with a hybrid or mountain bike. Sadly, we had to cut our ride short after about 5 miles due to a bike malfunction. We plan to go back and give it another try. An additional point of interest is the monument to Hannah Duston, which is located to the left of the trailhead kiosk, across a little bridge. It sits on the banks of the Merrimack River.
Overall it was pretty good. Not something i would take a bicycle on, very uneven narrow trails. However it is an enjoyable walk which can be traversed by almost anyone.
Rode from the start near Keene ice north to Hwy 12. All paved until you cross Rt. 9 where it turns to hardpack. nice ride through golf course. Gets a bit rough north of Hurricane road. eventually started dropping to singletrack in places; just past huge former landfill just before Hwy 12 it got too wet to continue (early May). Gentle ~1% grade. This ride was good on my gravel bike. Mountain would be ideal but not necessary. Saw a few on fat bikes- overkill, but do not know whats north of 12. Moderate use on a Saturday afternoon closer to the city, including one horse.
The first section of the Mascoma River Greenway - which was a section of the Northern Railroad - open in 2018 from High St. in downtown Lebanon westerly two miles to Glen Rd. in West Lebanon. Surface is 12-foot wide pavement. The MRG is not a continuation of the Northern Rail Trail, but the distance between on local streets is very short.
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