Windsor, VT Running Trails and Maps

449 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
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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

1.58 mi
State: NH
Asphalt

Laverack Nature Trail at Hawkins Brook

0.6 mi
State: NH
Boardwalk, Crushed Stone

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

West River Trail (Windham County)

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

Ashuelot Recreational Rail Trail

21.4 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)

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

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

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

Old Railroad Trail

2.7 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

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

Ammonoosuc Rail Trail

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

Concord-Lake Sunapee Rail Trail

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

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

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
Overview 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...
NH 1.58 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 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 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...
NH 21.4 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
Overview The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of...
NH 42.4 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
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
Overview The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where there is a 4-mile gap. This border area is...
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
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
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
Overview  The Sugar River Trail runs for 9.5 miles between Claremont and Newport along the old Sugar River Railroad corridor. The 9.5-mile trail crosses its namesake river seven times—twice on...
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
Overview 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...
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
Overview The Winnipesaukee River Trail runs for nearly 5 miles between the towns of Franklin and Tilton, nestled in the White Mountains of New Hampshire. About the Route The Winnipesaukee...
NH 4.94 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
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
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 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

Common Pathway

Nice trail ride with a great finishing destination

November, 2024 by georgerisktaker

The Common Pathway is also called the Peterborough RT. This RT adjoins the Old Railroad Trail and is about 5 miles north of Monadnock RT (we did all 3 trails the same day). The trail is mostly crushed stone but some asphalt as well as road ride. Some rough spots but no issue. Started at Trailhead for Old Railroad Trail and headed toward Peterborough. It is a nice town with several good eating and drinking places. Good trail and the Contoocook River runs along most of the trail. We did not do the trail south of Peterborough as it went from town, along 202 (traffic at 50+ mph) and was not reviewed as being an interesting ride.

Old Railroad Trail

Rustic and bumpy deep woods ride (good feel)

November, 2024 by georgerisktaker

e-Bike with 2" tires. The trail adjoins Peterborough (Common Path) RT. Rough trail with roots and rocks, so speeds above 10 are impossible to maintain. On a positive note, you really feel like you are in the woods. We were able to go slightly longer than the miles posted. A tiring short ride, but doable. Wife hated it, as too bumpy. Recommendation: ride Peterborough (Common Path) first as it is much easier.

Monadnock Recreational Rail Trail

Monadnock Recreational Rail Trail

November, 2024 by georgerisktaker

Biked with e-bikes 2" tires. From the north going south (American Legion Baseball Field). Mostly crushed stone trail. Feels like a rail trail - level and wide. Only one rough area (RR ties and rocks for about 10 yds). The water on the left of the trail looked like it was drying up (no smell) and there was at least one nice lake (average views). Part of the trail runs along the highway. Only rode 5 miles as we didn't go much south of 202 (exceedingly difficult crossing at rush hour - be careful). Some of the reviews of the area south of where we rode indicate more difficult terain.

Accordion

Cheshire Rail Trail (Cheshire Branch Rail Trail)

hazardous obstacle course

October, 2024 by bikerdoc

My wife and I are both injured(fortunately not serious) after both of us thrown off our bikes simultaneously on a small poorly surfaced wooden bridge just north of Keene NH. The wooden boards were uneven and some rotted causing our bikes to wedge in a step-off causing us both to fall off our bikes. The trail had several road crossings just outside of the town of Keene which are very dangerous. There are tiny stop sign markings on the trail and no large or blinking light warnings on the crossing roads which have poor visibility in both directions due to curving of the road. I would not recommend this trail for transient travelers trying a new RT on vacation. This is for locals only who know the trail well in my opinion.

Sugar River Trail

Not for bicycles!

October, 2024 by jimblackjim7

The scenery is very nice which is why I gave it more than one star. The surface is sand. Sometimes pretty well packed. Other times quite loose. It was doable with our hybrid bikes, but a lot of work and not much fun. Add to this a steady stream of dirt bikes and 4x4s kicking up dust and spewing fumes! Just not our kind of cycling.

Ammonoosuc Rail Trail

No Longer a trail for bicycles

October, 2024 by gjerstak

We road 5 miles of the trail starting in Littleton.
But after 5 miles we turned back because ATV's have torn-up the trail.
This trail is OK for walking, but no longer OK for bicycles.
It is sad. It would be a nice trail if the ATV's had not destroyed it.

WOW Trail

wow trail

September, 2024 by r1paull

Sept 30th not a good trail ! We ran into several meth heads and police taking them into custody, Scarey stuff to say the least. We will not be back.

Fort Hill Recreational Rail Trail

great trail

September, 2024 by leslie.sherman316

We did this trail today. It is quite bumpy but the scenery more than makes up for that. It goes through beautiful forests with frequent views of the Connecticut River. Don’t pass it up if you are in the area.

Ammonoosuc Rail Trail

Trail is outstanding!

September, 2024 by ponttichuck

Whatever the previous people experienced has been taken care of … the only obstacles are the barriers you go around preventing atvs from using the trail … it’s not a paved trail but it is very smooth for a natural trail… its absolutely gorgeous from Littleton to the nh border… today I am biking with my sister and brother in law and look forward to exploring the wonders of nature and enjoying every minute of it!

Winnipesaukee River Trail

well maintained with beautiful views of the river

August, 2024 by brenda.viglienzoni

This trail was lovely. I did the entire trail both ways in a couple of hours. Mostly flat and well maintained. Began in Tilton on Rt 140 and road to the end in Franklin. Many nice places to stop along the way. Took some great pictures. It was a bit confusing when the trail ends and you are routed down Main Street in Tilton. I almost turned around at this point. Honestly It’s really not that far through town. Just be careful of cars backing out of parking spots. The vistas are worth it, keep going. Looking forward to checking out another trail.

Northern Rail Trail

great trail

August, 2024 by mflayhan

One of the best biking trails smooth great steady cruiser trail loved it

Concord-Lake Sunapee Rail Trail

so much to do

June, 2024 by carmen347

I have been waiting to try this route for several years. Always hearing that it wasn’t close to being finished. I was very disappointed to see firsthand that virtually nothing has been done for those years. The first mile from Concord is covered with packed cinder, but beyond that the trail is still raw and rough with exposed rocks and roots. Not sure why this project has stalled but I will not be riding it or supporting it until domething more is done to show progress. tiding it ir supporting it until I see something

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