Windsor, VT Bike Trails and Maps

476 Reviews

Looking for the best Bike trails around Windsor?

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

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Activities
Length
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Type
24 Results
Activities
Length
Surfaces
Type

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Lake Winnisquam Scenic Trail

1.58 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

Northern Rail Trail

59 mi
State: NH
Cinder, Crushed Stone

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

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

Fort Hill Recreational Rail Trail

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

Old Railroad Trail

2.7 mi
State: NH
Dirt

Stevens Rail Trail

1.65 mi
State: NH
Crushed Stone, Gravel

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

Concord-Lake Sunapee Rail Trail

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

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
Accordion

Village Spur Rail Trail

2.1 mi
State: NH
Asphalt, Dirt, Grass

Henniker & Hopkinton Rail Trails

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

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
Harrisville and Hancock Rail Trails run for 6 miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris Center...
NH 6.1 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
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
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 1.58 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
Spanning 59 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...
NH 59 mi Cinder, Crushed Stone
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 21.4 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 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
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 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 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
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
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 River Trail...
NH 4.94 mi Asphalt, Crushed Stone, Dirt, Gravel
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 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
Accordion
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 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 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

West River Trail (Windham County)

Lovely birthday ride

September, 2025 by diatom1

We rode to the end of the trail, then continued on Rice Farm Rd. to the dangerous intersection. we missed the entrance to the trail on the way back, so got a good workout on some hilly spots on the road.
On the packed sand patches, keep an eye out for roots that can be a bit dicey. In some spots along the gravel sections, the gravel can be a bit loose, so pay attention to the trail.

Northern Rail Trail

Beautiful Trail, hard pack for easy riding

September, 2025 by brenda.viglienzoni

Beautiful trail. Enjoyed the sites, sounds and smells. It runs along the river. I got on at the Depot Rd parking lot in Boscawen. Very easy access and plenty of parking. I Road 15 miles. The trail is fairly level with very little incline.

Ashuelot Recreational Rail Trail

Awesome Trail!

September, 2025 by mtheis.45

First time and loved it! I rode the entire route, starting at the south end parking lot. (42.758592, -72.471175) This trail has some unique features and the scenery is beautiful as you ride next to the river and through the woods. As a former rail, this trail has nice and gradual elevation changes and has fun bridges, which all seem to be maintained well.

At the time of my ride (end of Aug, '25) there were a couple of detours around mile 14 and 16 (heading north) but they have good (not great) detour signs listed to continue the route with a short road detour. As some folks mentioned, there are a few areas that look like they would be pretty wet during the wet season, but I had no issues with any area of the trail and never had to stop for downed trees in the way.

I rode my gravel setup (no suspension, 35mm tires) and had a blast! I'd highly recommend the trail and hope to be back for another spin soon.

Accordion

Fort Hill Recreational Rail Trail

We found this trail to be well maintained. Not as smooth as some rail trails, but smooth enough on our full suspension fat tire bikes. Hard tails may not enjoy as much. Nice scenery along the Connecticut river.

August, 2025 by jimthurber13

We found this trail to be well maintained. Not as smooth as some rail trails, but smooth enough on our full suspension fat tire bikes. Hard tails may not enjoy as much. Nice scenery along the Connecticut river.

Delaware and Hudson Rail-Trail

Southern Portion

August, 2025 by n22dknvqnt

We biked from Granville to Rupert, 11 miles one way. It was an excellent ride! The trail is in great shape and parking on Water St. by the Slate Valley Museum was very convenient. I believe the trail continues another 2 miles into West Rupert. If you like gravel rides, I highly recommend this one!

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Not what we expected

August, 2025 by rmitera36

We started at Walpole after searching for the trailhead parking lot finally parked our car thanks to the locals at the Irving station. We almost didn’t recognize the trail because it was grass. There were no markings and we found ourselves initially at the river at the boat launch because we didn’t realize that was the trail we were following. After backtracking, we followed the other grass trail toward Keene. Although there were portions that were dirt and gravel, the 9 mile ride that we managed to cover at 6 miles an hour with primarily grass. After an hour and a half, we realize we are only halfway to our destination of Keene and we turned back.. I recommendation would be not to start in Wall Paul, but to start and keen where the trail is paved

New Boston Rail Trail

wonderful ride

August, 2025 by trainman1957

We went there today! What a super fast fun trail! Lots to see and do ! Bring a picnic lunch and spend the day!!!

Warren to East Haverhill Railroad Grade Trail

ride the rocket from Warren to East Haverill

August, 2025 by pnelson4

Starting at the rocket site in Warren there was heavy ATV traffic kicking up enough dust to make the bike ride less enjoyable than it would be w/o them. The section from GlenCliff to E.Haverill where ATVs are not allowed is heavily overgrown and could really use a fully groomed makeover. We ride gravel bikes not mountain bikes and bailed out onto Rt 118 partway along due to poor trail conditions. Scenic corridor with untapped potential if given some tender love and care.

Mascoma River Greenway

Short but fun

August, 2025 by georgerisktaker

Paved. Runs through Lebanon. This trail is a must if you are going to do the Northern Rail Trail.

Northern Rail Trail

Long ride - sore bottom

August, 2025 by georgerisktaker

Longest trail in State and is deservedly well rated by most. It is a consistently groomed crushed stone trail with few roots and rocks. Not many places to stop and sit which on a long ride can be helpful. Make sure to ride to the statue at the southern trail head.

Winnipesaukee River Trail

Worthy trail

August, 2025 by georgerisktaker

Most of the trip is a rail trail of good quality. The ride through Tilton is on the road and can be tricky at one intersection. The "About this Route" provides a good description. The Tilton end of the trail by MacDonalds and Super 8 is not for trail parking. Use the address shown which is within 1 mile of the end of the trail. Franklin is a great town to visit.

Lake Winnisquam Scenic Trail

Fun but short

August, 2025 by georgerisktaker

Great views and we enjoyed the changes in grade and the turns, but a very short trail. Must be combined with Winni Trail, but that is also short.

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