Explore the best rated trails in Webster, MA. Whether you're looking for an easy walking trail or a bike trail like the Fresh Pond Bikeway and Upper Charles Trail. With more than 91 trails covering 630 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
The Fresh Pond Bikeway runs through Fresh Pond Reservation, a park in Cambridge, Massachusetts. The bikeway winds around the east edge of the Fresh Pond Reservoir. Part of the trail is on a road...
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...
The Malden River Greenway is part of the Mystic Greenways trail system, which also includes the Wellington Greenway and the Mystic River Greenway. When completed, it will run along the Malden River...
Connecting the cities of Watertown and Cambridge, the 2-mile 12ft-wide paved Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The southern end of this multi-use trail...
The Cochituate Rail Trail (CRT) is a multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. The segment in Framingham was completed and...
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...
The Twin Cities Rail Trail is a 4.7-mile that will ultimately connect downtown Fitchburg and downtown Leominster, providing both recreation and an alternative commuting route for residents. As of June...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
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...
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...
The Pine Tree Brook Trail travels alongside the brook in Milton, Massachusetts. The path travels through woods and residential neighborhoods for a distance of about 1.8 miles, and it connects to the...
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...
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The Southwest Corridor Park (Pierre Lallement Bike Path) knits together neighborhoods in southern Boston from the Back Bay to Jamaica Plain. Popular as a route for commuters as well as casual walkers,...
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...
The West Warwick Riverwalk is located in a park just behind West Warwick High School and John F. Deering Middle School. The paved trail goes for about a mile north following the Pawtuxet River. A...
The URI (University of Rhode Island) Bike Path provides a safe conduit for students, faculty and staff to commute to and from school via the William C. O'Neill Bike Path. The asphalt, two-lane path...
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...
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...
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...
The Upper Falls Greenway is a short rail-trail that cuts through the charming village of Newton Upper Falls in Newton, Massachusetts. The trail occupies the same former rail corridor as the developing...
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...
Many commuters choose the Minuteman Commuter Bikeway for freedom from congested traffic in the northwest Boston suburbs. For others, the 10.1-mile paved trail between Cambridge and Bedford serves as a...
The Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
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...
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...
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...
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...
The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
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...
The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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 50 miles from Boston to Northampton...
The Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
The Northern Strand Community Trail is part of the visionary and almost-complete Bike to the Sea plan to link Boston and the Mystic River to the seashore in Lynn, north of Boston. It currently runs...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
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...
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...
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 8.6-mile paved trail, though long-range plans...
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...
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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 you’ll...
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...
The Mystic River Greenway is part of the Mystic Greenways trail system, which also includes the Wellington Greenway and the Malden River Greenway. When completed, the trail will connect the...
The Wellington Greenway is a section of the Malden River Greenway in Medford, Massachusetts. Eventually, the Wellington Greenway will be connected to the other sections of the Malden River Greenway in...
The Quarries Foot Path offers a wooded 1-mile hiking route in western Quincy, about 10 miles south of Boston. Begin your adventure on the south side of Ricciuti Drive, which borders Quincy Quarries...
The Fred Lippitt Woonasquatucket River Greenway provides a valuable crosstown connector of nearly 7 miles from downtown Providence to the city’s western neighborhoods and the nearby town of Johnston....
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...
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,...
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
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 50 miles from Boston to Northampton...
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...
Connecting the cities of Watertown and Cambridge, the 2-mile 12ft-wide paved Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The southern end of this multi-use trail...
The Charles River Bike Path, also referred to as the Charles River Greenway, offers a paved, 22-mile route from Boston to its western suburbs. The trail is also part of a larger, developing network...
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...
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
I highly recommend this trail for beginner bike riders. It’s approximately 8 miles from Natick (Washington Ave) to Framingham. The terrain is mostly flat with very few gentle inclines. There is one hill but can be avoided by going across route 30…I do not recommend this! The trail is well maintained. Nice foliage and of course the Cochituate River. You will meet friendly adults, kids and dogs along the way. I promise you won’t be disappointed. Th
Great trail,we loved it, but needs to be cleaned in september ....
This trail is not to be missed. I rode approximately 21 miles from Cumberland to Woonsocket. There is a parking lot on John Street at the site of the old Lonsdale drive-in. The trail is breathtakingly beautiful and well maintained. You are lulled into a calm feeling listening to the river. The surroundings rustic. It’s a mix of old and new from the railroad tracks to industrial buildings to modern buildings. There are minimal hills/inclines. My only negative is that the signage needs improvement. industribuilding
Great 14 mile round trip bike ride from the train station. Beautiful scenery with bridges, water and lines with trees. Train station has a nice bathroom and cool inside - historic, has a water fountain and a bathroom.
Fantastic trail. I started at in Marlboro (at Lincoln St). Serene and peaceful. Great combination of shaded and sunny areas. The surface is flat and mostly downhill for the majority of the route. However…on the way back was when it turned into a workout. Gentle and moderate inclines. If you aren’t used to this, there are plenty of benches to take a rest along the way.
I went to ride this trail for the first time from New York State. It was fair at best. It’s probably fine for folks who live there and know where to go when the actual trail ends. Being it was my first ride there, I could have used a couple of signs to direct me in the right direction. I got to Collinsville and had no idea where I was going. Finally gave up and went back. It could use a little maintenance along the River where the tree roots break through the pavement. Not impressed.
We spent two days on the trail doing an out and back loop each day as we only had one car. I used a mountain bike; my wife had a Townie Go, with electric assist (both 2" wide tires). The first day we started at East Hampton, road 18 miles north and turned around. Great ride. The surface was cinders, maintained and smooth. There are no bathroom or water facilities. You really feel out in the woods and away from civilization - we saw no sandwich store or stops of any kind. But, a Super day in any case. Don't miss the covered bridge which is at the end of a down hill road adjacent to the trail (about 1.5 miles)
We stayed at the Daniel Rust B&B (cottage) which is well worth it. Very nice garden like yard. Room was clean, bright and good sized. Owners were very friendly. Unbelievable breakfast - better than home. Bikes were very safe kept outside our cottage.
Good food nearby - we went to the Hill top restaurant which was reasonable and offered good choices. It faces west for a very nice sunset.
Next day we started in Lebanon and parked near Kingsley road. Note the route from here has been changed. As you near the Willimantic river you cross a pedestrian bridge. At the end of the bridge the trail splits with the Hop river trail going left and the airline going right. No more dramatic drop off at the river or the remains of a bridge you can't cross.
Taking the Airline trail follow the river till you come to a rail yard. Go straight ahead riding on public streets behind old buildings. Follow Bike Trail signs and painted bike signs on the road (River road I think) till you get to the FROG bridge on Jackson St. Make a left, following the bike trail signs into a parking lot (referred to in the itinerary for day 2 parking) on the right side just past the bridge. Ride along the path away from the Frog bridge, the airline trail picks up at the far end of this parking area (it may be called a Green way on signs - not Airline. For a few miles the path is paved asphalt but then changes back to cinder.
We rode the next part of this trail for about 10 miles till we got to a road crossing with Parker Road. From here the trail became very narrow - single track and was very rough. Basically a combination of dirt with natural stones. It seemed unimproved - no sign of cinders or any serious trail work. We rode this for a mile or so then decided to turn around. Perhaps this was only a short section of nasty trail because the itinerary makes no mention of it.
This was a fun trail with the exception of the last section. The surrounding country side is beautiful and easy to navigate with your car. Food is plentiful and there are lots of antique stores and other neat things to see. This could be a really good ride during the fall foliage season. I'll be back.
Fantastic! Parked my car at Cross Point lot. The trail is a bit choppy at the beginning; however, it gets better quickly and is easy to follow. The trail is shaded an well maintained. Very serene and not to be missed!
An excellent trail. Not really the best choice for nature-bathing, but surely the most pleasant way to ride between Fitchburg and Leominster. Smooth, wide, and flat. Lots of street crossings but they’re all pretty well done.
From EBBP over mostly dedicated path or protected bike lanes:
Over Washington Bridge thru India Pt Park;
Under I-195 along S. Water St. crossing Wickendon St. onto bike path along Providence River;
Cross Michael S. Van Leesten Memorial (pedestrian) Bridge over river then head west uphill along Ship, Chestnut then Clifford Streets;
Clifford St over I-95 bridge, dogleg right/left onto Friendship St downhill left onto Broad;
Along Broad then right onto Peace St (next to St. Joseph's Med Ctr);
Peace turns into Waverly. Waverly left onto Cranston St.;
Cranston St. (unprotected) under Rte10 then left onto Depot St.;
Arrived!
Brutal…started at the trailhead in Douglas State Forest en route to the finish in Franklin…combo of compacted gravel, sand, asphalt, and river stone….
This trail is listed at 22 miles but my gps had it at 23.9 due to not taking into account the unconnected parts where you need to navigate main roads and streets(Millville 0.6 miles not on the map and Blackstone 1.0 miles not on the map). Start to finish back to start a 48 mile day.
Absolutely NO gain on this trail…you will be peddling for 99% of the ride due to little elevation changes…many erupted stones, fallen trees, and ‘porpoising’ swells along the track…oh and mud…
And there are only 3 locations to egress off if you have any problems along the way(Millville on rte 146a / downtown Blackstone / Bellingham near the Ri border near downtown Woonsocket)…other than that your in no man’s land…
Good point is that the paved greenway in Uxbridge is new and in excellent condition with great views and bridge trusses to cross…however there are trail sections with plenty of gnarly - one bike width only - narrow points to navigate(ie. Bellingham)
My son and I completed this end to end recently. You need plenty of patience as the directions and published maps are a joke…there are 2 areas that are “under construction” and say do not enter - feel free to ignore those…as this part of the trail is rideable but just awaiting a coat of asphalt on top of compacts clay/sand…to bypass would add another 5 miles to the voyage.
The best riders would be hard pressed to finish this coast to coast under 4hrs…you can make up time on the greenway but you will be constantly peddling on this beast of a trail if you wish to complete it…looking for a challenge and punishment this delivers…hydrate and stretch!
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