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 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 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 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...
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 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 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...
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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...
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 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...
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...
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 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 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 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...
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 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...
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,...
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 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...
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 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...
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...
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 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...
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,...
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...
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...
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...
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 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...
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 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 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...
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 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 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 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 Head of the Meadow Trail offers a pleasant winding route through woodlands and marshlands tantalizingly close to the Atlantic Ocean in Truro. In fact, direct access to two of the Cape Cod National...
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...
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 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 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...
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...
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 Head of the Meadow Trail offers a pleasant winding route through woodlands and marshlands tantalizingly close to the Atlantic Ocean in Truro. In fact, direct access to two of the Cape Cod National...
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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...
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...
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 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...
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,...
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 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...
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 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 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...
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 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 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...
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 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...
Not sure why this particular trail gets top reviews. Maybe for walking and scenery. I'll give it that but for biking it sucks. The entire paved trail is nothing but divots and tree roots trying to break through the surface. I found it impossible to bike any short distance without hitting a marked or unmarked divot and when not hitting one of those a tree root. I hit numerous imperfections at 20+mph (no one around at the time) and almost got knocked off the bike. Thumbs UP for walking, dumbs DOWN for biking.
Ran the length of the trail to set up a Fastest Known Time segment. Was surprised by how beautiful the whole trail was, and how much the flora changed throughout. Id like to go back at a slower pace and stop at some of the towns it crosses (like Raymond and Epping)
The paved and complete section is 2.0 miles long from the Windham Rail Trail to the Salem Main Street Depot. The next 1.3 miles are under development with CMAQ grants helping. The remaining distance to Methuen is not complete or funded but passable on a regrind surface. This 5.2 mile Salem corridor is the south link of the Granite State Rail Trail. (Submitted by Dave Topham, FSBPC Co-Chair & Treasurer)
I ran 8 miles of the trail and it was perfect! Lots of shade, mostly flat and all paved. Around mile 1 you have to pay attention to where the trail goes since you cross a street but other than that everything is clearly marked. I felt safe and there were even porta potties along the run at certain mile markers. Didn’t use them, but it could come in handy one day! Lovely trail for runners, bikers and walkers of all ages. Definitely coming back again!
This is locally known as the Danvers Rail Trail, runs through Hamilton, then Topsfield, until it ends at I-95. Nice crushed stone from Danvers north, packed stone south, packed dirt in Topsfield. Sides of the trail near marshland are covered with poison ivy spring and summer. big roads with lights at 62, 97 (twice) route a joy to ride. Forest, water
I only started riding this trail this year and after primarily riding rail trails I found it a refreshing challenge. It varies in elevation so it is more challenging than say a Londonderry or Derry. However the best part is that it is MUCH less crowded! I tend to go here on the weekends simply because there won’t be nearly as many people on it. There are a few places to park along the trail, but I recommend the fire station or school. It is not the most scenic ride (it is not bad by any means but not as good as other trails), but the challenge and convenience factors rate it high in my book.
This trail goes along a road, through residential areas and by a couple of parks. It's very safe with some road crossings. It's a bit confusing because the bike path continues after the "End" sign. If you're particularly looking for a scenic ride, this isn't it. However, it's the perfect trail for commuting or to go back and forth on to put in some miles.
Nice trail, well maintained. Seamless connection to Windham and Derry trails
We rode the entire trail, and the construction is finished. The trail was open the entire way. Wide, smooth, beautiful trail
I love this trail, well maintained easy to ride and friendly people along the way. Thou I have not completed the entire trail, it’s definitely on my list of riding goals.
I have not done the whole trail, but for an out of town cyclist, the section from the train station to fisher street is a stress free option to the narrow, crowded roads of Dover.
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