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 73 trails covering 568 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 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...
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 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 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 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 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...
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 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...
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...
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 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 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 Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
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,...
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 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 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 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...
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...
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 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 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 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....
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...
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...
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 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 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...
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 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 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 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 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 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...
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 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...
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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,...
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 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 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 Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
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 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 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 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...
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 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...
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 Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
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,...
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 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,...
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 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...
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 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...
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 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...
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...
Now the Cochituate Rail Trail has more than doubled in length stretching from Saxonville to Natick ad going past Lake Cochituate alongside North Main St (Rte 27). Railroad Whistle monuments along the way and many benches and bicycle rings for a brief respite.
I'm reviewing the Southwick Rail Trail and Colombia Greenway Trail together as I rode up from the Farmington Canal trail and didn't see where one ended and the other began.
The two trials are smooth, relatively scenic, well-marked, avoid too many road crossings (especially nice when in a neighborhood), and are a pleasant ride for any skill level.
On its own, the Colombia Greenway trail might be a little short but it connects seamlessly to the Colombia Greenway Trail, and then to the Farmington Canal trail, that is not as much of an issue.
I wish I could give this 4.5 stars.
It is really two separate trails with a five-mile gap. I rode both sections. The bottom section was slightly nicer and might have squeaked out 5 stars on its own.
Most of the trail is shady and scenic. the pavement is generally smooth but a few roots. However, in the northern section it is not really well-marked and a bunch of times I needed to pull out my GPS, either to guess which way to go at a fork or as the poor marking meant I went off trail. The lower section has a part in northern New Haven where it is not kept up as well and there are lots of road crossings.
The trail is relatively long, is scenic, manages to avoid too many road crossings, is easy to follow without getting confused, doesn't have a ton of cracks in the pavement, keeps crowds relatively low (I rode it on Labor Day) so you aren't stopping every 5 minutes, etc.
I really felt like I could glide along peacefully at a good clip.
The only slight issue was there are a few roots under the pavement that have broken it making mini speed bumps.
Once we got to the Sanitation site north of Keene the trail wasn't more then a goat trail. Muddy, rocky narrow, and not very much fun. We turned around. Maybe it would be better from Walpole south.
This might be one of my new favorites. Clean paths, Nice crossings, Plenty of places to rest. There is only one bumpy area on the hole trail. Small complaint: the parking directions need to be updated. The office building is called Cross Point and the highway exits have changed. Otherwise , this is a nice way to spend an afternoon .
We had a delightful mid-Labor Day ride, with warm sunshine and many others the closer we went from Readville to John Paul Park, and then few again as we returned to our car. The southern portion along Truman Parkway, mostly on sidewalks, was our least favorite, and I think we’d park at the Neponset Esplanade Park next time, and brave further north to the JFK Museum, and beyond?.
Southern section very rough, significant ATV use (officially sanctioned). Washed out slopes can be unsafe with large cobbles, exposed bedrock, and washouts. If you manage to escape the ATVs it's quiet.
Very convenient trail that runs along 384 up though Bolton. Three beautiful bridges cross brooks below. Trees and valley views add to the ambiance. Highly recommend for a fairly easy bike ride.
I’m from nyc so I LOVE walking and this park is definitely one of my top favorites! It’s not only the cleanest park, it’s also one of the most interesting and fun parks I’ve been to! The playgrounds are awesome! The view is incredible, it isn’t uphill, so it’s a steady paced path and it’s simply magical! Plus my dogs love it and dogs are welcomed!
It's a great trail and it would be good to have a map of it but this site is missing quite a bit of the trail.
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