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 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 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 Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
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 Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...
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 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 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 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...
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 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 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 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 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...
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...
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 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 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...
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...
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...
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 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...
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...
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
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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...
The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...
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...
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 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...
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 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 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 New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
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...
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 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...
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...
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
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...
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...
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,...
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...
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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 Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
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...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
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...
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 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 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...
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 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...
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...
The Charles River Bike Path, also referred to as the Charles River Greenway, offers a paved, 22-mile route from Boston to its western suburbs. The trail is also part of a larger, developing network...
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
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...
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 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...
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...
I started the trail with the hopes of finishing the entire thing by walking. The current construction on the Franklin portion of the trail made that very difficult to do. Furthermore, it is labeled decently enough through Franklin, portions of Bellingham and Blackstone, and then again once you reach Douglas State Forest. However, there are many miles that are unclear and involve walking through towns and near the highway. Trail maps also occasionally led us in the wrong direction. This trail was extremely difficult due primarily to the vague instruction. Some sections were very nice, but I don’t think it’s worth doing it in it’s entirety.
Your best bet is to park your vehicle at Hood Park and then you follow a street portion and cross the main road. The Depot is right in front of you, and the trail is pretty easy to follow. The ride out toward Windham is slightly uphill so the trip back seemed easier. This trail connects directly into the Windham Trail through a paved connector. I would have rated it five stars but there are quite a few street crossings and people tend to drive faster through there so be alert.
Section of the trail at Bull Hill Road is closed as well as the parking lot at this location. No information regarding why this section is closed or for how long. Would be nice if a brief sign could be posted to let users know if work is being done and how long the closure is projected to be. A lot of disappointed people driving and biking here; only to be turned around.
This is a shaded trail that parallels Highland Ave. You can begin/park at NTB/National Lumber and follow it south towards Oak Street. Along the way, occasionally there are art installations. At Oak Street, there is an adjacent bocci court and picnic tables. You can continue there for a very short bit on the trail towards the tv tower/Charles, but my recommendation would be to make a left onto Oak Street and head towards Highland Ave. Once there, if you make a right, you’ll see two DCR marble posts starting an unnamed trail that will take you along the Charles to Second Ave. if you follow Second Ave a couple of blocks, it will take you right towards Cutler Park. You can bike the length of the Futker Park loop around the lake, which often has swans. It’s a pretty extension to the Greenway Path and for almost the entire ride, you are in a path A pretty ride, I recommend it
Absolutely loved this trail ¿¿ Readily accessible from the Ayer MBTA Station. I cycled on a sunny quarantine Saturday, and I never felt unsafe or peeved by the occasional foot traffic. Shoot, one of the residences along the trail was even giving away free masks. The trail wide enough and well maintained. Overall, it was an easy, comfortable, and scenic ride from end to end. Highly recommend linking your trip to the trails of Mine Falls Park or the Nashua Heritage Rail Trail into the city.
awesome trail to work and train my dogs, only suggestion I have is trash barrels. There's only 1 in the middle. Should really have a handful or so spread out which would help keep it clean.
I used this trail to roller skate, it was pretty short but a nice straightforward skating path
Beautiful day. Yes I got off a few times to kick the poop into the woods since I don’t have a horsey bag. But there were plenty of places either rock stump or bench to mount up from. Met lots of people enjoying the day hiking or fishing. Glad i found and can’t wait to be back again
the parking lot appears to divide the trail in half, but the section directly connected to the parking lot is not a good bike trail. Most of it is covered in decomposing rail ties and it makes for an advanced but short ride before the trail ends abruptly. The way to go is on the other side of the street from the parking lot. Its a nice flat trail most of the way. The trail has a range of materials: grassy, sand, packed dirt and large crushed stone. I would recommend for a child who has a little experience on trails, not a true beginner.
Rode north from Boscawen to Highland Lake about 15 miles. Trail is in excellent shape. Very slight grade riding north such that you can hardly notice it. Ride south was faster as it was essentially downhill. Great day
This is one of my family’s favorites as it was the first rail trial we ever did. The trail is all paved, pretty much flat throughout, and easily accessed. Apparently they are planning to add an additional few miles on the northern end by 2022. The only drawbacks are that it can get crowded, it can be buggy (it is near a lot of wetland), and of you like challenging trails it isn’t the best choice for you. Overall we love it
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