Explore the best rated trails in Gloucester, 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 76 trails covering 348 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.
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...
The Middleton Rail Trail is a trail project along the former Essex Railroad. When complete, the trail will stretch 4.5 miles through the town, and perhaps join the Danvers Rail Trail. Phase I of the...
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...
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...
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...
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...
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...
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...
The Chelsea Greenway was built to accompany the extension of the Silver Line between Boston and its northern suburb, Chelsea. The asphalt multiuse trail begins at the Eastern Avenue MBTA station and...
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...
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...
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...
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...
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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,...
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...
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...
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...
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...
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...
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...
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...
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...
The Middleton Rail Trail is a trail project along the former Essex Railroad. When complete, the trail will stretch 4.5 miles through the town, and perhaps join the Danvers Rail Trail. Phase I of the...
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...
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...
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...
The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...
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...
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...
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...
Constructed in 1967, the Province Lands Bike Trail is the first bike trail ever built by the National Park Service. The trail, located at the northern tip of Cape Cod, features steep hills, sharp...
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...
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...
The Chelsea Greenway was built to accompany the extension of the Silver Line between Boston and its northern suburb, Chelsea. The asphalt multiuse trail begins at the Eastern Avenue MBTA station and...
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...
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...
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...
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...
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...
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...
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...
The Middleton Rail Trail is a trail project along the former Essex Railroad. When complete, the trail will stretch 4.5 miles through the town, and perhaps join the Danvers Rail Trail. Phase I of the...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
The Chelsea Greenway was built to accompany the extension of the Silver Line between Boston and its northern suburb, Chelsea. The asphalt multiuse trail begins at the Eastern Avenue MBTA station and...
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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...
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...
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...
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...
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...
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...
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,...
Its a very nice clean and smooth bike path great for scootering rollerblading and biking. We really enjoyed it. They have some park bench and trash barrels which are always appreciated!
This trail is closed due to construction. The asphalt is broken up into sections exposing the dirt
We found the trail while walking around town-great find!!
Quiet, hidden trail. No obstructions and could navigate well on snowpacked gravel trail. Was a relaxing walk as there were no unleashed dogs or unmasked people.
I've noticed some criticism of this trail that I think would be unfair. It's clearly not among the most enjoyable if one compares it to riding the Battle Road Trail, but it's conveniently located. I know these trails closer to cities with higher population are most often paved, but this would be superb if it were dirt. I love the rocky section and the section closer to Lynn that's still dirt, ironically the parts that receives the most criticism.
When you want to ride your bike, and you're close to the Everett area, this trail provides a path half way to Salem MA without having to bike streets that aren't very "bike friendly".
The southern sections I agree aren't the greatest of scenery and there are a few street crossings, but there are some relatively peaceful areas on that section. And the northern half has some wonderful areas surrounded by trees. Call me an optimist but I can't complain about minor details of a path that's in a location that really needed a path for cyclists. I heard a rumor that it's going to be extended soon--a path that took us closer to Salem or Peabody would be ideal, but it's incredibly handy and I live nearby it. I've never seen it crowded or have high traffic. There are quite a few stops on the south section if you need a store or to avoid some bike-commuter street traffic in the Everett to Malden areas, so what's NOT to like.
My friends and I ride hardtails through there and really do enjoy it. I'd prefer a dirt trail instead, one more friendly to a full sus' frame, but for that it gets only 4-stars from me lol! ANY trails/paths in these more populated cities are HIGHLY welcomed and speaking for myself, sincerely appreciated. Ride it the FULL distance south to north (it's short, like 8 miles) and see how you'll enjoy it even more if you haven't ventured to the northern half. At the traffic intersections just be careful, which isn't a big deal for someone like myself that bikes through Boston all the time.
~JSV
If you are using a manual or electric wheelchair, park at the Fruit Street entrance (airport end). If you park in the municipal lot, you will need to cross a busy street and go over a small patch of grass/gravel to get to the path. This trail is flat, smooth, and the people (and their dogs) are friendly!
The portion of the trial from I-95 to Hayfield St has substantially degraded for cyclists. A small portion of trail floods for a good portion of the summer (thank you beavers!). The flooded portions can be walked around.
New in 2020 are sand and rock obstructions in which your tires sink and it is impossible to continue pedaling without walking a bit. Maintenance on this trail is sufficient for vehicles, walkers and the utilities, but my mountain-style bike struggles.
It is an interesting trail otherwise in the middle of know-where. Pity.
My husband and I rode the Upper Charles Trail from the Hopkinton start to the near end in Holliston this last Saturday in November 2020. What a pleasant surprise! We enjoyed very pretty scenery in Hopkinton, a great lunch at Oliva's Market in Milford, visited the brand new Boston Honey Company store in Holliston, and marveled at the historic Phipps Railroad Tunnel under Highland Street. The trail changes from asphalt to very rideable stonedust in Holliston. At just over 13 miles one-way, the trail is a great way to enjoy being outside and getting some great exercise to boot! I thoroughly recommend this trail to anyone who likes pretty scenery, and great stops along the way.
Consider this a great way to travel between two lovely towns rather than a picturesque trail with stunning views all the way. However take in a great view from the end of the bay at the Lead Mines area. In summer hundreds of fishing and pleasure boats are moored between the towns of Salem and Marblehead . If ,coming from Salem , you take the right spur to Swampscott the trail ends and there isn’t much to see like there is in Marblehead or Salem. In Marblehead make sure you visit the old fort and gun battery .
Where this trail starts in downtown Nashua is not a great area. We biked it recently to get access to the Mine Falls Park. About half way down the trail is better but would probably have to park on a street. If you are looking for a nice bike ride I suggest the Nashua River trail. Mine Falls is nice but you are in the minority if you are biking. There are a lot of walkers.
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