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 607 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 Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
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 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 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 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,...
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 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 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...
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 Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
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 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...
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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...
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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 50 miles from Boston to Northampton...
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 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 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 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...
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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...
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...
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...
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 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 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...
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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 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 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 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 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 50 miles from Boston to Northampton...
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
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...
The Phenix-Harris Riverwalk, a short trail built on a former rail bed purchased from Penn Central Railroad, connects West Warwick and Coventry, two towns on the outskirts of Providence. The dirt...
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
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 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...
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 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 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...
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...
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...
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 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...
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...
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 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 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...
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...
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 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...
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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 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,...
If you want a quick ride, this is your trail. Enjoy!
My wife and I rode our recumbent trikes on the entirety of this trail on a Saturday evening. For the most part, we encountered only walkers. And based on the surface condition of the trail, I understand why. The pavement has deteriorated and is full of root-bumps and small dips. It was a very rough ride.
I would recommend this trail for walkers, joggers, or cyclists if you've got a bike/trike with a suspension. The bulk of the trail is on the old towpath between the river and the canal, so other than the north and south ends, you are separated by water from the rest of the world. This makes for a quiet, relaxing, and scenic trek. The northern terminus near the parking lot, which also forms a "T" with the CT 190 bridge, and the southern terminus by the renovated mill building are new and in great shape. All we need now is for Connecticut to resurface the original portion... even stone dust would be better than the broken pavement.
We continued on to the MA/NH line and connected to Cheshire Trail to Keene, switched to Ashuelot and connected to The Fort Hill in Hinsdale, NH. Gardner to Brattleboro via Keene! All good trails.
I went here on a beautiful Sunday afternoon. What a lovely place! This is a paved trail that follows the river and has a nice playground and picnic area at one end. There are various sculptures related to Abraham Lincoln along the way. It was very relaxing to stroll along the water. The views of the bridges and the Hartford skyline are stunning. Will definitely return!
Encountered a closure north from Hurricane Rd. Not sure how far, but sign says until the end of June. Unfortunately my favorite section!
One of the best ways to see Boston in a green space amidst all the concrete. There are several traffic light/cross walks that interrupt the complete journey but are very easily accessible by foot, bike, wheelchair and stroller. Stop to enjoy some of the signage to see what local/indigenous flowers have been planted.
This path extends around the entire reservoir bridging Cambridge & Belmont. It's a lovely 1hour walk, with or without dogs. Sometimes a bit crowded, has a muddy/mulched section which can make ADA/stroller use a challenge, but otherwise lovely. Enjoy!
On e Bikes; trail to north from Windham generally passable but long wet areas (eventually turned around) and trail a bit rougher than going south from Willimantic. The south trail is in much better shape and had inviting scenery with streams, farms and wetlands/lakes + virtually no wet areas on trail. Went to RT 87 (about 8 miles) from Willimantic. Plan to do this again and go further.
Good trail, nice but it is 4-5 miles of asphalt. If anyone knows were it extends to LMK.
Great trail and very scenic. All paved and pavement in very good shape. Parked at lot on New Britain Ave. and went NW to Collinsville and then to Rte. 44 in Canton. Then rode trail back to start.
10 miles each way. Very enjoyable journey. 90%+ of ride is on nice wide trail. First half of trip is constant, gentle up gradient. Ride back about 60% faster since going mostly gently downhill along river.
Parked at lot on Railroad St off of 44. New parking lot and pavilion with new overpass for trail over main road. Took trail NE to Town Farm Rd. and then streets into Putnam. Trail in this section gets average rating of 2+. Trail base is coarse rock (1.5" +) with washed out ruts. Somewhat bumpy ride. Only good for bikes with wider tires. In Putnam went south on Putnam River Trail (excellent paved trail) south to bridge over Quinebaug River. Crossed river climbed up steep hill to get to old rail trail and took this back to starting point.
Next went SW from rail station on trail to Covell Road. This section of trail in very good shape. Hard packed gravel base. I'd rate this a 4. Easy going for most bikes.
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