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Windsor, Vermont Trails and Maps

Looking for the best trails around Windsor, Vermont? Find the top rated trails in Windsor, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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TRAIL LENGTH SURFACE TRAIL MAP

Ammonoosuc Rail Trail

19 miles
The Ammonoosuc Rail Trail is open to ATVs and snowmobiles. The trail is rough is many places, making for even difficult mountain biking in some segments. Trail users will find diversions in the charming town of Bath (particularly the covered ...
Ballast
Dirt
Gravel
Sand

Appel Way Trail

1.3 miles
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 Park on its east end. It also links to the ...
Asphalt

Ashuelot Rail-Trail

21.2 miles
Given its covered bridges, historical aura and abundant wildlife, the Ashuelot Rail-Trail (a.k.a. Ashuelot River Trail) has plenty to offer. The 21.2-mile route follows the corridor of the Ashuelot Railroad, which operated from 1851 to 1983, ...
Ballast
Cinder
Crushed Stone
Dirt

Blackmount Rail Trail

5 miles
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 gravel road. In some places the rails are ...
Cinder
Gravel
Woodchips

Bobby Woodman Rail Trail

1.7 miles
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, the rail-trail approaches Monadnock Park, a ...
Dirt
Gravel

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.8 miles
The Cheshire Rail Trail stretches for nearly 33 miles between Route 12 near Bookseller Road and the New Hampshire–Massachusetts state line at Route 12. In Keene, the trail includes a beautiful stone arch bridge over the Ashuelot River. There ...
Ballast
Cinder
Dirt
Gravel
Sand

Common Pathway

6.5 miles
Common Pathway runs for nearly 7 miles from the south end of Peterborough north to Hancock. The trail is a combination of asphalt and gravel and follows an old railroad right-of-way along the Contoocook River. Begin the trail just south of ...
Asphalt
Crushed Stone

Cross Vermont Trail

30 miles
The Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of spring 2012, 30 miles of trail are built and scattered across the state. Each of these trails are listed below and ...
Asphalt
Concrete
Crushed Stone
Dirt
Grass
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Delaware and Hudson Rail-Trail

23.5 miles
The Delaware & Hudson Rail-Trail quietly rambles over the rolling hills and farmland of western Vermont along the state’s border with New York, dipping into its western neighbor at the community of Granville. It traces an old Delaware & Hudson ...
Asphalt
Cinder
Dirt
Grass
Gravel

East Branch Trail (VT)

5.1 miles
The East Branch Trail is a 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 Searsburg Reservoir and Deerfield River in ...
Gravel

East Branch and Zealand Valley Railroad Hike

18 miles
Are you looking for a multi-day hike on beautiful rail-trails through pristine wilderness of the White Mountains? Look no further. At midpoint, the nearest road is 7 miles in either direction. Because of its isolation, this hike offers a quiet, ...
Ballast
Dirt
Grass
Gravel
Sand

Fort Hill Branch Rail-Trail

8.9 miles
At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail Trail that proceeds 21 miles north to Keene. ...
Ballast
Cinder
Dirt
Gravel
Sand

Heritage Trail (Manchester)

0.9 miles
The Heritage Trail is managed by the state of New Hampshire to provide access to recreational and historical attractions across the state. Eventually, the north-south route along the former Boston and Maine Railroad corridor will stretch more ...
Asphalt

Hillsborough Recreational Rail Trail

7.8 miles
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 and wooded landscapes for nearly 8 miles. ...
Crushed Stone
Dirt

Jonathan Daniels Trail

0.9 miles
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 for a Keene native who was killed during the ...
Crushed Stone

Keene Industrial Heritage Trail

1 miles
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 works.
Asphalt

Lake Winnisquam Scenic Trail

5.3 miles
The Town of Belmont has been notified that it will receive $282,720 in federal dollars for the construction of the first phase of the Lake Winnisquam Scenic Trail. The Lake Winnisquam Scenic Trail will be approximately five miles in length from ...

Lamoille Valley Rail Trail

19.9 miles
The Lamoille Valley Rail Trail is a growing trail network across northern Vermont that will one day stretch 93 miles between St. Johnsbury and Swanton. The trail is being built along the former route of the Lamoille Valley Railroad, which once ...
Crushed Stone
Gravel

Lye Brook Falls Trail

2.2 miles
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 former logging railroad up a gradual slope paralleling ...
Gravel

Millstone Hill West Bike Path

2.4 miles
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 connect Barre, East Barre, Westerville, Graniteville ...
Asphalt
Ballast

Monadnock Branch Rail-Trail

7.2 miles
The scenic Monadnock Branch Rail-Trail travels for just over 7 miles from Webster Street in Jaffrey near the ball field to the New Hampshire–Massachusetts border. From Jaffrey to Rindge the trail is packed gravel, except for a paved section ...
Asphalt
Gravel

Montpelier & Wells River Trail

21.8 miles
The Montpelier & Wells River Trail occupies the former right-of-way of the old Montpelier & Wells River Railroad, which originally ran for 45 miles across northeast Vermont. Called the "Granite Train" for the materials it often carried from ...
Ballast
Dirt
Gravel
Sand

Nanamocomuck Trail

12 miles
The Upper and Lower Nanamocomuck Trails in White Mountain National Forest are accessible from Kancamagus Highway (SR 112) west of Conway. The trails are open for hiking in summer and cross-country skiing (ungroomed) in winter. The lower trails ...
Ballast

New Boston Rail Trail

4.5 miles
The 4 ½ mile New Boston Rail Trail is an enticingly beautiful former Boston & Maine rail line running from approximately route 114 at the New Boston/Goffstown border to the center of New Boston. There it culminates at the Hillsborough County ...
Dirt

Northern Rail Trail

58 miles
At 58 miles, the Northern Rail Trail spans Grafton and Merrimack counties and is the longest rail-trail in New Hampshire. The surface is cinder ballast in Grafton and 3/8” stone dust in Merrimack; both easily bikeable on hybrids or mountain ...
Cinder
Crushed Stone

Pisgah State Park Reservoir Trail

5 miles
Pisgah State Park includes over 13,300 acres of rough forested terrain, encompassing a complete watershed north of the Ashuelot River. Within the Cheshire County towns of Winchester, Chesterfield and Hinsdale, the park protects seven ponds (popular ...
Dirt

Ramblin Vewe Farm Trails

5 miles
The Ramblin' Vewe Farm Trails are part of the Ramblin' Vewe Farm Trust property, a non-profit organization that protects and preserves the farm, while conserving the heritage of working farms and rural landscapes. Part of their mission is to ...
Dirt
Grass

South Barre Bike Path

1 miles
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 School, which is the location of the only ...
Asphalt

Stevens Rail Trail

1.3 miles
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 for just over a mile, unpaved and scenic, ...
Dirt
Gravel

Sugar River Trail

9.8 miles
Also known as the Sugar River Recreational Trail, this picturesque 9.8-mile path stretches from Newport to the southeastern edge of Claremont along the banks of the Sugar River. To reach Claremont proper, you can seamlessly connect to the Bobby ...
Ballast
Cinder
Sand

Toonerville Rail-Trail

3.1 miles
The Toonerville Rail-Trail (a.k.a. Springfield Greenway) spans 3 meticulously maintained miles from the downtown business district of Springfield southeast to the western bank of the Connecticut River at the Vermont–New Hampshire border. The ...
Asphalt

Valley Trail

0.8 miles
The scenic Valley Trail currently runs nearly a mile through West Dover in southern Vermont on the outskirts of the Green Mountain National Forest. Plans call for continuing the trail further north to the Mount Snow Ski Area and south to Wilmington, ...
Asphalt

WOW Trail

1.3 miles
The WOW Trail will one day stretch more than 9 miles in central New Hampshire along the Winnipesaukee Scenic Railroad. Its acronym comes from three regional lakes, which will be seen from the pathway: Winnisquam, Opechee, and Winnipesaukee. The ...
Asphalt

Warren to East Haverhill Railroad Grade Trail

10.7 miles
The Warren to East Haverhill Railroad Grade Trail starts from an interesting landmark: a Redstone missile brought to Warren by a resident who served in the Army in Alabama in 1970. He found some obsolete missiles in a field and arranged with ...
Dirt

West River Trail

16 miles
Following the floodplain of the West River Valley, the 16-mile West River Trail (a.k.a. Railroad Bed Trail) appeals to a wide range of trail users. The rail-trail has a nearly level surface, ideal for walkers, cyclists and equestrians, while ...
Gravel
Sand

Winnipesaukee River Trail

5.1 miles
The Winnipesaukee River Trail courses along its namesake river, connecting the towns of Franklin and Tilton-Northfield. The trail passes through an unusual upside-down covered bridge—believed to be the nation's only one—listed on the National ...
Crushed Stone
Dirt