Windsor, VT Running Trails and Maps

433 Reviews

Looking for the best Running trails around Windsor?

Find the top rated running trails in Windsor, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
41 Results
Activities
Length
Surfaces
Type

Harrisville Rail Trail

1.6 mi
State: NH
Dirt

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Lake Winnisquam Scenic Trail

1.8 mi
State: NH
Asphalt

Mascoma River Greenway

2.78 mi
State: NH
Asphalt, Gravel

Millstone Hill West Bike Path

2.4 mi
State: VT
Asphalt, Ballast

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

Northern Rail Trail

57.8 mi
State: NH
Cinder, Crushed Stone

Old Railroad Trail

2.7 mi
State: NH
Dirt

West River Trail

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Ashuelot Recreational Rail Trail

21.5 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Blackmount Rail Trail

5 mi
State: NH
Cinder, Gravel, Woodchips

Bobby Woodman Rail Trail

1.7 mi
State: NH
Dirt, Gravel

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

Concord-Lake Sunapee Rail Trail

5.65 mi
State: NH
Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Cross Vermont Trail (Montpelier & Wells River Trail)

22.9 mi
State: VT
Ballast, Dirt, Gravel, Sand

Delaware and Hudson Rail-Trail

25.8 mi
State: NY, VT
Asphalt, Cinder, Dirt, Grass, Gravel

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

New Boston Rail Trail

3.9 mi
State: NH
Dirt
Accordion

Stevens Rail Trail

1.65 mi
State: NH
Crushed Stone, Gravel

Sugar River Trail

9.5 mi
State: NH
Ballast, Gravel, Sand

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

WOW Trail

2.7 mi
State: NH
Asphalt

Winnipesaukee River Trail

5.1 mi
State: NH
Asphalt, Crushed Stone, Dirt, Gravel

Ammonoosuc Rail Trail

23.46 mi
State: NH
Ballast, Dirt, Gravel, Sand

Cross Vermont Trail

87.4 mi
State: VT
Asphalt, Concrete, Crushed Stone, Dirt, Grass, Gravel

Hillsborough Recreational Rail Trail

7.8 mi
State: NH
Crushed Stone, Dirt

South Barre Bike Path

1 mi
State: VT
Asphalt

Appel Way Trail

1.3 mi
State: NH
Asphalt

Valley Trail

9.1 mi
State: VT
Asphalt, Dirt, Gravel

Village Spur Rail Trail

2.1 mi
State: NH
Asphalt, Dirt, Grass

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Henniker & Hopkinton Rail Trails

6.7 mi
State: NH
Dirt, Grass, Gravel, Sand

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Laverack Nature Trail at Hawkins Brook

0.6 mi
State: NH
Boardwalk, Crushed Stone

Merrimack River Greenway Trail

0.33 mi
State: NH
Asphalt

Warner Rail Trail and Bagley Rail Trail

1 mi
State: NH
Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
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...
NH 1.6 mi Dirt
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...
NH 0.9 mi Crushed Stone
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...
NH 1.8 mi Asphalt
The Mascoma River Greenway is a planned 4-mile rail-trail through the heart of Lebanon. The paved, multiuse trail is currently 2.78 miles, offering a pleasant opportunity for both recreation and...
NH 2.78 mi Asphalt, Gravel
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...
VT 2.4 mi Asphalt, Ballast
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...
NH 7.5 mi Asphalt, Gravel
Overview Spanning nearly 58 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...
NH 57.8 mi Cinder, Crushed Stone
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...
NH 2.7 mi Dirt
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...
VT 16.1 mi Asphalt, Dirt, Gravel, Sand
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
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...
NH 5 mi Cinder, Gravel, Woodchips
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,...
NH 1.7 mi Dirt, Gravel
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...
NH 32.9 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
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...
NH 5.5 mi Asphalt, Crushed Stone
Following the historic Concord-Claremont Railroad corridor, the Concord–Lake Sunapee Rail Trail will eventually connect communities from Concord to the southern point of Lake Sunapee via a multiuse...
NH 5.65 mi Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel
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...
VT 22.9 mi Ballast, Dirt, Gravel, Sand
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...
NY, VT 25.8 mi Asphalt, Cinder, Dirt, Grass, Gravel
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...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
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...
VT 2.2 mi Gravel
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,...
NH 3.9 mi Dirt
Accordion
The Stevens Rail Trail is part of the Concord-Lake Sunapee Rail Trail, which follows the historic Concord-Claremont Railroad corridor. Located about a dozen miles west of Concord, the Stevens Rail...
NH 1.65 mi Crushed Stone, Gravel
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...
NH 9.5 mi Ballast, Gravel, Sand
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...
VT 3.2 mi Asphalt
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...
NH 2.7 mi Asphalt
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...
NH 10.8 mi Dirt
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...
NH 5.1 mi Asphalt, Crushed Stone, Dirt, Gravel
Overview The Ammonoosuc Rail Trail carries its users for 23.46 miles along the scenic river that shares the trail's name. The river itself is a destination for fishing, kayaking, and canoeing. The...
NH 23.46 mi Ballast, Dirt, Gravel, Sand
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....
VT 87.4 mi Asphalt, Concrete, Crushed Stone, Dirt, Grass, Gravel
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...
NH 7.8 mi Crushed Stone, Dirt
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...
VT 2.3 mi Dirt
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...
VT 1 mi Asphalt
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...
NH 1.3 mi Asphalt
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...
VT 9.1 mi Asphalt, Dirt, Gravel
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...
NH 2.1 mi Asphalt, Dirt, Grass
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...
VT 18.1 mi Dirt
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...
VT 0.5 mi Gravel
The Henniker Rail Trail is an unpaved single-track path that follows a former rail corridor for 2.3 miles. The rail-trail picks up east of the former passenger station. Situated south of the Town of...
NH 6.7 mi Dirt, Grass, Gravel, Sand
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...
NH 1 mi Asphalt
The Laverack Nature Trail at Hawkins Brook is an ADA compliant nature trail that offers views of wetlands, forests, and wildlife. Located in the Town of Meredith, this trail connects the village...
NH 0.6 mi Boardwalk, Crushed Stone
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...
NH 0.33 mi Asphalt
The Warner Rail Trail and the Bagley Field Rail Trail are part of the Concord-Lake Sunapee Rail Trail, an eventual 34-mile rail-trail connecting Lake Sunapee and Concord, New Hampshire's state...
NH 1 mi Crushed Stone, Gravel

Recent Trail Reviews

Sugar River Trail

amazing Trail

April, 2024 by nariipr

We had a great time on this trail, which was easy to navigate. It was our first outing this season since we acquired an ATV for my wife and we enjoyed spending time together while exploring nature. We encountered people walking their dogs and bikers along the way. The trail was well-maintained and clean. We made sure to slow down and say hello to everyone we met. We will definitely be back on this trail again!

Stevens Rail Trail

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

October, 2023 by imaginetravelsgd

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Accordion

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

just walked the D & H trail from granville center to middle granville. really enjoyed the walk out toward middle granville but on the way back while walking through the farm (which was a delightful experience on the first trip through, seeing calves and cows) but then were charged by two pitties which attacked my dog and knocked me down. Luckily I had an umbrella and was able to get up and get away and down the trail. the dogs followed for a while but then returned to the farm. Too bad because was a very enjoyable walk until this. I just hope these two dogs dont really hurt someone....

Ammonoosuc Rail Trail

Poor condition

September, 2023 by joanhartzler

This trail is not suitable for biking at all. There are very large rocks and in places they dumped sand on the trail. Only rode from Littleton to Lisbon because the riding was so rough. We have hybrid bikes with suspension but we felt like it was way too rough! Never again! Get rid of the ATVs that tear up the trail or market this only to them! Âż

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.

I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.

Please put this one on your list to help!!!

Northern Rail Trail

Danbury Country Store to Tewksbury Pond, Grafton

September, 2023 by chriscarney

Parked across from the Danbury County Store. Headed west towards Grafton. Only saw a coupe peopling using the trail this late Friday afternoon. Trail was smooth and dry even with rain the prior day.

New Boston Rail Trail

perfect for walkers and bikers

September, 2023 by slasalle76

The trail guide book lists this as a 2-3 roughness, but I would keep it at 2. It's hard packed dirt or crushed gravel the whole length, and while I walked it due to the guide book description which said that half of it was really for walkers/hikers only, I competely disagree. If you want to ride, feel free to, as it's in great shape for all manner of bikes except a strictly road bike, as I assume road bikers want asphalt to ride on. I'll go back and do it again on my hybrid. I parked at Gregg Mills Rd, plenty of spaces, and there is parking for at least a few cars at all other intersections as well. Benches all along the way as well, so bring a picnic.

Monadnock Recreational Rail Trail

not great conditions

September, 2023 by emilyahagan

A mix of sand, packed gravel and flooded trail. Rather challenging terrain that required skilled navigating the trail . It was in horrible condition. The brewery in winchendon was wonderful, but you need to bushwhack through the trail and into an abandoned factory’s parking lot.

Monadnock Recreational Rail Trail

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer day

September, 2023 by bplatt1

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer day

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