Winchendon, MA Snowmobiling Trails and Maps

1522 Reviews

Looking for the best Snowmobiling trails around Winchendon?

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

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Activities
Length
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23 Results
Activities
Length
Surfaces
Type

Derry Rail Trail

3.6 mi
State: NH
Asphalt

Mass Central Rail Trail

59 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

Northern Rail Trail

57.8 mi
State: NH
Cinder, Crushed Stone

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

West River Trail (Windham County)

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Windham Rail Trail

4.3 mi
State: NH
Asphalt

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

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

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

Stevens Rail Trail

1.65 mi
State: NH
Crushed Stone, Gravel

Sugar River Trail

9.5 mi
State: NH
Ballast, Gravel, Sand

Concord-Lake Sunapee Rail Trail

5.65 mi
State: NH
Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Hillsborough Recreational Rail Trail

7.8 mi
State: NH
Crushed Stone, Dirt

Ware River Rail-Trail

15 mi
State: MA
Ballast, Dirt, Grass, Gravel
Accordion

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Henniker & Hopkinton Rail Trails

6.7 mi
State: NH
Dirt, Grass, Gravel, Sand
Trail Image Trail Name States Length Surface Rating
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
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
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
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
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...
MA 1.62 mi Crushed Stone
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
Overview 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. The trail is...
NH 4.3 mi Asphalt
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
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
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
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
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...
NH 6.7 mi Ballast, Gravel, Sand
Overview  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,...
NH 18.3 mi Dirt, Sand
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
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
The Stevens Rail Trail is part of the Concord-Lake Sunapee Rail Trail, which follows the historic Concord-Claremont Railroad corridor. Located about a dozen miles west of Concord, the Stevens Rail...
NH 1.65 mi Crushed Stone, Gravel
Overview  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...
NH 9.5 mi Ballast, Gravel, Sand
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
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
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
Accordion
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
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
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

Recent Trail Reviews

Salem Bike-Ped Corridor

Salem-Windham Rail Trail

July, 2024 by kroselle25

Just did this trail today from Range Road in Windham to Derry. This is a great trail and was surprisingly not that busy for July 3rd. One tiny observation, we attempted to start at the Willow St. parking area in Salem across from Dodge Grain. Things have changed there since the Rail Trail map was done, there is no parking anywhere there now. Some company has signs saying non-company business parkers will be towed. Thus we went north. However, it looks like there is an empty lot at the Main St. - Central St. intersection across from the Depot Museum in Salem. It looks to be safe to park there and the rail trail is a few steps away.

Ware River Rail-Trail

June 2024 Gravel Bike

June, 2024 by macneilkathy1994

This trail had sand, deep in areas made it not fun for gravel biking.

Blackstone River Greenway

Not a great ride

June, 2024 by pamiller919

Started from India point park and it isn’t marked where to. We lost the “route” many times because of no signage. Very bumpy, wouldn’t call it a scenic ride.

Accordion

North Central Pathway

Northern Part is the best

June, 2024 by res3737

Overall this is a great trail and one of my favorites, but I'll give you the detailed breakdown from North to South. Starting near the YMCA in Winchendon it is a beautiful paved trail with great scenery and lots of good parking here and a little further down near Glenallen Street. Just after you cross the large bridge at the beginning, there is an inconspicuous and not very inviting junction with the unpaved Ware River Rail Trail on the right that I have not ridden. I rode all the way down to North Ashburnham Road where I turned right, took a right on Route 12 for a short bit, then turned left on Old Gardner Road to get to the next section of paved trail and skipped the unpaved portion between Route 12 and Old Gardner Road. This next section is very nice as well, although I'm not a fan of the underpass at Commercial Drive because it collects water at the bottom even during the summer. I always ride the narrow dirt track over the top to avoid the water in the tunnel. There is at least one maintenance station between here and Route 140 and a few benches to stop and rest on. Once you cross Route 140, I'm not a big fan. There are no muddy spots, but that's because a lot of crushed stone has been placed in sections on the trail which makes for a very rough ride. I'm hoping this crushed stone is a prelude to placing some compacted crushed gravel for a better riding surface. We shall see. I stopped at Park Street and then rode down into Gardner from there. It is all very nice and it would be 5 stars if the southern section had a better surface.

Ware River Rail-Trail

Gates? Trucks on the Trail?

June, 2024 by res3737

I only rode the southern 3 miles of this trail between Route 122 and Route 62. The surface is not bad, no muddy spots, although there was a large pine tree down across the trail that was nearly impassable. My only criticism of this section was that there were no gates at Grange Road or Lackey Lane and I believe only on the southerly side of Covered Bridge Road which meant that I looked over my shoulder at one point to find a Toyota Tacoma bearing down on me. Why are there trucks driving on the rail trail?

Concord-Lake Sunapee Rail Trail

so much to do

June, 2024 by carmen347

I have been waiting to try this route for several years. Always hearing that it wasn’t close to being finished. I was very disappointed to see firsthand that virtually nothing has been done for those years. The first mile from Concord is covered with packed cinder, but beyond that the trail is still raw and rough with exposed rocks and roots. Not sure why this project has stalled but I will not be riding it or supporting it until domething more is done to show progress. tiding it ir supporting it until I see something

Mass Central Rail Trail

MCTR - West Boylston to Rutland

June, 2024 by closey2112

Ok, I recently purchased a ‘24 Trek Checkpoint ALR 5 axs gravel bike. This section of trail is absolutely amazing. Roughly 26.3 miles round trip from West Boylston to Rutland. Starting in West Boylston, Ma you head west. The trail is hard packed dirt. Smoother than most roads in Mass! ¿ No, seriously! Just be careful, this section up to the I-190 bridges, there’s usually a lot of traffic. Especially people with doggos. Some more cognizant than others. But once you cross under the bridges, no dogs are allowed and the traffic thins out. The best section is at the parking lot on Mill St - Holden. It’s packed gravel and as wide a road. It meanders up to the mail Trail and is packed gravel all the way until you hit construction on the trail. So much fun!!!

Northern Rail Trail

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

June, 2024 by klracicot

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

Ashburnham Rail Trail

great view: stunning panorama

June, 2024 by thiagobardini85

At the end of the trail, you'll be treated to a stunning view!

Air Line State Park Trail

Get outta here. Put an asphalt trail down or stop wasting our time.

June, 2024 by db7178

Get outta here. Put an asphalt trail down or stop wasting our time.

Rocky Hill Trail

Completely paved; easy

June, 2024 by pianoemily

This was a very short trail which was completely paved. It was nice and shaded due to the trees. It would be an easy walk with grandparents (there are benches) or young children. I recommend setting your gps to find something like 134 Sandy Hill Road in Florence. From there, you can easily find the trail beginning. To get my 10,000 steps I had to go back and forth on the trail a lot. But I still appreciated it fully paved! Seems like more of a neighborhood morning walk trail.

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.

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Accordion

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