Webster, MA Snowmobiling Trails and Maps

2075 Reviews

Looking for the best Snowmobiling trails around Webster?

Find the top rated snowmobiling trails in Webster, 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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9 Results
Activities
Length
Surfaces
Type

Mass Central Rail Trail

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

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Arkwright Riverwalk

0.8 mi
State: RI
Dirt, Woodchips

Cheshire Rail Trail (Cheshire Branch Rail Trail)

42.4 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand

Southern New England Trunkline Trail

21.8 mi
State: MA
Asphalt, Ballast, Crushed Stone

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Ware River Rail-Trail

15 mi
State: MA
Ballast, Dirt, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
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 64 miles between...
MA 72.2 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
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 Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...
RI 0.8 mi Dirt, Woodchips
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
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
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
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 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

Recent Trail Reviews

East Bay Bike Path (RI)

beautiful ride

October, 2026 by chleary11

Started at veterans memorial parking lot as per many reviewer’s suggestions. What a great ride down to Bristol! A few things to note—there are a lot of street crossings but most are not busy. There were only 2 where I had to wait and push the cross signal. There were no bathrooms on the trail but you could stop in barrington or Warren if needed. There is a bathroom at the end of the trail in Bristol. Bristol is a lovely town to stop and walk around. Colt park is a good option also, but I didn’t do the 4 mile extension. I just rode into the park and out. It was a great fall ride!

Narrow-Gauge Rail-Trail

Parking info

October, 2026 by jbhostage266

The trail map indicates there is parking at the crossing with Pine Hill Road, but it is not really designed as a parking area. There is room for one or two cars to pull off the road. There is a real parking lot with room for maybe a dozen cars at Sweetwater Avenue, the location of the Fawn Lake Conservation Area.

Air Line State Park Trail

Beware

October, 2026 by 8jp5rr55yf

So I started this trail in Portland, Connecticut, and about 3 to 4 miles into it. It stops at a marsh river area. There is no sign to tell you that it does or what detour to take. You would have to get on the main road to avoid this section. And the way people drive on that road I wouldn’t trust it. From what I heard, they were supposed to build a bridge over this section but said they were waiting for EPA to be involved which was years ago so I would highly recommend that you start in East Hampton for continued access.

Accordion

Cheshire Rail Trail (Cheshire Branch Rail Trail)

The good: it’s being paved. The bad: signage through Keene

October, 2026 by pammer1959_tl

We hoped to do the entire trail by parking in the middle just south of Keene. The signage going through town was minimal and included being on the road quite a bit. The south side noted “road closed” because it’s being paved, but the road dead ended after 2 miles.

Disappointed is an understatement.

Tri-Community Greenway

Great in section, too many road crossings

September, 2026 by robertbgates13

This trail has several wonderful, delightful, beautiful sections. But there are a few too many street crossings, and the signs could be better for those who are new.

Twin Cities Rail Trail

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

September, 2026 by cedwardpierce923

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

William C. O'Neill Bike Path

Beautiful trail

September, 2026 by susan.restivo

I love the quiet and beauty of this trail.
However, last time I was there someone
drove on the path on a scooter. I didn’t know this was allowed. It wasn’t the type to help with mobility issues.
It was loud and disturbing to the dogs walking.

Washington Secondary Bike Path

Lovely lovely trail!

August, 2026 by amygallatin

We rode from the parking lot at Quidnick St. in West Warwick to the abrupt end of the trail in Summit (Coventry), about 20 mi round trip. Pavement in very good shape. Trail is shaded for much of the way making for a pleasant ride. Lots of views of ponds, lakes, reservoirs and streams. Significant uphill climb to the end of the trail in Coventry but a screaming downhill for much of the way back. We plan to return in the fall, foliage will doubtless be stunning. Trail is paved throughout, and the western part of the trail is shared with equestrians, although sadly we did not see any.

Pine Tree Brook Path

Good for little kids Mountain Biking

August, 2026 by andrew.magruder

My 6 and 9 year old grandsons rode the 2.5 round trip with maybe 100 feet of walking their 20” mt bikes over rough spots and a couple of logs. The trail is 95% shaded. We parked on Breck Rd and crossed Thacher Rd to the trailhead. Lafayette Rd has a large circle at its end by Pope’s Pond that you clearly can park at.

Air Line State Park Trail

geminird review misleading

August, 2026 by atclaw

This rider was going Northeast from Willimantic towards Hampton NOT Southwest from Willimantic to East Hampton. Having ridden both stretches I can say his description is completely wrong about the gorgeous and open riding Southeastern route and not completely wrong but somewhat overly harsh about his route which can get iffy for stretches.

Charles River Bike Path

Skip the Western End

August, 2026 by trylondm

This trail gets better and better as you get closer to downtown Boston. It also gets more crowded. Very scenic with lots of views of the river and such, but as always in Boston, there will be detours here and there due to construction. Probably gets better the more times you ride it and get to know its quirks. Not a trail if you are looking for speedy biking due to the number of pedestrians, runners, and other folks - it is certainly well-loved by Bostonians!

Western end beyond the Galen Bridge to Waltham gets squirrelly with odd and sometimes confusing routing and signage - not recommended unless you've got all day like I did.

Nashua River Rail Trail

Still a 5 Star Trail

August, 2026 by trylondm

Yes, the comments about all the root heaves along the paved trail are true, but otherwise a very attractive ride. The TrailLink description is very accurate. Might be special in foliage season.

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Accordion

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