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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

Grand Trunk Trail

6.9 mi

State: MA

Crushed Stone, Dirt, Gravel

Harrisville and Hancock Rail Trails

6.1 mi

State: NH

Dirt

Head's Pond Trail

1.75 mi

State: NH

Gravel

Mass Central Rail Trail

56.36 mi

State: MA

Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Mine Falls Park Trails

9.7 mi

State: NH

Asphalt, Crushed Stone, Dirt, Grass

Monadnock Recreational Rail Trail

7.5 mi

State: NH

Asphalt, Gravel

Northern Rail Trail

59 mi

State: NH

Cinder, Crushed Stone

Redstone Rail Trail

1.4 mi

State: MA

Asphalt

West River Trail (Windham County)

16.1 mi

State: VT

Asphalt, Dirt, Gravel, Sand

Ashburnham Rail Trail

1.3 mi

State: MA

Dirt

Ashuelot Recreational Rail Trail

21.4 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)

42.4 mi

State: NH

Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Fort Hill Recreational Rail Trail

7 mi

State: NH

Ballast, Cinder, Dirt, Gravel, Sand

Mason Railroad Trail

6.7 mi

State: NH

Ballast, Gravel, Sand

Narrow-Gauge Rail-Trail

3 mi

State: MA

Asphalt, Crushed Stone, Dirt

New Boston Rail Trail

3.9 mi

State: NH

Dirt

Accordion

Old Railroad Trail

2.7 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 mi

State: NH

Crushed Stone, Dirt, Grass, Gravel, Sand

Southern New England Trunkline Trail

21.8 mi

State: MA

Asphalt, Ballast, Crushed Stone

Squannacook River Rail Trail

3.7 mi

State: MA

Crushed Stone

Sugar River Trail

9.5 mi

State: NH

Ballast, Gravel, Sand

Brookline Rail Trail

4.5 mi

State: NH

Crushed Stone, Gravel

Concord-Lake Sunapee Rail Trail

5.65 mi

State: NH

Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi

State: NH

Ballast, Cinder, Dirt, Grass, 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

Barker Road Trail

0.9 mi

State: MA

Dirt, Grass

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

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 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 is nearly...	CT	60.3 mi	Ballast, Crushed Stone, Dirt, Gravel	150 reviews
	Derry Rail Trail 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 southern...	NH	3.6 mi	Asphalt	26 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	16 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	6.9 mi	Crushed Stone, Dirt, Gravel	10 reviews
	Harrisville and Hancock Rail Trails Harrisville and Hancock Rail Trails run for 6 miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris Center...	NH	6.1 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. The Mass Central Rail Trail runs for 36.36 miles from...	MA	56.36 mi	Asphalt, Cinder, Crushed Stone, Dirt, Gravel	93 reviews
	Mine Falls Park Trails 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	21 reviews
	Northern Rail Trail Spanning 59 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 than a 2-hour drive...	NH	59 mi	Cinder, Crushed Stone	72 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
	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	3 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	21.4 mi	Asphalt, Ballast, Cinder, Crushed Stone, Dirt	42 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	2 reviews
	Cheshire Rail Trail (Cheshire Branch Rail Trail) The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of uses,...	NH	42.4 mi	Asphalt, Ballast, Cinder, Dirt, Gravel, Sand	46 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	13 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
	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	22 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	8 reviews

Accordion

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	3 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	16 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 runs from Manchester, the state’s...	NH	28 mi	Crushed Stone, Dirt, Grass, Gravel, Sand	63 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	21.8 mi	Asphalt, Ballast, Crushed Stone	67 reviews
Squannacook River Rail Trail The Squannacook River Rail Trail is 3.7 miles long, from Depot St in the center of Townsend, MA, to the Bertozzi Wildlife Management Area in Groton, MA. The trail occupies the Greenville Branch of the...	MA	3.7 mi	Crushed Stone	2 reviews
Sugar River Trail The Sugar River Trail runs for 9.5 miles between Claremont and Newport along the old Sugar River Railroad corridor. The 9.5-mile trail crosses its namesake river seven times—twice on covered...	NH	9.5 mi	Ballast, Gravel, Sand	31 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	1 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	2 reviews
Granite Town Rail-Trail 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 found along...	NH	3 mi	Ballast, Cinder, Dirt, Grass, Gravel, Sand	4 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	14 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
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
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

Sugar River Trail

Beautiful & surprisingly peaceful

August, 2025 by ktrenaud

Visited this trail 8/2/25. It rained the previous day which helped with the dust and packing the loose sections. NOT for skinny tires!! I was fine with my gravel bike but had it been dryer it would have been tougher but doable. There were a few ATV's & dirt bikes but they were VERY respectful and always gave us plenty of room on the trail. The river is gorgeous with plenty of access points to get your feet wet. If you're starting out on the Claremont side I'd recommend parking at the Home Depot just down the road from the trailhead. It's slightly uphill all the way to Newport which makes for a very easy ride coming back. Spoke to a local police officer parked at the trailhead and he said they're going to start patrolling the trail very soon to nab speeding ATV's which I consider a bonus.

Blackstone River Greenway

one of my favorite trails

July, 2025 by wq6pp9sd4p

I live in Massachusetts about 25 minutes from this trail, my absolute favorite trail is the East Bay bike path, but that is about an hour drive for me, so this is one I frequent more often. I like the length of this ride, and that it is scenic, and more interesting than some of the rail trails that can be kind of boring. I think it is an easy ride, with just a few spots I need to lower my gears. I pack a lunch, snacks, and can be out for a few hours. There is ample parking, 195 Davison Ave Woonsocket is the address I use for WAZE. I have never gone as far as Providence, so I can only review Woonsocket - Lincoln.

Narrow-Gauge Rail-Trail

Not sure about this one

July, 2025 by robertrollins28079

Wife & I completed the Minuteman Trail & I wanted to do either the Narrow Gauge Trail or the Reformatory Trail. Wife headed for the Bedford library while I set off for the Narrow Gauge Trail. Trail was in good shape & I was prepared for the surface conditions associated with crushed stone. What caused me confusion was a lack of trail markings. I rode for about 20 minutes or so & eventually came to a gate, which was in the open position. I wasn't sure if this was the end of the trail (and still unsure at this point). I looked for signs, etc & saw none. The trail appeared to continue, but it's condition was much less pristine i.e. large ruts and valleys. I rode for what seemed like another mile until I came to a paved road & straight ahead was a paved road with a "Private Road" sign. I exited here & took surface streets back into Bedford. I am giving the trail a 2 star rating; better signage would increase my evaluation.

Accordion

Minuteman Commuter Bikeway

Pleasant summer bike ride

July, 2025 by mollyrollins008

In Boston area last week for a conference and decided to try out the Minuteman Trail. Spouse and I have been enjoying bike/rail trails over the past few years and usually one of the first things we check out when traveling to a new area. Trail was in great shape & was as good as expected. Being summer, it was pretty hot weather but the trail provided ample shade for us to stay cool. Particularly appreciated the history of the trail, and it's relevance to Paul Revere's late night ride. This was our first time in the Greater Boston area, as we're from North Carolina. All in all, a good ride and fun experience.

Cochituate Rail Trail

A delightful paved trail in excellent condition. Relatively flat with some pretty views of the lake. There is a side spur to Speen Street that connects to the Natick Mall. Great for a quick and easy ride.

July, 2025 by dan339g

A delightful paved trail in excellent condition. Relatively flat with some pretty views of the lake. There is a side spur to Speen Street that connects to the Natick Mall. Great for a quick and easy ride.

Air Line State Park Trail

My Ride July 21, 2025

July, 2025 by 9q8skpdwwc

I took a ride on a gravel bike from Putnam to Willimantic and back yesterday. I crossed the bridge in Putnam from Kennedy Drive (a nice paved path there along the north shore of the river!) to pick up the Air Line, which my map app shows as starting there. Though there were some short bits of various trails there, none of them went anywhere. I ended up back on roads and made my way to Town Farm road where the Air Line commenced, with signage. However, the next several miles were very rough, and I would not recommend riding there except with a balloon tire mountain bike with front and back suspension. But from the Pomfret Station on to Willimantic, it was either beautiful, or at least fine, except for some road crossing s with very steep and rocky ramps on both sides. For most riders, those ramps have to be negotiated off the bike. But overall, I had a great experience!

Upper Charles Trail

Great ride

July, 2025 by hz45mrq5bv

Did the whole thing west to east and back in one ride. Enjoyed the history for the trail that was posted along the trail. Give you a chance to stop, slow down and just enjoy the ride. Half of the trail is stone dust but still good. No big ruts and water channels (even with all the rain we had recently). Plenty of parking along the way is you want to jump into a section of the trail. There are even repair station on the trail if you have a bike problem. Greatly appreciate the convenience of it. Enjoy the ride!

Air Line State Park Trail

Airline Trail Pomfret Ct section

July, 2025 by artzub

July 19 2025
Just rode from Pomfret west to the Rt6 overpass. Most of the trail is good riding except for some rocky sections, but the overgrowth is starting to close off the trail in sections. It is down to just one lane. It would be nice if the state could mow the weeds.

Grand Trunk Trail

Pleasant Ride

July, 2025 by macmeier22

We are stayin at Pine Lake RV resort and wanted to do a paved bike ride. The gravel road reviews made me uncertain. But it was great. Some small inclines but nice ride to the Westville Dam. Very nice destination for a bike ride. Took road back on other side of dam. Much more mountain bike ride but still easy enough. So glad the parking lot was marked well. We almost drove 30 miles for another ride.

Medfield Rail Trail

Easy walk but the trail is not paved on the Medfield side; perfect if you want to minimize the impact on your knees

July, 2025 by rstphard

Easy walk but the trail is not paved on the Medfield side; perfect if you want to minimize the impact on your knees

Ashuelot Recreational Rail Trail

I love this trail!

July, 2025 by 6z87r5x5ct

I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!

Nashua River Rail Trail

July, 2025 by rthomps1963

Rode the trail on Saturday 7/5/25. Liked that it was well shaded, rode by water, not many cross overs where you had to stop for cars and not crowded. I liked the trees on both sides. My only complaint would be you really need to make sure you have front end suspension when riding as there are alot of tree roots growing up under the asphalt- bumpy- outside of that it was a great ride!

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