Explore the best rated trails in Windham, CT. Whether you're looking for an easy walking trail or a bike trail like the Upper Charles Trail and Windsor River Trail . With more than 60 trails covering 445 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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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 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...
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...
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 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...
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...
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...
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...
Bookended by beaches and offering gorgeous vistas of Niantic Bay, the Niantic Bay Boardwalk is a must-do excursion in the small Connecticut village of Niantic, part of the larger Town of East Lyme....
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 Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
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 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 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 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 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 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...
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 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 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 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 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 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 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 Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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 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 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...
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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...
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 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 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 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...
Quonset Point Bike Path is a fantastic two and a half mile trail. The Quonset Point Bike Path is a part of the beautiful town of North Kingstown.The Quonset Point Bike Path is paved and off road and...
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...
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 Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
Quonset Point Bike Path is a fantastic two and a half mile trail. The Quonset Point Bike Path is a part of the beautiful town of North Kingstown.The Quonset Point Bike Path is paved and off road and...
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 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 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 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...
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 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 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...
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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...
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
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...
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 Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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 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 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 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...
The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
Excellent ride. All asphalt and very well maintained. We went on a Friday morning and still found it to be crowded. We did the whole trail from E. Providence to Bristol round trip in 3 hours. This trail is a definite do again.
Nearly perfectly flat - good compact ground - three nice bridges - very little other traffic.
We had two kids, 8 and 11, with medium bike skills - easy going here so was all fun and no hassle. We started in the middle (parking area) and went to each end and back. Total 6 miles, took 1 hr due to stops to view wildlife.
Only drawback: we wanted more miles !!
Rode from Southington to New Haven and back. Beautiful trail. A must for anyone biking in CT.
Beginning at the eastern point in Northampton, this is not well signposted. It connects with the western end of the Norwottuck trail heading west by turning right (turning left goes to the Manhan trail) at the T junction once you have gone through a tunnel having crossed the Connecticut River and crossed a couple of roads. It takes you to Florence / Leeds including the Look Memorial Park in Leeds. Heading west, having turned right onto this trail from the Norwottuck trail it goes behind a commercial building and seems to stop. At this point you come out between these buildings facing a road. Cross this road at the traffic lights and go through the Stop and Shop parking lot to the left of the supermarket building. There is an official gap in the fence where you can join the rail trail. It is not marked. Follow the trail to the right. It is a little bumpy with roots to start with but is a nice scenic paved trail.
Generally this trail is in good condition, paved all the way, few lumps and bumps with tree roots etc. The bit that isn't marked well is where it joins the Norwottuck trail in Northampton. If you start on the Norwottuck trail heading west this trail begins by turning left once you have gone through a tunnel having crossed the Connecticut River and crossed a couple of roads. The other direction - that also is not marked - takes you to the Northampton bike path to Florence / Leeds - more about that in the respective review for that bike path. The Manhan trail crosses over Main Street right by the railroad station and takes you through Northampton - a good interesting ride on to Easthampton and Southampton where it dead ends.
There is currently detours at two places In Barrington where wooden bridges are closed. This is a major nuisance. Does anyone know if there are plans to rebuild these bridges and if so when the trail will be back to normal. I love this trail but would have second thoughts about riding there again till this is corrected and right now I see no indication there is preparation to fix this.
Started at the western trailhead on Kettletown Road. Nothing but a single track -- including a climb down to Jeremy Swamp Road to cross and then a climb up the other side. Clearly, decades ago there was a rail bridge here, but it's gone. For a while, the trail is fine, but then another problem on this leg is that the trail becomes virtual impassible for bicycles -- you are trying to ride up a creek bed full of grapefruit sized rocks.
East of Strongtown/CT 188, there is a mix of beautiful gravel surface through the woods with some low spots/mud (we've had some rain). The route is wooded and quiet -- really nice ride. You will likely encounter horses (I passed a single rider and a pair on this ride). Etiquette is to be very careful and slow -- give them a shout as to which side they'd prefer you pass on. Also a lot of wetland. If you're moving fast on a bike, it's OK, but walking you're going to be dealing with A LOT of mosquitoes.
Summary -- with some investment this could be one of the prettiest rides in CT, but there are some real rough/muddy spots.
I can see where this could be a beautiful autumn ride. Will give it a few more tries this season.
The foot bridge and immediate surrounding view very pretty is the highlight. The walk is flat and hard to find. You go under a road with concrete supports sprayed with a lot of graffiti and then leave a crushed gravel path for a concrete walkway over a marsh. The marsh is a habitat for egrets. The path was more for bicyclists, who were impatient about walkers on trail. dismounting for walkers. We skipped the concrete path due to heat and people on bikes
This section has been open for a year or two now (June 2020) and is excellent condition all along following the power lines. Approximately 4 miles long end to end with nice smooth black top ideal for cycling, now also attracting walkers, skaters etc. There are footpaths into the adjacent woods.
There is a car park at the Wayland end easily accessible from the intersection of rte 126 and 27. At the eastern end the last access point is at Church Street, Weston. Further east it just dead ends at a decrepit bridge.
The actual bike path, itself, is just a bit over 11 miles. The southern end starts at Blackstone Valley Prep high school in Cumberland. The northern end starts in Woonsocket near Mendon rd. It does connect to the East Bay, but it is about 7 miles of street in between Cumberland and Providence.
Smooth ride with few interruptions. Fairly busy but it was a sunny Sunday and Father's Day. The trail maintenance was immaculate minus a minor detour in Barrington; they had it temporarily blockaded for tree trimming work.
Polite riders and walkers along the way. Loved the trail-friendly stops and shops from beginning to end. Watchemoket Cove isthmus is truly picturesque.
Must stop at Sunset Cafe in Bristol! Cheerful mom-and-pop serving up hearty and flavorful sandwiches for a fair price.
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