Windsor, VT Bike Trails and Maps

445 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

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

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

57.8 mi
State: NH
Cinder, Crushed Stone

Old Railroad Trail

2.7 mi
State: NH
Dirt

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

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

Village Spur Rail Trail

2.1 mi
State: NH
Asphalt, Dirt, Grass
Accordion

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 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
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
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 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 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
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
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
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
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
Accordion
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

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.

Accordion

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

Delaware and Hudson Rail-Trail

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

June, 2024 by mdnkcn

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

Northern Rail Trail

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

June, 2024 by klracicot

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

Laverack Nature Trail at Hawkins Brook

An All Person Trail

June, 2024 by 7zvnmykbyx

This trail was designed with accessibility in mind. There is ample parking. Half the trail is in the sun and the rest is shaded. There is a combination of boardwalk and sustainable trail. People who use mobility devices - manual chairs, scooters, electric wheelchairs will find this a user friendly trail. It’s quiet, follows a brook, and is teeming with birds. There is also informational signs along the trail that describe the habitat. ,

WOW Trail

Ok Trail

May, 2024 by justin.c.perry84

This was an OK trail. We enjoyed that it was pretty well marked with the exception of one crossing near some train tracks. Too many road crossing points. Portions of the trail were rough because of roots growing under the pavement. We actually saw a runner take a pretty nasty spill because of the rough surface. It was nice to check it out, but we won’t go out of our way to come back.

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