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Winchendon Walking Trails and Maps

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Looking for the best Walking trails around Winchendon?

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

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Activities
Length
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69 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail
54.6 mi
State: CT
Ballast, Dirt, Gravel

Appel Way Trail
1.3 mi
State: NH
Asphalt

Ashburnham Rail Trail
1.3 mi
State: MA
Dirt

Ashuelot Recreational Rail Trail
21.5 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Assabet River Rail Trail
8.6 mi
State: MA
Asphalt

Barker Road Trail
0.9 mi
State: MA
Dirt, Grass

Bay Colony Rail Trail
1.7 mi
State: MA
Crushed Stone

Bobby Woodman Rail Trail
1.7 mi
State: NH
Dirt, Gravel

Bradford Rail Trail
1.3 mi
State: MA

Bridge of Flowers
0.1 mi
State: MA
Concrete

Bruce Freeman Rail Trail
11.7 mi
State: MA
Asphalt

Canalside Rail Trail
3.6 mi
State: MA
Asphalt

Center Trail
0.6 mi
State: MA
Crushed Stone

Charles River Bike Path
22.9 mi
State: MA
Asphalt

Cheshire Rail Trail (Cheshire Branch Rail Trail)
32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Chicopee River Canal Rail Trail
0.21 mi
State: MA
Asphalt

Cochituate Rail Trail
1.1 mi
State: MA
Asphalt, Concrete

Common Pathway
5.5 mi
State: NH
Asphalt, Crushed Stone

Concord River Greenway
2 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway
5.4 mi
State: MA
Asphalt
Accordion

Derry Rail Trail
3.6 mi
State: NH
Asphalt

East Branch Trail (VT)
0.5 mi
State: VT
Gravel

Fort Hill Recreational Rail Trail
7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Goffstown Rail Trail
5.5 mi
State: NH
Dirt, Grass, Gravel, Sand

Grand Trunk Trail
6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail
3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Haggetts Rail Trail
2 mi
State: MA
Crushed Stone

Harrisville Rail Trail
1.6 mi
State: NH
Dirt

Head’s Pond Trail
1.75 mi
State: NH
Gravel

Heritage Trail (Manchester)
0.9 mi
State: NH
Asphalt

Hillsborough Recreational Rail Trail
7.8 mi
State: NH
Crushed Stone, Dirt

Hoot, Toot and Whistle Trail
0.5 mi
State: VT
Dirt

Jonathan Daniels Trail
0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Londonderry Rail Trail
3.3 mi
State: NH
Asphalt

Lowell Canal System Trails
1.9 mi
State: MA
Asphalt, Concrete

Manhan Rail Trail
9.6 mi
State: MA
Asphalt

Mason Railroad Trail
6.7 mi
State: NH
Ballast, Gravel, Sand

Mass Central Rail Trail
38 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Methuen Rail Trail
2.4 mi
State: MA
Crushed Stone

Mine Falls Park
9.7 mi
State: NH
Asphalt, Crushed Stone, Dirt, Grass

Minuteman Commuter Bikeway
10.1 mi
State: MA
Asphalt

Monadnock Recreational Rail Trail
7.5 mi
State: NH
Asphalt, Gravel

Narrow-Gauge Rail-Trail
3 mi
State: MA
Asphalt, Crushed Stone, Dirt

Nashua Heritage Rail-Trail
1.3 mi
State: NH
Asphalt

Nashua River Rail Trail
12.3 mi
State: MA, NH
Asphalt

New Boston Rail Trail
3.9 mi
State: NH
Dirt

North Central Pathway
8.9 mi
State: MA
Asphalt

Northern Rail Trail
57.6 mi
State: NH
Cinder, Crushed Stone

Piscataquog Trail
2.1 mi
State: NH
Asphalt

Redstone Rail Trail
1.4 mi
State: MA
Asphalt

Reformatory Branch Trail
3.9 mi
State: MA
Dirt

Rockingham Recreational Rail Trail (Fremont Branch)
18.3 mi
State: NH
Dirt, Sand

Rockingham Recreational Rail Trail (Portsmouth Branch)
28.1 mi
State: NH
Crushed Stone, Dirt, Grass, Gravel, Sand

Salem Bike-Ped Corridor
1.15 mi
State: NH
Asphalt

South Manchester Rail Trail
0.89 mi
State: NH
Asphalt

South Spencer Rail Trail
1.62 mi
State: MA
Crushed Stone

Southern New England Trunkline Trail
22 mi
State: MA
Asphalt, Ballast, Crushed Stone

Spicket River Greenway
3.5 mi
State: MA
Asphalt

Stevens Rail Trail
1.3 mi
State: NH
Dirt, Gravel

Sugar River Trail
9.5 mi
State: NH
Ballast, Gravel, Sand

Toonerville Rail-Trail
3.2 mi
State: VT
Asphalt

Upper Charles Trail
13.2 mi
State: MA
Asphalt, Crushed Stone

Upper Falls Greenway
1 mi
State: MA
Crushed Stone

Valley Trail
9.1 mi
State: VT
Asphalt

Ware River Rail-Trail
12 mi
State: MA
Ballast, Dirt, Grass, Gravel

West River Trail

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

Westville Lake Community Trail
0.7 mi
State: MA
Crushed Stone

Windham Rail Trail
4.3 mi
State: NH
Asphalt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
 CT 54.6 mi Ballast, Dirt, Gravel
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
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
 MA 1.3 mi Dirt
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
 NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
The Assabet River Rail Trail connects five old mill towns that owe their revitalization to present-day high-tech industries. A midpoint gap splits the 8.6-mile paved trail, though long-range plans...
 MA 8.6 mi Asphalt
Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...
 MA 0.9 mi Dirt, Grass
The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...
 MA 1.7 mi Crushed Stone
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
The newly open Bradford Rail Trail occupies the former Pan Am rail lines, beautifying an area that once lay strewn with garbage and weeds. The city and numerous dedicated volunteers created the...
 MA 1.3 mi
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
 MA 0.1 mi Concrete
Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...
 MA 11.7 mi Asphalt
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
 MA 3.6 mi Asphalt
The Center Trail runs for less than a mile from Hopkinton's downtown to its high school and middle school, providing a safe route to school for thousands of students. The wooded trail, which once...
 MA 0.6 mi Crushed Stone
The Charles River Bike Path, also referred to as the Charles River Greenway, offers a paved, 22-mile route from Boston to its western suburbs. The trail is also part of a larger, developing network...
 MA 22.9 mi Asphalt
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
 MA 0.21 mi Asphalt
The Cochituate Rail Trail (CRT) is a developing, multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. Currently, its northernmost mile in...
 MA 1.1 mi Asphalt, Concrete
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
The health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
 MA 2 mi Asphalt
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
 MA 5.4 mi Asphalt
Accordion
This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
 NH 3.6 mi Asphalt
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
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 year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
 NH 5.5 mi Dirt, Grass, Gravel, Sand
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
 MA 6.2 mi Crushed Stone, Dirt, Gravel
Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
 NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...
 MA 2 mi Crushed Stone
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
The Head’s Pond Trail (formerly known as Hooksett Rail Trail) is a 1.9-mile rail-trail that visits two scenic ponds, including the eponymous Head’s Pond, in a woodsy area of Hooksett. The trail’s...
 NH 1.75 mi Gravel
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...
 NH 0.9 mi Asphalt
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 0.5 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
The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 3.3-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
 NH 3.3 mi Asphalt
Lowell's Canal System Trails are part of Lowell National Historical Park in Lowell, Massachusetts. The park preserves some of America's industrial past: its 19th-century textile mills formed the first...
 MA 1.9 mi Asphalt, Concrete
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
 MA 9.6 mi Asphalt
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
 NH 6.7 mi Ballast, Gravel, Sand
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
 MA 38 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Methuen Rail Trail connects three communities in northeastern Massachusetts as it follows the route of the former Manchester and Lawrence Branch of the Boston and Maine Railroad. The rail-trail's...
 MA 2.4 mi Crushed Stone
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
 NH 9.7 mi Asphalt, Crushed Stone, Dirt, Grass
Many commuters choose the Minuteman Commuter Bikeway for freedom from congested traffic in the northwest Boston suburbs. For others, the 10.1-mile paved trail between Cambridge and Bedford serves as a...
 MA 10.1 mi Asphalt
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
Even though the Narrow-Gauge Rail-Trail traces the nation’s first narrow-gauge railroad for 3 miles from Bedford toward Billerica, the mostly crushed-stone path is plenty wide enough now to...
 MA 3 mi Asphalt, Crushed Stone, Dirt
The Nashua Heritage Rail Trail begins adjacent to City Hall on Main Street in downtown Nashua. It is a short trail that takes you through one of the first neighborhoods that was planned and built in...
 NH 1.3 mi Asphalt
The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...
 MA, NH 12.3 mi Asphalt
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 North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
 MA 8.9 mi Asphalt
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
 NH 57.6 mi Cinder, Crushed Stone
The Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...
 NH 2.1 mi Asphalt
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
 MA 1.4 mi Asphalt
The Reformatory Branch Trail connects the historical towns of Bedford and Concord along a nearly 4-mile dirt path through wildlife refuges that ends where soldiers witnessed “the shot heard round the...
 MA 3.9 mi Dirt
Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
 NH 18.3 mi Dirt, Sand
The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...
 NH 28.1 mi Crushed Stone, Dirt, Grass, Gravel, Sand
When complete, the Salem Bike-Ped Corridor will run for more than 5 miles on a former Boston and Maine Railroad corridor from connections with the Windham Rail Trail (north) and Methuen Rail Trail...
 NH 1.15 mi Asphalt
The South Manchester Rail Trail is a proposed bike/pedestrian path that would connect the downtown Millyard area of Manchester to the Town on Londonderry. The South Manchester Rail Trail will utilize...
 NH 0.89 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
 MA 1.62 mi Crushed Stone
The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
 MA 22 mi Asphalt, Ballast, Crushed Stone
The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...
 MA 3.5 mi Asphalt
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...
 NH 1.3 mi Dirt, 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 developing Upper Charles Trail will one day total 24 miles, linking the communities of Milford, Ashland, Sherborn, Holliston, Framingham, and Hopkinton along a former railroad bed. As of 2018,...
 MA 13.2 mi Asphalt, Crushed Stone
The Upper Falls Greenway is a short rail-trail that cuts through the charming village of Newton Upper Falls in Newton, Massachusetts. The trail occupies the same former rail corridor as the developing...
 MA 1 mi Crushed Stone
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 Route 100....
 VT 9.1 mi Asphalt
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
 MA 12 mi Ballast, Dirt, Grass, Gravel
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
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
 MA 0.7 mi Crushed Stone
The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
 NH 4.3 mi Asphalt

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Trails by activity

Concord River Greenway

MA - 2 miles

The health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...

Bay Colony Rail Trail

MA - 1.7 miles

The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...

Spicket River Greenway

MA - 3.5 miles

The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...

Methuen Rail Trail

MA - 2.4 miles

Methuen Rail Trail connects three communities in northeastern Massachusetts as it follows the route of the former Manchester and Lawrence Branch of the Boston and Maine Railroad. The rail-trail's...

Accordion

Center Trail

MA - 0.6 miles

The Center Trail runs for less than a mile from Hopkinton's downtown to its high school and middle school, providing a safe route to school for thousands of students. The wooded trail, which once...

Piscataquog Trail

NH - 2.1 miles

The Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...

Canalside Rail Trail

MA - 3.6 miles

The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...

Granite Town Rail-Trail

NH - 3 miles

Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...

Bruce Freeman Rail Trail

MA - 11.7 miles

Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...

Upper Falls Greenway

MA - 1 miles

The Upper Falls Greenway is a short rail-trail that cuts through the charming village of Newton Upper Falls in Newton, Massachusetts. The trail occupies the same former rail corridor as the developing...

North Central Pathway

MA - 8.9 miles

The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...

Londonderry Rail Trail

NH - 3.3 miles

The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 3.3-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...

Mass Central Rail Trail

MA - 38 miles

The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...

Connecticut Riverwalk and Bikeway

MA - 5.4 miles

The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Valley Trail

VT - 9.1 miles

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 Route 100....

Stevens Rail Trail

NH - 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...

Lowell Canal System Trails

MA - 1.9 miles

Lowell's Canal System Trails are part of Lowell National Historical Park in Lowell, Massachusetts. The park preserves some of America's industrial past: its 19th-century textile mills formed the first...

Jonathan Daniels Trail

NH - 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...

More Winchendon bike trailsView Fewer Winchendon bike trails

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...

Canalside Rail Trail

MA - 3.6 miles

The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...

Mason Railroad Trail

NH - 6.7 miles

The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...

East Branch Trail (VT)

VT - 0.5 miles

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...

Accordion

Cochituate Rail Trail

MA - 1.1 miles

The Cochituate Rail Trail (CRT) is a developing, multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. Currently, its northernmost mile in...

Piscataquog Trail

NH - 2.1 miles

The Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...

Mass Central Rail Trail

MA - 38 miles

The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...

Methuen Rail Trail

MA - 2.4 miles

Methuen Rail Trail connects three communities in northeastern Massachusetts as it follows the route of the former Manchester and Lawrence Branch of the Boston and Maine Railroad. The rail-trail's...

Mine Falls Park

NH - 9.7 miles

Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...

Toonerville Rail-Trail

VT - 3.2 miles

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...

Bruce Freeman Rail Trail

MA - 11.7 miles

Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...

Minuteman Commuter Bikeway

MA - 10.1 miles

Many commuters choose the Minuteman Commuter Bikeway for freedom from congested traffic in the northwest Boston suburbs. For others, the 10.1-mile paved trail between Cambridge and Bedford serves as a...

Spicket River Greenway

MA - 3.5 miles

The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Northern Rail Trail

NH - 57.6 miles

Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...

Redstone Rail Trail

MA - 1.4 miles

The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Bridge of Flowers

MA - 0.1 miles

The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...

Stevens Rail Trail

NH - 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...

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Common Pathway

NH - 5.5 miles

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...

Monadnock Recreational Rail Trail

NH - 7.5 miles

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...

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Stevens Rail Trail

NH - 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...

Accordion

Cochituate Rail Trail

MA - 1.1 miles

The Cochituate Rail Trail (CRT) is a developing, multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. Currently, its northernmost mile in...

Mason Railroad Trail

NH - 6.7 miles

The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...

Cheshire Rail Trail (Cheshire Branch Rail Trail)

NH - 32.9 miles

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...

Ashuelot Recreational Rail Trail

NH - 21.5 miles

The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...

Harrisville Rail Trail

NH - 1.6 miles

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...

Bruce Freeman Rail Trail

MA - 11.7 miles

Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...

Bobby Woodman Rail Trail

NH - 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,...

Keene Industrial Heritage Trail

NH - 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...

Salem Bike-Ped Corridor

NH - 1.15 miles

When complete, the Salem Bike-Ped Corridor will run for more than 5 miles on a former Boston and Maine Railroad corridor from connections with the Windham Rail Trail (north) and Methuen Rail Trail...

Methuen Rail Trail

MA - 2.4 miles

Methuen Rail Trail connects three communities in northeastern Massachusetts as it follows the route of the former Manchester and Lawrence Branch of the Boston and Maine Railroad. The rail-trail's...

Bridge of Flowers

MA - 0.1 miles

The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Fort Hill Recreational Rail Trail

NH - 7 miles

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...

Appel Way Trail

NH - 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...

Hoot, Toot and Whistle Trail

VT - 0.5 miles

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...

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

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Recent Trail Reviews

Charles River Bike Path

Best Bike ride - a must do

September, 2018 by jnich8888

We parked in Newton and rode out bikes all the way to the Cambridge Galleria and had lunch. Then we rode back to Newton, was just over 27 miles round trip. Mostly along the river. The trail is broken up and we crossed the river about 3 times in Watertown to Waltham, but what an amazing ride. Some dirt sections, but our Trek hybrids did not have trouble. Be careful crossing streets, espcially in the city. Also, don't go full speed as there are a lot of people walking and enjoying the trail, so take your time and enjoy!

read more …

Bruce Freeman Rail Trail

Lovely surprise trail

September, 2018 by lisa.berelson

A brand new bridge has been constructed which crosses 2A seamlessly connecting this (at present) Chelmsford to Acton path. A fully paved, and at times exceptionally wide, path passes through marshland and lovely new wood feel ferns, lovely ponds/small beaches. It was a pleasure taking this 12.5 mile ride which had plenty of canopy covering on a sunny day. The description may be a little outdated b/c we saw newer looking parking on various parts of the trail and actually started in Acton. As always a bunch of street crossings to be cautious about with older style raised brick stanchions at these intersections to encourage reduced speed.

read more …

Air Line State Park Trail

Response to Construction News

September, 2018 by blueskye

In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.

read more …
Accordion

Methuen Rail Trail

Newly Paved

September, 2018 by minion450

Project is just about done. parking lot at the depot still being worked on but from Lawrence to Salem NH all paved. southern portion of the trail still a little trashy off the trail but major improvement to say the least.

read more …

Air Line State Park Trail

Construction News

September, 2018 by CW4

I just road the Airline Trail across the Willimantic River and then toward the newer ending at Mackie's Ag. Store near the Columbia town line. It was in fine shape. However, what I was looking for is evidence that the work on the Willimantic River bridge was started. I found nothing underway. I road to the easterly end of the Hop River Trail hoping that it was starting at that end. No such luck. Does anyone out there have any information on when this section will be started?

read more …

Upper Charles Trail

Nice easy ride

September, 2018 by sboulet

Nice easy ride. After Washington Secondary and East Bay, this is a nice relaxing ride.

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Rockingham Recreational Rail Trail (Portsmouth Branch)

A difficult start, a great finish

September, 2018 by robert.richter89

I started at the Massabesic Lake trailhead which offered plenty of parking as well as a beautiful start to my ride. There were no mile markers or any history signs on the trail so mileage is difficult to track. The first four to five miles of my ride were very rough with large rocks strewn all over the trail and three tunnels underneath roadways. The rocks in this section are all very well marked by orange spray paint, I just had to take my time on my hybrid bike. A hybrid bike will do just fine on the trail but a mountain bike would offer more confidence in this section.

After this first section of trail I found the rest of the trail to offer beautiful scenery as well as a much smoother ride. There are a fair share of road crossings but all but two are very quiet roads that had very little traffic. Raymond offers the perfect mid-trail stop to take pictures as well as a place to get food. Epping also offers more places to get refreshments. The last stretch of the trail from Epping to Newfields was my favorite part of the trail and offered an easy finish to my ride.

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Bruce Freeman Rail Trail

Excellent trail

September, 2018 by gmc22

Though I only went about 6 or 7 miles into this trail, I found it to be scenic, safe, and flat. Some segments of the trail are wider than usual. There are a couple of swim-able ponds along it if you want to stop for a dip. Overall, an excellent trail and I look forward to doing it in its entirety, next time.

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Hoot, Toot and Whistle Trail

Rock, Root, and Tree

September, 2018 by jennifer81

This trail is not at all as described. It started off on crushed gravel for a few hundred yards. As soon as it entered the woods it became a foot path of a nearly contiguous stretch of single-track biking with (occasionally without) large roots and rocks to navigate. We walked our bikes more than we rode them and went a half mile without getting to the reservoir before finally turning around.

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Ashuelot Recreational Rail Trail

Difficult Trail through somewhat scenic country

August, 2018 by natwelch

I started the trail in Hinsdale, and found it reasonably rideable (I use a Specialized hybrid) through Winchester and a few miles beyond. However, the trail started to get rougher including some wet areas. I came to a spot where it followed high tension lines and by the time I got to the monadnock speedway, I was done. I went back to Winchester via Rt 10 and then caught the trail back to my car. Not my favorite trail, but if you have the bike and the inclination, it could be fun for you

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Ashuelot Recreational Rail Trail

August 2018

August, 2018 by bdrzyzga

We started the trail in Keene. The first 5 miles were nice, but we had to dodge pretty deep chipmunk holes. The trail is very poorly marked and we missed seeing the Sawyer Crossing Covered bridge which could not be seen by the trail. After 7.5 miles we got turned around by heavy mud, water and a downed tree. I would say this trail might be perfect for equestrians and aggressive mountain bikers.

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Fort Hill Recreational Rail Trail

Needs maintenance

August, 2018 by lrhecker47_tl

I tried to access this trail from the northern end which proved impossible. There is no road access until you get to parking areas on either end of the causeway. The trail is not marked with any signage at those places, either, but the track is evident when you cross into the fishing access parking areas off Rt 119. As mentioned, the trail is muddy and filled with puddles during this rainy August, and several trees across the trail. I was not able to reach the northern end because of a very large, multi-branched tree across the trail about a mile south of there. But it was pleasant riding close to the Connecticut River and there were almost no other people on the trail on a weekday.

read more …
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