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Winchester, MA Trails and Maps

1322 Reviews

Looking for the best trails around Winchester?

Explore the best rated trails in Winchester, MA. Whether you're looking for an easy walking trail or a bike trail like the Spicket River Greenway and Bridge Street Bike Trail. With more than 89 trails covering 533 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
90 Results
Activities
Length
Surfaces
Type

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

Amesbury Riverwalk
1.3 mi
State: MA
Asphalt

Ashburnham Rail Trail
1.3 mi
State: MA
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

Blackstone River Greenway
26.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Border to Boston Trail
10.7 mi
State: MA
Crushed Stone, Dirt

Boxford Rail Trail
2.1 mi
State: MA
Dirt, Grass

Bradford Rail Trail
1.3 mi
State: MA
Asphalt

Bridge Street Bike Trail
1 mi
State: MA
Asphalt

Bridle Trail

3 mi
State: MA
Dirt, Sand

Bruce Freeman Rail Trail
11.7 mi
State: MA
Asphalt

Burrillville Bike Path
1.2 mi
State: RI
Asphalt

Center Trail
0.6 mi
State: MA
Crushed Stone

Charles River Bike Path
22.9 mi
State: MA
Asphalt

Clipper City Rail Trail & Harborwalk
3.9 mi
State: MA
Asphalt, Boardwalk

Cochituate Rail Trail
1.1 mi
State: MA
Asphalt, Concrete

Concord River Greenway
2 mi
State: MA
Asphalt

Derry Rail Trail
3.6 mi
State: NH
Asphalt
Accordion

East Bay Bike Path
14.3 mi
State: RI
Asphalt

East Boston Greenway
2.8 mi
State: MA
Asphalt

Fred Lippitt Woonasquatucket River Greenway
6.8 mi
State: RI
Asphalt

Fresh Pond Bikeway

0.7 mi
State: MA
Asphalt

Gloria Braunhardt Bike Path
1.2 mi
State: MA
Asphalt, Dirt, Grass

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

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

Haggetts Rail Trail
2 mi
State: MA
Crushed Stone

Hanover Branch Rail Trail
2.6 mi
State: MA
Asphalt, Crushed Stone

Head's Pond Trail
1.75 mi
State: NH
Gravel

Heritage Trail (Manchester)
0.9 mi
State: NH
Asphalt

Independence Greenway
5.3 mi
State: MA
Asphalt

Jay McLaren Memorial Trail
2 mi
State: MA
Dirt, Grass, Gravel

Londonderry Rail Trail
4.5 mi
State: NH
Asphalt

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

Malden River Greenway
2.5 mi
State: MA
Asphalt, Crushed Stone

Marblehead Rail-Trail
4 mi
State: MA
Asphalt, Dirt, Gravel, Sand

Martin H. Burns Wildlife Management Area Trail
3.4 mi
State: MA
Dirt, Gravel, Sand

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
Asphalt, 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

Mystic River Greenway
4 mi
State: MA
Asphalt, Boardwalk

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

Neponset River Greenway
8.2 mi
State: MA
Asphalt

New Boston Rail Trail
3.9 mi
State: NH
Dirt

North Bank Bridge
0.5 mi
State: MA
Concrete

North Central Pathway
8.9 mi
State: MA
Asphalt

Northern Strand Community Trail
8 mi
State: MA
Asphalt, Crushed Stone

Norwell Pathway
2 mi
State: MA
Asphalt, Boardwalk

Old Eastern Marsh Trail
1.4 mi
State: MA
Asphalt

Old Railroad Trail
2.7 mi
State: NH
Dirt

Peanut Trail
1.5 mi
State: NH
Cinder

Pine Tree Brook / Popes Pond Path
2 mi
State: MA
Asphalt, Dirt, Woodchips

Piscataquog Trail
2.1 mi
State: NH
Asphalt

Quarries Foot Path
1 mi
State: MA
Dirt

Quinebaug Valley Rail Trail
5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

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

Roland Bergeron Bike Path
6 mi
State: NH
Asphalt

Rose Fitzgerald Kennedy Greenway
1.9 mi
State: MA
Asphalt, Concrete

Salem Bike-Ped Corridor
1.15 mi
State: NH
Asphalt

Salem-Beverly Canal Path (Grand Wenham Canal Path)
2 mi
State: MA
Dirt, Grass

Salisbury Beach State Reservation Trail
0.6 mi
State: MA
Crushed Stone, Grass

Salisbury Point Ghost Trail
1.8 mi
State: MA
Crushed Stone

Salisbury Rail Trail Connector
0.3 mi
State: MA
Asphalt

South Bay Harbor Trail
3.8 mi
State: MA
Asphalt, Boardwalk, Brick, Concrete

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

Southwest Corridor Park (Pierre Lallement Bike Path)
4.1 mi
State: MA
Asphalt

Spicket River Greenway
3.5 mi
State: MA
Asphalt

Stillwater Scenic Walkway
1 mi
State: RI
Crushed Stone, Dirt

Ten Mile River Greenway
3 mi
State: RI
Asphalt

Tri-Community Greenway
6.6 mi
State: MA
Asphalt

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

Upper Falls Greenway
1 mi
State: MA
Crushed Stone

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

Washington Secondary Bike Path
19.2 mi
State: RI
Asphalt

Watertown-Cambridge Greenway
0.7 mi
State: MA
Asphalt

Wellington Greenway
2.5 mi
State: MA
Asphalt

West Foss Farm Trail
1.6 mi
State: NH
Dirt

Whitney Spur Rail Trail
1.6 mi
State: MA
Asphalt, Crushed Stone

Windham Rail Trail
4.3 mi
State: NH
Asphalt

World War II Veterans Memorial Trail
1.5 mi
State: MA
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
The Amesbury Riverwalk (also known as the Powwow Riverwalk) carries visitors between a resurgent waterfront district on the Powwow River to a modern shopping center on the outskirts of this historical...
 MA 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 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
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
 MA, RI 26.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...
 MA 10.7 mi Crushed Stone, Dirt
The Boxford Rail Trail is a short, rustic pathway open on a former rail corridor in rural Essex County. Now home to overhead electric wires owned by National Grid, the trail is open via a license...
 MA 2.1 mi Dirt, Grass
The Bradford Rail Trail occupies a former Pan Am rail corridor, beautifying an area that once lay strewn with garbage and weeds. The city and numerous dedicated volunteers created the mile-long path...
 MA 1.3 mi Asphalt
The Bridge Street Bike Trail begins near Curtis Park and travels south through downtown Salem, closely following the Bridge Street Bypass. The short trail runs through residential, retail and...
 MA 1 mi Asphalt
Marshfield's Bridle Trail follows a former railroad bed through a tree-lined corridor. It begins at the town's Dandelion Park and heads north. Its compacted dirt surface is best suited for walking,...
 MA 3 mi Dirt, Sand
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
Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once...
 RI 1.2 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
The Clipper City Rail Trail is part of the Coastal Trails Coalition, which is developing in the four towns of Amesbury, Newbury, Newburyport, and Salisbury along the Merrimack River and will...
 MA 3.9 mi Asphalt, Boardwalk
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 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
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
Accordion
With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...
 RI 14.3 mi Asphalt
More and more, airport lands near previously under-used rail corridors are being transformed from largely neglected vacant lands into urban greenways. These new vibrant spaces are used not only by...
 MA 2.8 mi Asphalt
The Fred Lippitt Woonasquatucket River Greenway provides a valuable crosstown connector of nearly 7 miles from downtown Providence to the city’s western neighborhoods and the nearby town of Johnston....
 RI 6.8 mi Asphalt
The Fresh Pond Bikeway runs through Fresh Pond Reservation, a park in Cambridge, Massachusetts. The bikeway winds around the east edge of the Fresh Pond Reservoir. Part of the trail is on a road...
 MA 0.7 mi Asphalt
Although short, the scenic Gloria Braunhardt Bike Path travels through forests and pastures full of birds and wildlife. The asphalt pathway parallels the eastern side of the present-day Interstate 95...
 MA 1.2 mi Asphalt, Dirt, Grass
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
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
In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...
 MA 2.6 mi Asphalt, Crushed Stone
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
The 5.3-mile Independence Greenway makes for a pleasant ride, providing access to lakes, parks, and nature preserves. The paved pathway is located in the town of Peabody (pronounced by locals as...
 MA 5.3 mi Asphalt
Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...
 MA 2 mi Dirt, Grass, Gravel
The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 4.5-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
 NH 4.5 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 Malden River Greenway is part of the Mystic Greenways trail system, which also includes the Wellington Greenway and the Mystic River Greenway. When completed, it will run along the Malden River...
 MA 2.5 mi Asphalt, Crushed Stone
The Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 4-mile trail knits together a...
 MA 4 mi Asphalt, Dirt, Gravel, Sand
The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...
 MA 3.4 mi Dirt, Gravel, Sand
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 Asphalt, 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
The Mystic River Greenway is part of the Mystic Greenways trail system, which also includes the Wellington Greenway and the Malden River Greenway. When completed, the trail will connect the...
 MA 4 mi Asphalt, Boardwalk
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 Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...
 MA 8.2 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 Bank Bridge, which opened in 2012, provides a safe and convenient pedestrian and bicycle connection between Cambridge's North Point Park and Paul Revere Park in Charlestown. Spanning 690...
 MA 0.5 mi Concrete
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
The Northern Strand Community Trail is part of the visionary and almost-complete Bike to the Sea plan to link Boston and the Mystic River to the seashore in Lynn, north of Boston. It currently runs...
 MA 8 mi Asphalt, Crushed Stone
Norwell is a suburb about 30 minutes' drive south of Boston, Massachusetts. It is home to the Norwell Pathway, a 2-mile non-motorized trail that was constructed to give residents an alternative way to...
 MA 2 mi Asphalt, Boardwalk
The Old Eastern Marsh Trail (a.k.a the Salisbury Rail Trail) runs for 1.4 miles between the north bank of the Merrimack River and Mudnock Road in Salisbury. The beautifully landscaped trail was built...
 MA 1.4 mi Asphalt
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 Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...
 NH 1.5 mi Cinder
The Pine Tree Brook Trail travels alongside the brook in Milton, Massachusetts. The path travels through woods and residential neighborhoods for a distance of about 1.8 miles, and it connects to the...
 MA 2 mi Asphalt, Dirt, Woodchips
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 Quarries Foot Path offers a wooded 1-mile hiking route in western Quincy, about 10 miles south of Boston. Begin your adventure on the south side of Ricciuti Drive, which borders Quincy Quarries...
 MA 1 mi Dirt
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
 MA 5.7 mi Ballast, Cinder, Dirt, Grass
The Reformatory Branch Trail connects the historical towns of Bedford and Concord along a nearly 4-mile dirt path through wildlife refuges that ends a short distance from the North Bridge, 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
The Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...
 NH 6 mi Asphalt
Boston's Rose Kennedy Greenway may not be very long, but it's jam-packed with attractions. Along the paved pathway, you can access five parks, be wowed by public art, stop to smell the flowers in...
 MA 1.9 mi Asphalt, Concrete
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
Although only a grassy, hard-packed dirt pathway, the route along the Salem-Beverly Canal (also known as the Grand Wenham Canal), is scenic and peaceful. The old canal, built in 1917, lies between two...
 MA 2 mi Dirt, Grass
Although less than a mile, the trail running through Salisbury Beach State Reservation offers lovely views of the beaches off the northeastern coast of Massachusetts, just a few miles south of the New...
 MA 0.6 mi Crushed Stone, Grass
Currently 1.8 miles, the Salisbury Point Ghost Trail provides a peaceful walk or bike ride through the woods on a well-maintained stone-dust trail. The route is one part of the larger Coastal Trails...
 MA 1.8 mi Crushed Stone
The Salisbury Rail Trail Connector, also known as the Gillis Rail Trail Connector, is a 0.3-mile link between two rail-trails: Salisbury's Old Eastern Marsh Trail and Newburyport's Clipper City Rail...
 MA 0.3 mi Asphalt
The South Bay Harbor Trail connects several Boston neighborhoods—Lower Roxbury, the South End, Chinatown, and Fort Point Channel—to the Boston Harbor. The trail spans nearly 4 miles from Ruggles...
 MA 3.8 mi Asphalt, Boardwalk, Brick, Concrete
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 Southwest Corridor Park (Pierre Lallement Bike Path) knits together neighborhoods in southern Boston from the Back Bay to Jamaica Plain. Popular as a route for commuters as well as casual walkers,...
 MA 4.1 mi Asphalt
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
The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...
 RI 1 mi Crushed Stone, Dirt
Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...
 RI 3 mi Asphalt
The Tri-Community Greenway follows the route of the Boston and Lowell Railroad and its Stoneham Branch, originally built to serve Stoneham’s shoe factories and provide passenger service. The trail...
 MA 6.6 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
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 Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
 RI 19.2 mi Asphalt
The Watertown-Cambridge Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The trail begins in a busy shopping area on the site of a former U.S. Army arsenal. Trees...
 MA 0.7 mi Asphalt
The Wellington Greenway is a section of the Malden River Greenway in Medford, Massachusetts. Eventually, the Wellington Greenway will be connected to the other sections of the Malden River Greenway in...
 MA 2.5 mi Asphalt
The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...
 NH 1.6 mi Dirt
The Whitney Spur Rail Trail runs from just north of the MBTA’s Cohasset Station through dense woodlands to the edge of Wompatuck State Park. The corridor was originally a spur off the Old Colony...
 MA 1.6 mi Asphalt, 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
The World War II Veterans Memorial Trail opened in Mansfield in 2004 after several decades of advocacy by local rail-trail supporters. The trail rests on an abandoned corridor once served by the Old...
 MA 1.5 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...

North Bank Bridge

MA - 0.5 miles

The North Bank Bridge, which opened in 2012, provides a safe and convenient pedestrian and bicycle connection between Cambridge's North Point Park and Paul Revere Park in Charlestown. Spanning 690...

Charles River Bike Path

MA - 22.9 miles

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...

West Foss Farm Trail

NH - 1.6 miles

The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...

Accordion

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...

South Bay Harbor Trail

MA - 3.8 miles

The South Bay Harbor Trail connects several Boston neighborhoods—Lower Roxbury, the South End, Chinatown, and Fort Point Channel—to the Boston Harbor. The trail spans nearly 4 miles from Ruggles...

Heritage Trail (Manchester)

NH - 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...

Upper Charles Trail

MA - 13.2 miles

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,...

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...

Watertown-Cambridge Greenway

MA - 0.7 miles

The Watertown-Cambridge Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The trail begins in a busy shopping area on the site of a former U.S. Army arsenal. Trees...

World War II Veterans Memorial Trail

MA - 1.5 miles

The World War II Veterans Memorial Trail opened in Mansfield in 2004 after several decades of advocacy by local rail-trail supporters. The trail rests on an abandoned corridor once served by the Old...

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...

Stillwater Scenic Walkway

RI - 1 miles

The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...

East Boston Greenway

MA - 2.8 miles

More and more, airport lands near previously under-used rail corridors are being transformed from largely neglected vacant lands into urban greenways. These new vibrant spaces are used not only by...

Salisbury Point Ghost Trail

MA - 1.8 miles

Currently 1.8 miles, the Salisbury Point Ghost Trail provides a peaceful walk or bike ride through the woods on a well-maintained stone-dust trail. The route is one part of the larger Coastal Trails...

East Bay Bike Path

RI - 14.3 miles

With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...

Tri-Community Greenway

MA - 6.6 miles

The Tri-Community Greenway follows the route of the Boston and Lowell Railroad and its Stoneham Branch, originally built to serve Stoneham’s shoe factories and provide passenger service. The trail...

South Manchester Rail Trail

NH - 0.89 miles

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...

Peanut Trail

NH - 1.5 miles

The Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...

Salisbury Beach State Reservation Trail

MA - 0.6 miles

Although less than a mile, the trail running through Salisbury Beach State Reservation offers lovely views of the beaches off the northeastern coast of Massachusetts, just a few miles south of the New...

More Winchester bike trailsView Fewer Winchester bike trails

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...

Jay McLaren Memorial Trail

MA - 2 miles

Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...

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...

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...

Accordion

Blackstone River Greenway

MA,RI - 26.6 miles

Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...

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...

Nashua Heritage Rail-Trail

NH - 1.3 miles

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...

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...

Heritage Trail (Manchester)

NH - 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...

Ten Mile River Greenway

RI - 3 miles

Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...

Clipper City Rail Trail & Harborwalk

MA - 3.9 miles

The Clipper City Rail Trail is part of the Coastal Trails Coalition, which is developing in the four towns of Amesbury, Newbury, Newburyport, and Salisbury along the Merrimack River and will...

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...

Derry Rail Trail

NH - 3.6 miles

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,...

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...

Assabet River Rail Trail

MA - 8.6 miles

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...

Pine Tree Brook / Popes Pond Path

MA - 2 miles

The Pine Tree Brook Trail travels alongside the brook in Milton, Massachusetts. The path travels through woods and residential neighborhoods for a distance of about 1.8 miles, and it connects to the...

South Spencer Rail Trail

MA - 1.62 miles

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...

Neponset River Greenway

MA - 8.2 miles

The Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...

South Manchester Rail Trail

NH - 0.89 miles

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...

Old Railroad Trail

NH - 2.7 miles

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...

More Winchester walking trails View Fewer Winchester walking trails

Stillwater Scenic Walkway

RI - 1 miles

The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...

Watertown-Cambridge Greenway

MA - 0.7 miles

The Watertown-Cambridge Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The trail begins in a busy shopping area on the site of a former U.S. Army arsenal. Trees...

Bridle Trail

MA - 3 miles

Marshfield's Bridle Trail follows a former railroad bed through a tree-lined corridor. It begins at the town's Dandelion Park and heads north. Its compacted dirt surface is best suited for walking,...

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...

Accordion

Derry Rail Trail

NH - 3.6 miles

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,...

Roland Bergeron Bike Path

NH - 6 miles

The Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...

Pine Tree Brook / Popes Pond Path

MA - 2 miles

The Pine Tree Brook Trail travels alongside the brook in Milton, Massachusetts. The path travels through woods and residential neighborhoods for a distance of about 1.8 miles, and it connects to the...

Neponset River Greenway

MA - 8.2 miles

The Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...

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...

Border to Boston Trail

MA - 10.7 miles

The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...

North Bank Bridge

MA - 0.5 miles

The North Bank Bridge, which opened in 2012, provides a safe and convenient pedestrian and bicycle connection between Cambridge's North Point Park and Paul Revere Park in Charlestown. Spanning 690...

Heritage Trail (Manchester)

NH - 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...

Tri-Community Greenway

MA - 6.6 miles

The Tri-Community Greenway follows the route of the Boston and Lowell Railroad and its Stoneham Branch, originally built to serve Stoneham’s shoe factories and provide passenger service. The trail...

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...

Salisbury Rail Trail Connector

MA - 0.3 miles

The Salisbury Rail Trail Connector, also known as the Gillis Rail Trail Connector, is a 0.3-mile link between two rail-trails: Salisbury's Old Eastern Marsh Trail and Newburyport's Clipper City Rail...

Independence Greenway

MA - 5.3 miles

The 5.3-mile Independence Greenway makes for a pleasant ride, providing access to lakes, parks, and nature preserves. The paved pathway is located in the town of Peabody (pronounced by locals as...

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...

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...

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...

Gloria Braunhardt Bike Path

MA - 1.2 miles

Although short, the scenic Gloria Braunhardt Bike Path travels through forests and pastures full of birds and wildlife. The asphalt pathway parallels the eastern side of the present-day Interstate 95...

More Winchester running trailsView Fewer Winchester running trails

Recent Trail Reviews

South Bay Harbor Trail

I can't speak for the entire length of the trail, but the part by Melnea Cass Blvd is definitely unkempt. Cracks and bumps all along the pavement!

October, 2020 by thetigersteeth

I can't speak for the entire length of the trail, but the part by Melnea Cass Blvd is definitely unkempt. Cracks and bumps all along the pavement!

read more …

Upper Charles Trail

great trail

October, 2020 by glo1196

Flat surface with a places you can sit if need be. Beautiful this time of year.(OCT) can’t wait to explore the rest! Great for families, bikes and walkers.

read more …

Heritage Trail (Manchester)

Absolutely gorgeous views for autumn folliage! Very easy. We went up via road bikes, parking at the West Side Ice Arena. Easy to navigate, only wish is that it was longer!

October, 2020 by thelovelylynette

Absolutely gorgeous views for autumn folliage! Very easy. We went up via road bikes, parking at the West Side Ice Arena. Easy to navigate, only wish is that it was longer!

read more …
Accordion

World War II Veterans Memorial Trail

Great paved trail. Perfect for strollers. It's really about 2 miles each way. Very nice scenery with trees on each side. There is a little bit of parking at the end of Cobb st. Otherwise I would say you can park near the town hall.

October, 2020 by chabba99

Great paved trail. Perfect for strollers. It's really about 2 miles each way. Very nice scenery with trees on each side. There is a little bit of parking at the end of Cobb st. Otherwise I would say you can park near the town hall.

read more …

Roland Bergeron Bike Path

beautiful

October, 2020 by elanawells7

This trail is perfect for riding your bike through the woods, fun and scenic!

read more …

Upper Charles Trail

Excellent trail

October, 2020 by mendezmartin

Excellent condition, beautiful landscapes, bridges and tunnels - this trail is amongst the very best we’ve done. Good for any level, from family riding to faster-type work-out. Highly recommended.

read more …

Upper Charles Trail

Upper Charles on my bike

October, 2020 by kneec423

This was my first time on this trail, despite driving by it more times than I can count. What a wonderful ride. Mostly flat, but some low grade rises. Can’t wait to come back again- maybe tomorrow!

read more …

Southwest Corridor Park (Pierre Lallement Bike Path)

biking boston

October, 2020 by lraciukaitis

This is an amazing option for commuters in Boston and bikers trying to get from point A to point B in the city. The bumpy and cracked pavement made it difficult to enjoy as a leisurely ride.

read more …

Nashua River Rail Trail

Nice trail

October, 2020 by italy2

Started in Nashua 1st time doing this trail and i have to say we loved it. Loved the little town of Pepperell while biking thru and continued to Groton.
Love the scenery and nature. We will be going back again.

read more …

Clipper City Rail Trail & Harborwalk

Learned about it from a friend ¿¿

October, 2020 by c17cacheryl

I’m learning/exploring lots of fabulous new to me places close to home and today’s walk was a treat!

read more …

Martin H. Burns Wildlife Management Area Trail

Cycling from Highfield Rd. to Newburyport Railroad Terminal

October, 2020 by OliverJones

I use the segment from Highfield Road to the train terminal a lot, on a road bike. It has a power line above it.

It's cinders. The surface is mostly good, with a couple of spots of loose sand. Vegetation is gradually reclaiming the old railroad bed.

TREACHEROUS in heavy rain. Deep puddles. Be careful!

read more …

Salem-Beverly Canal Path (Grand Wenham Canal Path)

Gand Wenham Canal Trail

September, 2020 by jordan37

I tried to ride on this trail. It’s apparently closed.

read more …
View more reviewsView fewer reviews

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