Explore the best rated trails in Dudley, MA. Whether you're looking for an easy walking trail or a bike trail like the Fresh Pond Bikeway and Upper Charles Trail. With more than 82 trails covering 593 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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The Cochituate Rail Trail (CRT) is a multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. The segment in Framingham was completed and...
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 well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
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 Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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 Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
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 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...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
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...
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
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 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 Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
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 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 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,...
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
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 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 Squannacook River Rail Trail is presently 1.1 miles long, from Depot St. to Old Meetinghouse Road in Townsend, Massachusetts. The trail occupies the Greenville Branch of the Boston and Maine...
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
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...
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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 Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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...
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
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...
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers 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 Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
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,...
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 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 unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
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 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 Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...
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 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 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...
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 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 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 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 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...
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...
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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!
Although this trail is not that long, it make a nice addition to riding the Vernon trail. It's a nice quiet ride and a must to experience.
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.
Went from Keene to Troy Depot, passable, but very rocky, muddy and barely passable with a hybrid bike. Finding the trail out of Keene wasn't obvious - finding and following the blue diamonds on the trees helped. Crossing rte 101 is pretty dangerous. Toward Troy, there's a lot of what appears to be snowmobile trail maintenance going on making the trail difficult for biking, again dislodged rocks and lots of mud. Left Troy going to Fitzwilliam and the trail became unpassable with my wife's hybrid and difficult on my mountain e-bike. Big time wash-out on the trail that goes on forever. I recommend staying away from it at least this time of the year unless you like this kind of mountain biking...
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.
If you park in Bolton State Park to start on the east end of the Charter Oak Greenway you won’t find any markings for the entrance. It actually starts right at the RT44 West highway entrance to the park. So you need to go down into the lot to park and then go back up the entrance ramp to find the beginning of the Charter Oak Greenway, which is not even marked as such though.
Also fair warning to older riders I only went the first five miles west but that portion at least has very little flat areas, almost all of it is uphill or downhill. Heading west, mostly downhill, but heading back east mostly uphill, including one extended relatively steep climb. No problem for younger riders or riders in great biking shape, but pretty difficult for a casual rider.
On the plus side that portion of the trail at least is very well paved with virtually no divots or surface cracks.
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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