Explore the best rated trails in Brookline, 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 100 trails covering 559 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 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...
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 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...
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 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 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 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...
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...
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...
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...
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...
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...
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...
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...
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 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...
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 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 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...
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 Phoenix Bike Trail cruises through a mixture of surroundings on its relatively short 4-mile journey from the heart of the historical Fairhaven seaport to woodlands and farms on the outskirts of...
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 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...
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 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 West Warwick Riverwalk is located in a park just behind West Warwick High School and John F. Deering Middle School. The paved trail goes for about a mile north following the Pawtuxet River. A...
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....
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 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 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...
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...
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 Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
The Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...
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 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 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...
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...
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 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 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...
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...
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...
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...
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 Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
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 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 Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...
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...
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 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 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 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...
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...
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...
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 Mason Railroad Trail runs for nearly 7 miles from near the New HampshireMassachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
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...