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 77 trails covering 355 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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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 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...
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...
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...
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...
The Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...
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...
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...
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 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...
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...
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...
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...
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...
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...
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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,...
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...
The Old Eastern Marsh Trail (a.k.a the Salisbury Rail Trail) runs for over 3.5 miles between the north bank of the Merrimack River and the New Hampshire state line, north of Salisbury. The beautifully...
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...
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 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 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...
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 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...
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 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...
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 Old Eastern Marsh Trail (a.k.a the Salisbury Rail Trail) runs for over 3.5 miles between the north bank of the Merrimack River and the New Hampshire state line, north of Salisbury. The beautifully...
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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...
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 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...
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...
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...
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 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 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 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 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...
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,...
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...
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...
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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...
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 Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...
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 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 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...
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...
Currently just over two miles long, the Salisbury Point Ghost Trail provides a peaceful walk or bike ride through the woods on a well-maintained stone-dust trail. A paved extension was constructed in...
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 Swampscott Rail Trail is a developing rail-trail in the North Shore community of Swampscott. The trail, when complete will extend two miles through the heart of the town ending with a seamless...
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...
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...
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...
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...
The Garrison Trail is a two-lane, paved, hike-and-bike path that runs alongside I-95. The trail stretches 1.8 miles between State Route 113 in Newburyport and State Route 110 at the Amesbury-Salisbury...
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 Old Eastern Marsh Trail (a.k.a the Salisbury Rail Trail) runs for over 3.5 miles between the north bank of the Merrimack River and the New Hampshire state line, north of Salisbury. The beautifully...
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,...
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,...
So wonderful to discover this beautiful trail on a recent trip back home from California. What a pleasure to walk where before we only glimpsed these views passing by in the car from Route 9 or 30. I easily found a few various entry points by using Google Maps and was delighted with the gorgeous fall views. Most of the path had some nearby water features whether it was Lake Cochituate or a smaller stream. The path was well maintained and we enjoyed the feeling of being far removed from the hustle and traffic of the rest of the busy area, What a gift to the community!
I've done trails over over and over again in one day it's tiring but worth it. (The Ten Year Old Girl Who Dreams Of Being One Of The Best Bikers But Not To Be Famous)
Now that I've ridden this connector trail, I believe the description is a bit misleading. This trail connects directly with the Old Eastern Marsh Trail, runs under the north end of the Route 1 bridge from one side to the other, and connects to a sidewalk that enables one to then cross the drawbridge. This sidewalk is not suitable for cycling. Once across to the south side, the sidewalk there meets the Harbor Walk and Clipper City trails. This trail enables one to cross under Route 1 avoiding the actual Route 1 traffic - enjoying the art and river view on the way.
Since our last visit here the bridge north of Holliston has been paved and beautiful railings with info signage. A 12 foot wide hard packed stone trail with breathtaking views. The town deserves two thumbs up! The trail head at Holliston has been really spruced up with a coffee shop/bakery across the street and a railroad depot dinner with paved parking.Small parking area at Whitney street. The entire trail all the way is a gem.
What a great way to experience the fall foliage!
Great walk along the riverside. Mostly level, flat and paved surface. Easy walking and quite quiet for a Saturday. Great day for a walk along the river.
We started at airport and went out 2.5 miles and then turned around. Easy path, smells wonderful, leaf changing colors breathtaking! We loved the scannable QR codes that teach you along the way about plants, trees, sites etc. we learned quote apt!
This has moved to my favorite trail. I can’t wait until the extension is open. Very nicely maintained and people are friendly. Road passing were great with all flashing lights a vehicles stopping early. This is a nice ride.
Went in fall, came from central mass. Not a huge fan of this trail on my trail bike, maybe on a mountain bike. badly maintained and narrow, lots of tree roots. But parking was super easy since its near a business park.
Came out from central mass and it really wasnt what i was expecting. Might be fun if you have a mountain bike but this is more of a local's spot for daily exercise
Rented ebikes from Pedigo nearby trailhead and Rachel and Ed were so nice. The trail was cold and shaded a good part of the ride so bring layers. We brought a picnic, plenty of places to stop and eat. The trail is somewhat confusing at the end so we just decided to turn around and head back. Great day all and all!
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