Find the top rated walking trails in Winchendon, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
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...
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 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 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 exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
The Bradford Rail Trail occupies a former Pan Am rail corridor, beautifying an area that once lay strewn with garbage and weeds. The city and numerous dedicated volunteers created the mile-long path...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
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...
The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
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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...
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 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 health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
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...
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 Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
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 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 40 miles from Boston to Northampton...
Mile 0.0 - DPW Garage Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
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...
This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
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 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 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...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
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Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
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 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 Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 4.5-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
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...
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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 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,...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
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...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
The year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
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 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 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 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,...
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...
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 Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
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 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 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...
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 Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
The year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
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 health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
This trail is perfect for riding your bike through the woods, fun and scenic!
Short trail but gorgeous trail along the river. Mallard ducks, beautiful fall colors and peaceful at dawn on October 11.
This was my first time on this trail, despite driving by it more times than I can count. What a wonderful ride. Mostly flat, but some low grade rises. Can’t wait to come back again- maybe tomorrow!
Started in Nashua 1st time doing this trail and i have to say we loved it. Loved the little town of Pepperell while biking thru and continued to Groton.
Love the scenery and nature. We will be going back again.
I love it here . We started in Windham and went all the way to Tuscan kitchen restaurant . It was a nice ride .
Excellent trail have been using the Londonderry rail trail which is great to but this trail has more scenery to view as you walk. Walked 8.7 miles of the trial this morning was great plan on coming back the only thing I would add is to update the trail map the trail now continues after range road. I recommend this trail it’s well maintained to
This is a beautiful bike path, easy to moderately easy (has a couple hills) that runs along the Blackstone River. So many places to stop and see the water, especially at the falls. As other reviewers mentioned, GPS goes a little crazy here and took us out of our way-- it does not recognize Rivers Edge Recreation area (parking lot) as a destination. I suggest you put in 195 Davison Ave, Woonsocket, to get to the northern trail head parking lot (called River's Edge.) We started there and rode down 6.1 miles to Ashton Village mill and (across the bridge) museum. A Fix-it station, with tools and an air pump is located there. The trail continues down to Slater Mill in Pawtucket (another 6+ miles) but we were looking for a shorter ride today and turned around here to head back. FYI the first waterfall is in Lincoln, about 1.5 miles from River's Edge parking lot- it is beautiful! The second one is about another mile from there (both are manmade.) Those were the only two on this 6 mile stretch. The park ranger at Ashton suggested next time we park in Ashton and complete the ride down to Slater Mill, where there is a natural waterfall and the ride is very pretty.
Great trail real nice walk lots to see parking closed on the southern end
A great stretch of nature nestled away in the suburbs. A peaceful walk on a beautiful day.
Just did this yesterday (9/14/20) starting from Woods Crossing to the northern terminus at the American Legion then back, going past my parking location to the MA line. From the border up to I'd say the Rt. 202 section, it was quiet, saw 2 people but mainly around the Rt. 202 starting point. Comparing to sections north of it, the southern area is more wooded and a narrower trail but easily ridden with a hybrid bike. Anything with skinnier tires would probably have a harder time for the whole length of it. The northern section was quite busy, many walking, enjoying the weather. It is a little more scenic and the trail is wider. Trail is mainly gravel or hard packed dirt throughout though a little loose sand in the southern section in a few spots but not much. At some trail entrances, there is a sign which gives you some pointers as to what you will see along that stretch, gives you something to to try and see instead of just staring down the path.
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