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Winchendon, MA Mountain Biking Trails and Maps

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Looking for the best Mountain Biking trails around Winchendon?

Find the top rated mountain biking trails in Winchendon, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.

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Name
Length
Most Popular

Air Line State Park Trail

60.3 mi

State: CT

Ballast, Crushed Stone, Dirt, Gravel

Derry Rail Trail

3.6 mi

State: NH

Asphalt

Goffstown Rail Trail

5.5 mi

State: NH

Dirt, Grass, Gravel, Sand

Harrisville Rail Trail

1.6 mi

State: NH

Dirt

Head's Pond Trail

1.75 mi

State: NH

Gravel

Mass Central Rail Trail

59 mi

State: MA

Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Mine Falls Park

9.7 mi

State: NH

Asphalt, Crushed Stone, Dirt, Grass

Monadnock Recreational Rail Trail

7.5 mi

State: NH

Asphalt, Gravel

Northern Rail Trail

57.8 mi

State: NH

Cinder, Crushed Stone

Old Railroad Trail

2.7 mi

State: NH

Dirt

Redstone Rail Trail

1.4 mi

State: MA

Asphalt

West River Trail (Windham County)

16.1 mi

State: VT

Asphalt, Dirt, Gravel, Sand

Ashuelot Recreational Rail Trail

21.5 mi

State: NH

Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Bobby Woodman Rail Trail

1.7 mi

State: NH

Dirt, Gravel

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi

State: NH

Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Concord-Lake Sunapee Rail Trail

5.65 mi

State: NH

Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Fort Hill Recreational Rail Trail

7 mi

State: NH

Ballast, Cinder, Dirt, Gravel, Sand

Grand Trunk Trail

6.8 mi

State: MA

Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi

State: NH

Ballast, Cinder, Dirt, Grass, Gravel, Sand

Mason Railroad Trail

6.7 mi

State: NH

Ballast, Gravel, Sand

Accordion

Narrow-Gauge Rail-Trail

3 mi

State: MA

Asphalt, Crushed Stone, Dirt

New Boston Rail Trail

3.9 mi

State: NH

Dirt

Potanipo Rail Trail (NH)

2.7 mi

State: NH

Crushed Stone, Gravel

Reformatory Branch Trail

3.9 mi

State: MA

Dirt

Rockingham Recreational Rail Trail (Fremont Branch)

18.3 mi

State: NH

Dirt, Sand

Rockingham Recreational Rail Trail (Portsmouth Branch)

28.1 mi

State: NH

Crushed Stone, Dirt, Grass, Gravel, Sand

Southern New England Trunkline Trail

22 mi

State: MA

Asphalt, Ballast, Crushed Stone

Sugar River Trail

9.5 mi

State: NH

Ballast, Gravel, Sand

Hillsborough Recreational Rail Trail

7.8 mi

State: NH

Crushed Stone, Dirt

Hoot, Toot and Whistle Trail & Riverwalk

2.3 mi

State: VT

Dirt

Ware River Rail-Trail

15 mi

State: MA

Ballast, Dirt, Grass, Gravel

Ashburnham Rail Trail

1.3 mi

State: MA

Dirt

Barker Road Trail

0.9 mi

State: MA

Dirt, Grass

Brookline Rail Trail

4.5 mi

State: NH

Crushed Stone, Gravel

Catamount Trail - Sections 1 and 2

18.1 mi

State: VT

Dirt

East Branch Trail (VT)

0.5 mi

State: VT

Gravel

Henniker & Hopkinton Rail Trails

6.7 mi

State: NH

Dirt, Grass, Gravel, Sand

Potanipo Rail Trail

3.4 mi

State: MA, NH

Crushed Stone, Gravel

Potanipo Rail Trail (MA)

1.7 mi

State: MA

Crushed Stone, Gravel

Squannacook River Rail Trail

1.8 mi

State: MA

Crushed Stone

Warner Rail Trail and Bagley Rail Trail

1 mi

State: NH

Crushed Stone, Gravel

Trail Image	Trail Name	States	Length	Surface	Rating
	Air Line State Park Trail Overview The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway...	CT	60.3 mi	Ballast, Crushed Stone, Dirt, Gravel	145 reviews
	Derry Rail Trail Overview This exquisitely maintained 3.6-mile paved rail-trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. About the Route Starting at the...	NH	3.6 mi	Asphalt	24 reviews
	Goffstown Rail Trail 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...	NH	5.5 mi	Dirt, Grass, Gravel, Sand	15 reviews
	Harrisville Rail Trail 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...	NH	1.6 mi	Dirt	1 reviews
	Head's Pond Trail 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...	NH	1.75 mi	Gravel	5 reviews
	Mass Central Rail Trail 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 60 miles from Boston to Northampton...	MA	59 mi	Asphalt, Cinder, Crushed Stone, Dirt, Gravel	90 reviews
	Mine Falls Park 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...	NH	9.7 mi	Asphalt, Crushed Stone, Dirt, Grass	12 reviews
	Monadnock Recreational Rail 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...	NH	7.5 mi	Asphalt, Gravel	20 reviews
	Northern Rail Trail Overview Spanning nearly 58 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less...	NH	57.8 mi	Cinder, Crushed Stone	69 reviews
	Old Railroad Trail 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...	NH	2.7 mi	Dirt	1 reviews
	Redstone Rail Trail 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...	MA	1.4 mi	Asphalt	7 reviews
	West River Trail (Windham County) 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...	VT	16.1 mi	Asphalt, Dirt, Gravel, Sand	13 reviews
	Ashuelot Recreational Rail Trail Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...	NH	21.5 mi	Asphalt, Ballast, Cinder, Crushed Stone, Dirt	41 reviews
	Bobby Woodman Rail Trail The Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...	NH	1.7 mi	Dirt, Gravel	1 reviews
	Cheshire Rail Trail (Cheshire Branch Rail Trail) Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...	NH	32.9 mi	Asphalt, Ballast, Cinder, Dirt, Gravel, Sand	45 reviews
	Concord-Lake Sunapee Rail Trail Following the historic Concord-Claremont Railroad corridor, the Concord–Lake Sunapee Rail Trail will eventually connect communities from Concord to the southern point of Lake Sunapee via a multiuse...	NH	5.65 mi	Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel	1 reviews
	Fort Hill Recreational Rail Trail 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...	NH	7 mi	Ballast, Cinder, Dirt, Gravel, Sand	12 reviews
	Grand Trunk Trail 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...	MA	6.8 mi	Crushed Stone, Dirt, Gravel	9 reviews
	Granite Town Rail-Trail Overview The Granite Town Rail-Trail runs for 3 miles in Milford, New Hampshire. Portions of the route are unpaved and surfaced with sand, gravel, and/or dirt, while short concrete sections can be...	NH	3 mi	Ballast, Cinder, Dirt, Grass, Gravel, Sand	3 reviews
	Mason Railroad Trail 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...	NH	6.7 mi	Ballast, Gravel, Sand	19 reviews

Accordion

Narrow-Gauge Rail-Trail 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...	MA	3 mi	Asphalt, Crushed Stone, Dirt	21 reviews
New Boston Rail Trail 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,...	NH	3.9 mi	Dirt	7 reviews
Potanipo Rail Trail (NH) Following the Nissitissit River through the woods, the Potanipo Rail Trail offers beautiful river views and launch sites for canoes or kayaks. Composed of two segments, the multi-use path is roughly...	NH	2.7 mi	Crushed Stone, Gravel	1 reviews
Reformatory Branch Trail 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...	MA	3.9 mi	Dirt	18 reviews
Rockingham Recreational Rail Trail (Fremont Branch) 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...	NH	18.3 mi	Dirt, Sand	14 reviews
Rockingham Recreational Rail Trail (Portsmouth Branch) 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...	NH	28.1 mi	Crushed Stone, Dirt, Grass, Gravel, Sand	58 reviews
Southern New England Trunkline Trail 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...	MA	22 mi	Asphalt, Ballast, Crushed Stone	64 reviews
Sugar River Trail Visitors to the Sugar River Trail (also known as the Sugar River Recreational Rail Trail) can be forgiven if they lose track of which side of the river they’re traveling. The 9.5-mile trail crosses...	NH	9.5 mi	Ballast, Gravel, Sand	28 reviews
Hillsborough Recreational 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...	NH	7.8 mi	Crushed Stone, Dirt	11 reviews
Hoot, Toot and Whistle Trail & Riverwalk 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...	VT	2.3 mi	Dirt	4 reviews
Ware River Rail-Trail The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way. Following along the Burnshirt...	MA	15 mi	Ballast, Dirt, Grass, Gravel	12 reviews
Ashburnham Rail Trail 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...	MA	1.3 mi	Dirt	1 reviews
Barker Road Trail Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...	MA	0.9 mi	Dirt, Grass	0 reviews
Brookline Rail Trail The Brookline Rail Trail winds through the New Hampshire woods and passes by several small bodies of water, including the Potanipo Pond. The rail-trail has two segments, known as the Brookline Rail...	NH	4.5 mi	Crushed Stone, Gravel	0 reviews
Catamount Trail - Sections 1 and 2 The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...	VT	18.1 mi	Dirt	0 reviews
East Branch Trail (VT) The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...	VT	0.5 mi	Gravel	1 reviews
Henniker & Hopkinton Rail Trails The Henniker Rail Trail is an unpaved single-track path that follows a former rail corridor for 2.3 miles. The rail-trail picks up east of the former passenger station. Situated south of the Town of...	NH	6.7 mi	Dirt, Grass, Gravel, Sand	0 reviews
Potanipo Rail Trail The Potanipo Rail Trail is composed of three segments across New Hampshire and Massachusetts. Running through the woods along a former a rail corridor, the trail parallels the Nissitissit River for a...	MA, NH	3.4 mi	Crushed Stone, Gravel	0 reviews
Potanipo Rail Trail (MA) Paralleling the Nissitissit River as it runs through the woods, the Potanipo Rail Trail heads south towards Pepperell from the New Hampshire-Massachusetts state border. The Massachusetts section of...	MA	1.7 mi	Crushed Stone, Gravel	0 reviews
Squannacook River Rail Trail The Squannacook River Rail Trail is presently 1.8 miles long, from Depot St. in the center of Townsend, MA, to the Harbor Church parking lot in Townsend Harbor. The trail occupies the Greenville...	MA	1.8 mi	Crushed Stone	0 reviews
Warner Rail Trail and Bagley Rail Trail The Warner Rail Trail and the Bagley Field Rail Trail are part of the Concord-Lake Sunapee Rail Trail, an eventual 34-mile rail-trail connecting Lake Sunapee and Concord, New Hampshire's state...	NH	1 mi	Crushed Stone, Gravel	0 reviews

Recent Trail Reviews

Mason Railroad Trail

Wonderful, well maintained trail

May, 2024 by twelch11

A lot of work has been done to this trail in the spring of 2024. Although most trails in this area took a hit due to bad weather, people have stepped up and cleaned and improved this trail considerably. Several washouts were repaired and the Mason section of the trail was graded and ruts were filled in. This is an easy trail with lots of things to see and explore. An old quarry with a great history is just off the main trail and worth exploring. The trail is well marked and easily assessable. There is ample parking at several spots along the trail.

Head's Pond Trail

Great parking lot off rt3 in Hooksett. Packed gravel trail for the most part. Absolutely beautiful wetlands and woods. A wildlife paradise.

May, 2024 by chefmark.mrg

Great parking lot off rt3 in Hooksett. Packed gravel trail for the most part. Absolutely beautiful wetlands and woods. A wildlife paradise.

Blackstone River Greenway

Woonsocket to Valley Falls area

May, 2024 by andrix

A very nice paved 10 mile (one way) trip with plenty of birds & turtles. Park at Rivers Edge Parking to get started. Along the way the posted history is interesting, there are 3 large dams to check out and on this beautiful sunny day lots of wildlife. Once you get to Valley Falls area the trail ends and on-street begins. We continued on for maybe 2 miles but the signs were not consistent and the traffic was troublesome enough we turned back. Our rating only applies to the paved 10 mile section.

Accordion

South Manchester Rail Trail

Smooth paved rail trail, from start to finish. Park at Walmart, for ez access. Saw some turtles, squirrels, and big fat bunny ¿. Friendly people walking, bike riding, and an elderly lady on a mobility scooter. FUN!!!

May, 2024 by chefmark.mrg

Smooth paved rail trail, from start to finish. Park at Walmart, for ez access. Saw some turtles, squirrels, and big fat bunny ¿. Friendly people walking, bike riding, and an elderly lady on a mobility scooter. FUN!!!

Canalside Rail Trail

Alongside the canal, an easy ride

May, 2024 by davidcareyvermont

I took my bike over the Canalside Rail Trail while my wife shopped at BJ's, and it was a perfect opportunity to check out this lovely short trail. For the 22nd April 2024, the weather was really good yet there were only few other walkers on the trail at the same time. I was able to park at the southern, McClelland Farm Road, end of the trail where there are only half a dozen spots, but there are many more parking spaces at the northern end.
The trail was in more than satisfactory condition and the signage was also nicely in place, not that it was really needed. I didn't have time to stop in at the Discovery Centre Museum but I did return to BJ's in plenty of time to pay for my wife's shopping that day. I had a lovely time so much so that I plan to take my wife on the same trail whenever I get my old tandem up and running.

Spicket River Greenway

urban trail, easy to follow

April, 2024 by reg13

Trail connects to the Methuen Rail Trail via a confusing ramp (at the north end of the park). It’s narrow and turns a lot so you won’t go fast, but it’s paved and was easy to follow. MBTA commuter rail near the east end. I liked it because you see a bit of the city as get through safely.

Assabet River Rail Trail

good trail except for the gap and the muddy section

April, 2024 by reg13

The part between Sudbury Rd and the wildlife refuge entrance at White Pond Rd is dirt and can be impassable mud. The rest of the gap is pretty sketchy, two-lane road with no shoulder. The wildlife refuge is great too.

Mystic River Greenway

next to the highway

April, 2024 by reg13

Useful as a connector and seems to be popular for recreation but you’re next to a highway the whole time

Watertown Community Bike Path

extension of the Watertown Cambridge Greenway

April, 2024 by reg13

It extended the path a little bit to the west. This is a two-way separated lane next to Arsenal St, that is fine until it ends just when it’s needed most, leaving you to fend for yourself in a super dangerous intersection.

Watertown Linear Park Trail

pointless trail

April, 2024 by reg13

A mostly pointless path that doesn’t connect to anything because the rest of the rail route is gone. The city could make a connection through the parking lots at the east end so you can get to the Watertown Cambridge Greenway, which starts about 1/4 mile east of the harrowing intersection at Watertown Square, and the river paths.

Watertown-Cambridge Greenway

Important connector and not too crowded

April, 2024 by reg13

Now extends from Fresh Pond in Cambridge/Alewife to near Watertown Sq, and connects to the Charles river paths (at a few points) and many shopping needs. Pavement is good except a spot near School St.

Bruce Freeman Rail Trail

Great for training half and full marathon

April, 2024 by trishle9

There’s tons of long stretches of trail that doesn’t require you to wait for pedestrians signals. And not many major intersections stops. Trail is mostly flat with a few rolling inclines and declines.

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