Webster, MA Cross Country Skiing Trails and Maps

2016 Reviews

Looking for the best Cross Country Skiing trails around Webster?

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

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Activities
Length
Surfaces
Type
48 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Assabet River Rail Trail

10.4 mi
State: MA
Asphalt

Blackstone River Greenway

31.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Border to Boston Trail

44.1 mi
State: MA
Asphalt, Boardwalk, Concrete, Crushed Stone, Dirt

Bruce Freeman Rail Trail

15.7 mi
State: MA
Asphalt

Charles River Bike Path

23.4 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

East Bay Bike Path (RI)

14.3 mi
State: RI
Asphalt, Boardwalk

Farmington Canal Heritage Trail

49.1 mi
State: CT
Asphalt

Grand Trunk Trail

6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Manhan Rail Trail

9.5 mi
State: MA
Asphalt

Mass Central Rail Trail

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

Medfield Rail Trail

1.3 mi
State: MA
Asphalt, Crushed Stone

Minuteman Commuter Bikeway

10.1 mi
State: MA
Asphalt

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

Nashua River Rail Trail

12.4 mi
State: MA, NH
Asphalt

Neponset River Greenway

8.2 mi
State: MA
Asphalt

Phenix-Harris Riverwalk

0.3 mi
State: RI
Dirt

Quinebaug Valley Rail Trail

5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass
Accordion

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Ten Mile River Greenway

3 mi
State: RI
Asphalt

Upper Charles Trail

13.9 mi
State: MA
Asphalt, Crushed Stone

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

William C. O'Neill Bike Path

7.2 mi
State: RI
Asphalt

Arkwright Riverwalk

0.8 mi
State: RI
Dirt, Woodchips

Burrillville Bike Path

1.2 mi
State: RI
Asphalt

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Charter Oak Greenway

16.5 mi
State: CT
Asphalt

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

Narrow-Gauge Rail-Trail

3 mi
State: MA
Asphalt, Crushed Stone, Dirt

North Central Pathway

11.2 mi
State: MA
Asphalt

Northern Strand Community Trail

9.9 mi
State: MA
Asphalt

Putnam River Trail

2 mi
State: CT
Asphalt

Reformatory Branch Trail

3.9 mi
State: MA
Dirt

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

Tri-Community Greenway

10.6 mi
State: MA
Asphalt

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Moosup Valley State Park Trail

5.8 mi
State: CT
Crushed Stone, Grass, Gravel

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
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
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 10.4-mile trail. It offers a forested escape for...
MA 10.4 mi Asphalt
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Border to Boston Trail is a developing trail network that will stretch 70 miles between the New Hampshire border and Boston—providing a continuous route for a variety of non-motorized uses...
MA 44.1 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Dirt
A developing rail trail, the route winds for nearly 16 miles through Chelmsford, Westford, Carlisle, Acton, and Concord. The rail trail is paved and is typically about 10 feet wide.  About the...
MA 15.7 mi Asphalt
The Charles River Bike Path, also referred to as the Charles River Greenway, offers a paved, 23-mile route from Boston to its western suburbs. About the Route A large section of the trail,...
MA 23.4 mi Asphalt
The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. About the Route The rail-trail runs between the Westfield...
MA 3.1 mi Asphalt
Offering spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path is a 14.3-mile trail that connects historic New England waterfronts along several river mouths of the...
RI 14.3 mi Asphalt, Boardwalk
Closure notice: During the week of July 7th, the FCHT will be closed due to repaving from Copperhill Road to the Suffield line and then from RT. 189 to Floydville Rd. First a canal, then a...
CT 49.1 mi Asphalt
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
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail trail dive through steep rock cuts...
CT 20 mi Crushed Stone
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
MA 9.5 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. The Mass Central Rail Trail runs for 36.36 miles from...
MA 56.36 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Built along the former Bay Colony Railroad line, the Medfield Rail Trail stretches between Ice House Road in the Town of Medfield to the town's border with Dover. Running primarily through woods, the...
MA 1.3 mi Asphalt, Crushed Stone
For many commuters, the Minuteman Commuter Bikeway provides freedom from congested traffic in the northwest Boston suburbs. For others, the 10.1-mile paved trail between Cambridge and Bedford serves...
MA 10.1 mi Asphalt
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 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...
MA, NH 12.4 mi Asphalt
The Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...
MA 8.2 mi Asphalt
The Phenix-Harris Riverwalk, a short trail built on a former rail bed purchased from Penn Central Railroad, connects West Warwick and Coventry, two towns on the outskirts of Providence. The dirt...
RI 0.3 mi Dirt
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
MA 5.7 mi Ballast, Cinder, Dirt, Grass
Accordion
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 Southwick Rail Trail extends for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line. About the Route Along the way, the Southwick Rail Trail travels...
MA 6.5 mi Asphalt
Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...
RI 3 mi Asphalt
Shaped like a checkmark, the Upper Charles Trail links Milford, Holliston and Sherborn—towns in Massachusetts’s bucolic MetroWest suburbs. Ornamented by an eight-arch stone bridge and a historic...
MA 13.9 mi Asphalt, Crushed Stone
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. About the Route The rail-trail, Rhode Island’s...
RI 19.2 mi Asphalt
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
MA 0.7 mi Crushed Stone
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
RI 7.2 mi Asphalt
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
Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once...
RI 1.2 mi Asphalt
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The Charter Oak Greenway offers more than 16 miles of paved pathways through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
CT 16.5 mi Asphalt
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
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
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...
MA 11.2 mi Asphalt
The Northern Strand Community Trail runs almost 10 miles through the cities of Everett, Malden, Revere, and the town of Saugus and provides a variety of experiences.  About the Route Access the...
MA 9.9 mi Asphalt
The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
CT 2 mi Asphalt
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
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 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
The Tri-Community Greenway is a 10.6-mile multiuse trail that connects Stoneham, Woburn and Winchester. Part of the route runs along a former railroad corridor. About the Route At its southern...
MA 10.6 mi Asphalt
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but trail...
CT 4.2 mi Crushed Stone, Dirt
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
CT 5.4 mi Asphalt
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 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...
MA 0.21 mi Asphalt
This 5.8-mile trail runs between Moosup and the Rhode Island/Connecticut border. Wide and flat, this rail-trail is suitable for riders of all levels. The surface is a mix of paved asphalt and granular...
CT 5.8 mi Crushed Stone, Grass, Gravel
The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
CT 0.75 mi Asphalt

Recent Trail Reviews

Air Line State Park Trail

Willimantic to East Hampton - Just AWFUL!

August, 2025 by geminird

The claim of this being a 61 mile trail is very deceptive. Almost 40 miles of this trail is nearly unrideable except for mountain bikes (and even that would be unpleasant). We are experience riders and were on hybrid bikes with wide tires and front suspension. And while our plan was to cycle 40 miles from Willimantic to E. Hampton, we only did the first 10 mile section from Willimantic to James L. Goodwin State Forest.

The trail started out as just OK, but deteriorated in less than 2 miles. After crossing S. Brook Rd, the trail the trail was extremely gnarly and super overgrown. When we reached Goodwin State Forest, we were so happy to bail out and call it quits! Luckily, we had a SAG vehicle with us so we weren't forced to cycle back over the same awful trail.

Be warned, the entire trail we rode from Willimantic to Goodwin Forest was large, loose gravel, and the scenery is incredibly boring. There are places where the trail is extremely rough. At S. Brook Rd. the trail becomes unrideable, expect by maybe some die-hard mountain bikers. We used our SAG van to pop into other points along the trail from Goodwin to E. Hampton the trail only seemed to get even worse.

Honestly, just a really unpleasant ride.

Charles River Bike Path

Charles River Bike Path. August 18, 2025

August, 2025 by amy2paul

My husband I decided to ride this trail on our visit to Boston. We parked at 31 McKenn Street in Waltham and rode in towards Boston, then crossed the river to ride back on the other side. First, I'll start with the positives. It has areas with nice shade and the views along the river are neat. Now for the negatives. The trail boasts it is all asphalt. It is not. There were many spots with packed dirt surface. Even though I don't like riding on anything but asphalt or concrete, this at least was pretty smooth and level. NOT compared to the badly maintained asphalt and concrete. The vegetation needed to be trimmed, the path was NOT marked at all (luckily my husband had a map on his phone), many sections were very narrow, not wide enough to have two bikes pass and the asphalt had many cracks that I had to be careful to watch for. Sorry but whoever has the contract to maintain this trail is falling down on the job. Boston is such a neat city so I won't let this trail color our experience as totally bad, but you couldn't pay me to ride this trail again.

World War II Veterans Memorial Trail/Norton Rail-Trail

Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.

August, 2025 by gconner02019

Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.

Accordion

Air Line State Park Trail

A Fabulous, Friendly, and Easy Trail !!!

August, 2025 by pedego2015

We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose

North Central Pathway

nice ride

August, 2025 by dmzast

rode trail july 28, 25 from Winchendon - slight uphill, going south to Gardner. Adding mile markers would be nice ! and directions at N.Ashburnham Rd to Old Gardner Rd. Newly paved from entrance off
Old Gardner Rd to Gardner town line. Path to avoid watery underpass was paved on one side of street.

East Bay Bike Path (RI)

a great goes through beautiful surroundings

August, 2025 by jhoff1

It is such a lovely trail. The view is gorgeous, either from the ocean or from the land. It goes through a few towns, all lovely and friendly. There are shops along the trail for you to stop by for ice cream, coffee or lemonade. There are a few road crossing, but the cars are very friendly and stop to let cyclists cross. The destination Bristol is just beautiful! Some areas are in the open, so the wind can be your friend or not …..

Nashua River Rail Trail

Great trail, good for all seasons.

August, 2025 by jhoff1

It is a great trail for all seasons. Parking available in Ayer, Groton, Pepperell and Nashua

Bruce Freeman Rail Trail

great trail, best between heart pond and NARA park

August, 2025 by jhoff1

It is a very well maintained trail. My favorite part is between the heart pond and the NARA park. More road crossing beyond that region in both directions

East Bay Bike Path (RI)

nice paved path

August, 2025 by rdpd2025

It’s a nice paved path, shaded half way through. Good for families with kids. Parking is free but though to find, suggests keep following the path till you find parking. There are several options along the way from the eastern end of the trail. Few food and restroom options, within coffee or mall shops. Public restrooms are very limited at least when starting from east end. We went only half way and back, with kids. Looking forward to finish the second half soon.

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.

Malden River Greenway

pretty view

July, 2025 by 98td7xp28h

It’s my go to trail because it’s so close to my house ! you can walk down close to the river it’s cute . i always get to see ducks in the pond

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.

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Accordion

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