Explore the best rated trails in Southbridge, MA. Whether you're looking for an easy walking trail or a bike trail like the Upper Charles Trail and Minuteman Commuter Bikeway. With more than 72 trails covering 567 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 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 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 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...
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...
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 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...
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...
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
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 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 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 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 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...
Quonset Point Bike Path is a fantastic two and a half mile trail. The Quonset Point Bike Path is a part of the beautiful town of North Kingstown.The Quonset Point Bike Path is paved and off road and...
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...
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...
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 Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
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 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...
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 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 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 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...
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 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 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 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...
Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...
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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 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...
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 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 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 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 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...
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 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...
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....
Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...
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...
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 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...
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 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 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...
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...
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 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...
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 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...
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 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 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...
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...
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...
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...
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 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...
I was pleasantly surprised that trail had been repaved or at least repaired. Most of the tree limbs and frost heaves are now gone. Pretty ride made better by surface upgrade - thanks
Was excited to try this trail for inline skating. We started in Waltham and loved the beginning but we hit a section that was entirely dirt pretty quickly and had to turn back. I’m sure it’s beautiful for bike riding.
Beautiful trails to skate, lots of pebbles near intersections but otherwise clean and smooth.
Very smooth and safe. Great with kids and beginners. Lots of trees and not too crowded. Highly recommended.
Rode 7 miles out and then back. Beautiful area. Really good workout. Few hills. But nice quiet area midweek
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
Very pretty, well kept, no one else there in the middle of a sunny spring day!
Parked and road the trail from Fino Field in Milford. No usable facilities at the field likely due to Covid. The trail is mostly level with small grades in parts. It passes through urban, residential and forested areas. The surface is paved to the Milford line on both legs, where it then becomes hard packed process stone. Road bikes (25 mm tires) can negotiate the trail. The leg from Fino Field to Holliston is about 9.5 miles to the unimproved section, which had considerable standing water preventing further exploration. The trail passes through Holliston at the 7.5 mile mark where there are some small eateries and a town greenspace. Phipps Tunnel is noteworthy. The leg from Fino Field to Hopkington is about 4 miles to the trail terminus. The trail passes through Louisa Lake Park (picnicing and fishing). Foundations from early granite cutting sheds served by the former Hopkington RR of the late 19th century are visible on the left near the terminus of this leg.
Good bike path. Easy to access for a short ride. I saw bridges, streams, old chocolate factory, the non-stop old metro trains. Not too crowded.
Wow! I was pleasantly surprised by all the lovely artwork along this trail. The river, falls, and arch are all so pretty. Glad I went exploring ¿¿¿¿¿
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