Find the top rated bike trails in Webster, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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 Locks. Due...
The South Bay Harbor Trail connects several Boston neighborhoods—Lower Roxbury, the South End, Chinatown, and Fort Point Channel—to the Boston Harbor. The trail spans nearly 4 miles from Ruggles...
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 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...
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 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 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 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...
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 pleasantly tree-lined Warren Bike Path, built along the former Warren-Fall River Railroad, runs just under a mile from Long Road west to the Kickemuit River. The trail ends in an 18-acre park...
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 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...
More and more, airport lands near previously under-used rail corridors are being transformed from largely neglected vacant lands into urban greenways. These new vibrant spaces are used not only by...
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...
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 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...
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...
The World War II Veterans Memorial Trail opened in Mansfield in 2004 after several decades of advocacy by local rail-trail supporters. The trail rests on an abandoned corridor once served by the Old...
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...
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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,...
The South Bay Harbor Trail connects several Boston neighborhoods—Lower Roxbury, the South End, Chinatown, and Fort Point Channel—to the Boston Harbor. The trail spans nearly 4 miles from Ruggles...
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...
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 40 miles from Boston to Northampton...
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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...
In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...
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...
With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...
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...
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...
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,...
Riverpoint Park sits nestled into a bend of the Pawtuxet River in West Warwick, Rhode Island. The park accommodates the 400-ft arboretum which leads to 1.3-mile riverside path known as the Senator...
The Tri-Community Greenway follows the route of the Boston and Lowell Railroad and its Stoneham Branch, originally built to serve Stoneham’s shoe factories and provide passenger service. The Greenway...
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,...
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,...
Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...
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 developing Upper Charles Trail will one day total 24 miles, linking the communities of Milford, Ashland, Sherborn, Holliston, Framingham, and Hopkinton along a former railroad bed. As of 2018,...
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...
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
More and more, airport lands near previously under-used rail corridors are being transformed from largely neglected vacant lands into urban greenways. These new vibrant spaces are used not only by...
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....
Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...
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...
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 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 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...
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...
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...
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 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...
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 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 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 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 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 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...
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 health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
Excellent mid-morning Summer ride - Tuesday, so not a lot of traffic on the trail. A two mile road section is required to connect the two sections of the trail. This is not a problem as long as you are careful on the road. The trail is fully paved except for the two mile section on Track Road adjacent to the Assabet River National Wildlife Refuge. I would not recommend a road bike on this section. It is dirt and gravel with a few bumps, but not a problem for trail bikes. The scenery in this area is impressive as it is on the Acton end as well. Total distance approximately 12.5 mi. Recommended.
I started at the southern portion of the trail. I rode a gravel road / light touring bike (Specialized Sequoia) and it was fine but in hindsight I would have done a bit better with the FatBoy. There was a fair amount of sand in the first portion of the trail. I encountered some decent sized muddy sections but nothing crazy. The variety of scenery is great and the trail is very quiet. I encountered about 3 other bikes and a couple of people walking. I wouldn't do this trail if there's been significant rain in the past few days because of the pooling that I saw in some of the sections flanked by rock walls. And I rode in July and was flanked by large flies seemingly at all times. But given the challenge and scenery it's worth it!
I love this trail and ride it often. Once you ride or walk it you will keep coming back for more. I live in neighboring Billerica and ride the 3 miles from my home to the head of the trail which is hidden in the parking lot on the side of Cross Point (900 Chelmsford St. Lowell Ma.). There is tons of parking here so you will never have to worry about getting there early to get a space. There is a lot of foot traffic in the beginning of the trail until you get to Chelmsford, Rt 110, but once you cross the street and enter the bike path I have never experienced a lot of traffic (bike or foot) from this point to the end of the trail in Acton. A lot of the trail is tree lined which provides partial shade on a hot, sunny day. There are two beaches along the trail, Heart Pond in Chelmsford, and Nara Park in Acton. Further along the trail, near the end is a bike shop, Pedal Power Bike and Ski, which is nice to have and they offer facilities for your relief. Speaking of which there are facilities along the trail at Heart Pond, Nara Park, the parking lot at Brook St. and the bike shop. If you like to explore there is plenty to see with farms and historic homes along the Chelmsford section of the Trail. The trail ends at a sports complex with a loop to turn around. At the northern end of the sports complex is a small meadow which is nice to rest and enjoy lunch. As for food there are plenty of place to eat along the trail.
I rode this trail on 7/12/19 from Moosup, CT east into Sterling, CT. The first 5 1/2 miles are unimproved rail trail, good for MT bikes or aggressive hybrid riders. At the route 14A crossing I found some improvements underway, 1.5 miles of bull dozer work to a bridge under construction just past Carbuncle Pond WMA. The surface was soft and broken and very hard to ride. This leads me to believe that Road Island has a project underway to extend the Trestle Trail from Log Bridge Road (the current end) westerly to just west of the CT line at Route 14A. I will explore the area in the late fall to see how work has progressed. There is a second bridge in the Village of Green, RI that needs work, but I did not get that far.
If the entire trail were like the section in Holliston, I would have given this a 5 star. The Holliston section is the high point of the trail. It's well maintained and does not have too many busy street crossings and has a nice canopy to block the sun. The paved section in Milford has a busy cross by 495 and is a bit weird as you head into downtown. At one point a narrow sidewalk has a painted divider and you also need to head behind a shopping center to catch the trail as it has a small break. The Milford section has its nice spots though, by the lake and the park, but the 495 section isn't a highlight nor the downtown break. Also the map shows the trail ending in Sherborn at a street. If you have a road bike or a hybrid you'll probably end at the Sherborn line, which is in the woods. The last .3 miles of the trail is single track better for mountain bikes that will take you to the road.
Tuesday July 09, 2019, 5:30 pm.
Weather 88' F, low humidity, very light clouds.
Great weather for riding this great trail. Massachusetts really sets the bar for bike trails. This one has a line down the middle to help the careless riders better their performance. There are benches near view spots with poems and examples of flora and fauna carved into boulders. There are granite mile markers on both poles and pavement stones at the side of the trail. The pavement was very smooth and there are only some slight inclines. Tunnels and bridges, a variety of scenery, this is both a community trail and a destination trail. I drove 2.5 hours for this one and the much shorter Canalside trail a half hour away in Turner Falls, doing both on the same day with a mid-trip visit to the Bridge of Flowers in Shelburne Falls. All 3 places worth the trip, but now I have to complete the other sections of the Mass Central Greenway. Good job Massachusetts!
Got there early Sunday morning with just a couple of walkers and a jogger or two. Riding my road bike was easy but the gravel section from Holliston soon threw sand into the drivetrain. After 4.25 miles it changed to paved and I washed out the sand. The rest of the ride was easy and most pleasant. The map shows an extension North of Holliston but this did not look inviting so did not go.
I parked at 15 Spring Lake Road in Sterling. A very brief portion is paved, up to the bike overpass, then its mogul after mogul. Great for mountain biking, not so much for hybrid or road biking. Sand, gravel, muddy bits...unkept. Beautiful area, share the trail with dirt bikes and at atvs either direction.
Have been riding this trail before the 7 arch bridge was repaired. Even better now, the ride is longer and very shady. One of my favorite trails in Mass.
Very nice and shady, pleasant ride.
We did the trail from Hudson to Marlborough and were going to drive to the trail head in Maynard to check out the other section of this trail. However we found out the directions are incorrect. You need to go EAST on 117 not west. I hope this will be corrected. We did enjoy the trail from Hudson to Marlborough but that is mostly up hill and not gradual in some areas. I suggest going from Hudson so you get the down hill on the way back.
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