Explore the best rated trails in Medway, 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 94 trails covering 526 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 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 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 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 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 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 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 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 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 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 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 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 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...
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 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...
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 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 pleasantly tree-lined Warren Bike Path, built along the former Warren-Fall River Railroad, runs just under a mile from Long Road west to the Kickemuit River. The trail ends in an 18-acre park...
The URI (University of Rhode Island) Bike Path provides a safe conduit for students, faculty and staff to commute to and from school via the William C. O'Neill Bike Path. The asphalt, two-lane 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...
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 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 overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
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 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 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...
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...
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...
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,...
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
Riverpoint Park sits nestled into a bend of the Pawtuxet River in West Warwick, Rhode Island. The park accommodates the 400-ft arboretum which leads to 1.3-mile riverside path known as the Senator...
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...
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 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 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...
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 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 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 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 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 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,...
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...
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
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 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 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....
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
The New Bedford Covewalk, like the HarborWalk further east, sits atop the hurricane barrier built to protect New Bedford residents from storm surges during extreme weather. Even when it's nice out...
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 Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
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...
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 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 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...
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 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...
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,...
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The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
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...
What a great way to experience the fall foliage!
I drove to find this trail two times and could not find where it begins or where to park. I'm glad for those who love it, but in using both the map and GPS, I can not find it??
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!
This trail has been extended from the Howe School eastward crossing Webb St., ending at Maple Street. The surface on the western section is nicely compacted, the eastern section, not so much. And the Webb Street crossing is pretty rocky & washed out. It is still under construction but useable. Would be a great place for a kid learning to ride a mountain bike on a rough surface. Pretty straight, flat, and quiet.
Easy trail, lots of shade, first time to try pedigo bikes in Salem
On a Sunny Afternoon 70 degrees this is a great walk, especially the bridge over the Pope’s Pond outlet which was rushing over he dam and the trees were changing color. Made for a pretty picture of my wife. A note to those who want to walk from the Lafayette Street entrance to Thatcher, you need to cross the bridge at Milton High School and continue the path on the other side of Pine Tree Brook along the brook to Thatcher Street. There are paths on both sides; one goes into the Audubon Road neighborhood, the path on the other side goes to Thatcher. Path has been maintained and wood chips along the way cut down on mud and erosion addin to an enjoyable walk on a Fall Afternoon. Thanks for including it on your list. Lived here 45 years and didn’t know it existed.
Though a little confusing to navigate this is a very nice trail. All paved on the Quincy side. Gets a little strange in the Milton side. There is plenty to see and is kinda a quick ride, but fun.
Have walked the entire trail from Saxonville to Natick, as far as it goes. It’s a great trail, but clearly a work in progress. The Framingham side has no signs, and it took us several tries before we found it (just to the right of the fire station). The Natick side is complete as far as it goes, but it stops abruptly in the woods. Also along the length there are no designated parking areas.
No toilet facilities on / near India Point Park. Closest is Haines S.P. a few miles down the trail. The signs could be a little clearer on how to get over the river to connect to the main trail. The 2 wooden bridges down the trail were closed but, detours were easy to navigate. In Bristol look for the small building on the road which is a toilet. Many places to eat.
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