Explore the best rated trails in Winchester, 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 92 trails covering 535 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 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...
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...
Lowell's Canal System Trails are part of Lowell National Historical Park in Lowell, Massachusetts. The park preserves some of America's industrial past: its 19th-century textile mills formed the first...
The Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...
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 Clipper City Rail Trail is part of the Coastal Trails Coalition, which is developing in the four towns of Amesbury, Newbury, Newburyport, and Salisbury along the Merrimack River and will...
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 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 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 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 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 Middleton Rail Trail is a trail project along the former Essex Railroad. When complete, the trail will stretch 4.5 miles through the town, and perhaps join the Danvers Rail Trail. Phase I of the...
The Mystic River Greenway is part of the Mystic Greenways trail system, which also includes the Wellington Greenway and the Malden River Greenway. When completed, the trail will connect the...
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...
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
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...
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...
The Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...
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 South Manchester Rail Trail is a proposed bike/pedestrian path that would connect the downtown Millyard area of Manchester to the Town on Londonderry. The South Manchester Rail Trail will utilize...
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...
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...
The Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...
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The Heritage Trail is managed by the state of New Hampshire to provide access to recreational and historical attractions across the state. Eventually, the north-south route along the former Boston and...
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 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 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 Head’s Pond Trail (formerly known as Hooksett Rail Trail) is a 1.9-mile rail-trail that visits two scenic ponds, including the eponymous Head’s Pond, in a woodsy area of Hooksett. The trail’s...
In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...
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...
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 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...
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 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...
When complete, the Salem Bike-Ped Corridor will run for more than 5 miles on a former Boston and Maine Railroad corridor from connections with the Windham Rail Trail (north) and Methuen Rail Trail...
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 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...
The Boxford Rail Trail is a short, rustic pathway open on a former rail corridor in rural Essex County. Now home to overhead electric wires owned by National Grid, the trail is open via a license...
The North Bank Bridge, which opened in 2012, provides a safe and convenient pedestrian and bicycle connection between Cambridge's North Point Park and Paul Revere Park in Charlestown. Spanning 690...
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...
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The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...
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 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 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...
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 Head’s Pond Trail (formerly known as Hooksett Rail Trail) is a 1.9-mile rail-trail that visits two scenic ponds, including the eponymous Head’s Pond, in a woodsy area of Hooksett. The trail’s...
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...
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 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...
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...
Although less than a mile, the trail running through Salisbury Beach State Reservation offers lovely views of the beaches off the northeastern coast of Massachusetts, just a few miles south of the New...
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 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 Quarries Foot Path offers a wooded 1-mile hiking route in western Quincy, about 10 miles south of Boston. Begin your adventure on the south side of Ricciuti Drive, which borders Quincy Quarries...
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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,...
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
Quiet, hidden trail. No obstructions and could navigate well on snowpacked gravel trail. Was a relaxing walk as there were no unleashed dogs or unmasked people.
I've noticed some criticism of this trail that I think would be unfair. It's clearly not among the most enjoyable if one compares it to riding the Battle Road Trail, but it's conveniently located. I know these trails closer to cities with higher population are most often paved, but this would be superb if it were dirt. I love the rocky section and the section closer to Lynn that's still dirt, ironically the parts that receives the most criticism.
When you want to ride your bike, and you're close to the Everett area, this trail provides a path half way to Salem MA without having to bike streets that aren't very "bike friendly".
The southern sections I agree aren't the greatest of scenery and there are a few street crossings, but there are some relatively peaceful areas on that section. And the northern half has some wonderful areas surrounded by trees. Call me an optimist but I can't complain about minor details of a path that's in a location that really needed a path for cyclists. I heard a rumor that it's going to be extended soon--a path that took us closer to Salem or Peabody would be ideal, but it's incredibly handy and I live nearby it. I've never seen it crowded or have high traffic. There are quite a few stops on the south section if you need a store or to avoid some bike-commuter street traffic in the Everett to Malden areas, so what's NOT to like.
My friends and I ride hardtails through there and really do enjoy it. I'd prefer a dirt trail instead, one more friendly to a full sus' frame, but for that it gets only 4-stars from me lol! ANY trails/paths in these more populated cities are HIGHLY welcomed and speaking for myself, sincerely appreciated. Ride it the FULL distance south to north (it's short, like 8 miles) and see how you'll enjoy it even more if you haven't ventured to the northern half. At the traffic intersections just be careful, which isn't a big deal for someone like myself that bikes through Boston all the time.
~JSV
Great trail. Wonderful walk but, caution, it reads as 3 miles on the surface. It is actually 7. Once you read all the detail you see that 4 miles more through Brookline.
Parked in West Warwick next to rev dept tennis courts. Hopped on trail right there. Rode in direction toward Coventry. Interesting mix of residential, industrial, mills, rural areas. Clean, level and super fun.
The portion of the trial from I-95 to Hayfield St has substantially degraded for cyclists. A small portion of trail floods for a good portion of the summer (thank you beavers!). The flooded portions can be walked around.
New in 2020 are sand and rock obstructions in which your tires sink and it is impossible to continue pedaling without walking a bit. Maintenance on this trail is sufficient for vehicles, walkers and the utilities, but my mountain-style bike struggles.
It is an interesting trail otherwise in the middle of know-where. Pity.
My husband and I rode the Upper Charles Trail from the Hopkinton start to the near end in Holliston this last Saturday in November 2020. What a pleasant surprise! We enjoyed very pretty scenery in Hopkinton, a great lunch at Oliva's Market in Milford, visited the brand new Boston Honey Company store in Holliston, and marveled at the historic Phipps Railroad Tunnel under Highland Street. The trail changes from asphalt to very rideable stonedust in Holliston. At just over 13 miles one-way, the trail is a great way to enjoy being outside and getting some great exercise to boot! I thoroughly recommend this trail to anyone who likes pretty scenery, and great stops along the way.
Rode the eastern section of this trail from the parking lot at the end of Adams St in Uxbridge to Grove St in Franklin, approximately 11 miles. For the first 3.5 miles the trail is part of the Blackstone River Greenway and is in excellent condition with smooth blacktop surface. You'll see cyclists, skateboarders, runners and walkers on this section. The improved trail ends in Blackstone at Canal St. Follow Canal St downhill, make a left onto St Paul St, then right on Main St, and left into Castle Hill Way. The Southern New England Trunkline Trail (SNETT) resumes without markings at bend on Castle Hill Way. Surface now is packed dirt. Condition of trail worsens (sand, rocks, ballast) between Farm St and Center St in Bellingham. From Center St to Prospect St in Franklin, the dirt trail surface is groomed and in very good condition. The Prospect St bridge is now complete and the trail continues to Grove St in slightly rougher condition.
I definitely preferred this 11 mile Eastern section of the trail over the 12 mile Western section (in Part 1 of my earlier review).
Consider this a great way to travel between two lovely towns rather than a picturesque trail with stunning views all the way. However take in a great view from the end of the bay at the Lead Mines area. In summer hundreds of fishing and pleasure boats are moored between the towns of Salem and Marblehead . If ,coming from Salem , you take the right spur to Swampscott the trail ends and there isn’t much to see like there is in Marblehead or Salem. In Marblehead make sure you visit the old fort and gun battery .
Started off in Winchendon Center - plenty of parking. Trail is paved and easy. Stretches along Whitney Pond and thru some marsh land. It is really beautiful. We caught it on a overcast and pretty cool day so it was not crowded - most people were masked. Winds its way along Rt 12 an ends at North Ashburnham Rd at which point you have to take a right on the street, then a right onto Rt 12 (be careful - easy to walk tho), then take the first left onto Old Gardner Rd. Follow Old Gardner Rd a short distance (5 mins or so) to the next portion of the trail. There is also a lot here and pick up the trail. We walked only about another half hour before we had to turn and go back. This is a really nice trail. Highly recommend it. We hope the two portions somehow get connected. If not, signage would really be helpful. Enjoy.
Where this trail starts in downtown Nashua is not a great area. We biked it recently to get access to the Mine Falls Park. About half way down the trail is better but would probably have to park on a street. If you are looking for a nice bike ride I suggest the Nashua River trail. Mine Falls is nice but you are in the minority if you are biking. There are a lot of walkers.
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