Explore the best rated trails in Thompson, CT. 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 79 trails covering 542 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.
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
The Watertown-Cambridge Greenway runs along the former corridor of the B&M Railroad’s Watertown Branch. The trail begins in a busy shopping area on the site of a former U.S. Army arsenal. Trees...
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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...
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 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 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 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 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 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 Center Trail runs for less than a mile from Hopkinton's downtown to its high school and middle school, providing a safe route to school for thousands of students. The wooded trail, which once...
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 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...
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...
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...
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 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 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 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...
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 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 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 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...
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...
The Cochituate Rail Trail (CRT) is a developing, multi-use trail that will run from the Village of Saxonville in Framingham to Natick Center, a distance of 4 miles. Currently, its northernmost mile in...
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...
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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...
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...
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
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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 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 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 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...
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
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 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...
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 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 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...
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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 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 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 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...
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...
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 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...
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 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 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 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...
The Center Trail runs for less than a mile from Hopkinton's downtown to its high school and middle school, providing a safe route to school for thousands of students. The wooded trail, which once...
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 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 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 Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...
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...
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...
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 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...
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...
The day that I rode this trail was a beautiful Spring day and there were various other riders, walkers, runners and, in Northampton, people going for stroll. It is a well maintained trail, not too long, plenty of things to see and places to relax. Part of the trail is rural feeling, but other parts are located right near downtown. A nice mix.
I was pleasantly surprised that trail had been repaved or at least repaired. Most of the tree limbs and frost heaves are now gone. Pretty ride made better by surface upgrade - thanks
Mostly smooth and even and only a couple slopes that could send you flying. Definitely one of our favorites for inline skating.
Very smooth and safe. Great with kids and beginners. Lots of trees and not too crowded. Highly recommended.
Rode 7 miles out and then back. Beautiful area. Really good workout. Few hills. But nice quiet area midweek
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
Very pretty, well kept, no one else there in the middle of a sunny spring day!
Parked and road the trail from Fino Field in Milford. No usable facilities at the field likely due to Covid. The trail is mostly level with small grades in parts. It passes through urban, residential and forested areas. The surface is paved to the Milford line on both legs, where it then becomes hard packed process stone. Road bikes (25 mm tires) can negotiate the trail. The leg from Fino Field to Holliston is about 9.5 miles to the unimproved section, which had considerable standing water preventing further exploration. The trail passes through Holliston at the 7.5 mile mark where there are some small eateries and a town greenspace. Phipps Tunnel is noteworthy. The leg from Fino Field to Hopkington is about 4 miles to the trail terminus. The trail passes through Louisa Lake Park (picnicing and fishing). Foundations from early granite cutting sheds served by the former Hopkington RR of the late 19th century are visible on the left near the terminus of this leg.
Good bike path. Easy to access for a short ride. I saw bridges, streams, old chocolate factory, the non-stop old metro trains. Not too crowded.
Wow! I was pleasantly surprised by all the lovely artwork along this trail. The river, falls, and arch are all so pretty. Glad I went exploring ¿¿¿¿¿
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