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.
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...
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 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 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 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 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...
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...
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...
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 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...
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...
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...
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...
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 Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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,...
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 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 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 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 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 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 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 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 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...
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 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 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...
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...
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...
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....
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 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 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 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...
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 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 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...
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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 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 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...
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...
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach 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...
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 Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
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 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 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...
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...
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 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 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 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 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...
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 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...
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...
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...
This was our first family trail with kids that were new to bicycling. Everyone enjoyed the consistent pace of the trail. Not too crowded, but haven't tried middle of summer yet. Takes about 30 minutes to go from one end to the other and back.
The award-winning JAYCEE Arboretum and Corridor includes the welcoming 400 linear foot Esplanade filled with attractive (annuals & perennials) flowers, mini-trees, seasonal plants and 72 species of shrubs. Features include communal monuments, manicured playing fields and historic artifacts that form the portal entrance to the rugged state Senator Roch Riverwalk, a 1.3 mile wilderness trail of native vegetation, waterfowl and forest wildlife along Rhode Island's largest waterway, the Pawtuxet River and Watershed.This picturesque trail system is nestled along the all-important confluence of the north and south branches, the Pawtuxet River. Note: From time to time, a tree(s) or large branch(es) can fall prey along the Trail and should be reported to Park & Recreation authorities for disposition. The destination locations are situated along the West Bay/Washington Secondary Bikepath [quadrant of Warwick, West Warwick, Coventry & Cranston] within Riverpoint COMMUNITY Park - 110 Hay Street W. Warwick, R.I. 02893. The JAYCEE Arboretum and state Senator Roch Riverwalk, also crosses over (on-street) for a very short distance to access the newly-created (2007) West Warwick Riverwalk (a/k/a Pawtuxet River Walkway) for a trail length of about 0.5 mile(s), which runs behind the Riverpoint Village of the historic Royal Mills Apartment Complex - this will soon be an enhanced area for an Orchard and Trail system to the nearby Middle & High School Campuses parallel to factory Street upon Arctic Hill. The JAYCEES & Volunteers manage these (Arboretum-Corridor) properties that are public domain of the Town of W. Warwick. The JAYCEES coordinate a Spring Open Space celebration called, ECOLOGY DAY & PEACE PRAYER Ceremony usually on the first Saturday in May and the commemoration for the 9/11 Observance. This is addition to launching the annual Arbor & Earth Day events, a Community Program entitled, CORPORATE CARES DAYS and related projects - for schools, organizations, court-service - all open to the public!
Parked in West Warwick next to rev dept tennis courts. Hopped on trail right there. Rode in direction toward Coventry. Interesting mix of residential, industrial, mills, rural areas. Clean, level and super fun.
My husband and I rode the Upper Charles Trail from the Hopkinton start to the near end in Holliston this last Saturday in November 2020. What a pleasant surprise! We enjoyed very pretty scenery in Hopkinton, a great lunch at Oliva's Market in Milford, visited the brand new Boston Honey Company store in Holliston, and marveled at the historic Phipps Railroad Tunnel under Highland Street. The trail changes from asphalt to very rideable stonedust in Holliston. At just over 13 miles one-way, the trail is a great way to enjoy being outside and getting some great exercise to boot! I thoroughly recommend this trail to anyone who likes pretty scenery, and great stops along the way.
Rode the eastern section of this trail from the parking lot at the end of Adams St in Uxbridge to Grove St in Franklin, approximately 11 miles. For the first 3.5 miles the trail is part of the Blackstone River Greenway and is in excellent condition with smooth blacktop surface. You'll see cyclists, skateboarders, runners and walkers on this section. The improved trail ends in Blackstone at Canal St. Follow Canal St downhill, make a left onto St Paul St, then right on Main St, and left into Castle Hill Way. The Southern New England Trunkline Trail (SNETT) resumes without markings at bend on Castle Hill Way. Surface now is packed dirt. Condition of trail worsens (sand, rocks, ballast) between Farm St and Center St in Bellingham. From Center St to Prospect St in Franklin, the dirt trail surface is groomed and in very good condition. The Prospect St bridge is now complete and the trail continues to Grove St in slightly rougher condition.
I definitely preferred this 11 mile Eastern section of the trail over the 12 mile Western section (in Part 1 of my earlier review).
Phase 1- the makings of a wonderful trail! Anxiously waiting for the completion of phase 2.
I have done a couple of segments of the trail. One segment Starting in Franklin and going into Blackstone. Some parts of this trail were closed or almost impassible short of having a hardcore mountain bike not to mention that some segments are not marked at all. I have also done the segment from Rte. 98 in Douglass working east toward Blackstone there were segments that were in decent shape but there were others you can see that were rutted or still very wet given that we have been in a drought for a good chunk of the summer makes me concerned what they would be like if we had a normal amount of precipitation. Additionally, once I got near Rte. 146 the trail just seemed to disappear there were no markings to figure out where to go. Next time I will try and go from Douglass and work my way west and see how that goes. This trail has potential but needs a lot more work on it to be good.
Cycled approximately 12 miles of the trail from New Road in E Thompson, CT to RT 146 in Uxbridge, MA. The first few miles through the Douglas State Forest are in very good condition and patrolled by MA Dept of Conservation personnel. After that the trail begins to slowly deteriorate first with the surface becoming very sandy in places and then areas of ballast (large gravel) and standing water. The section from Chocolog Rd to RT 146 was challenging based on these surface conditions. You will need to look for a steep left turn down to RT 146 where singletrack runs alongside the roadway. Then watch for a steep right turn down onto Elmwood Road where the trail becomes interrupted for a short distance. To continue on the SNETT, make a left on Elmwood Rd to go under RT 146, then right onto Balm of Life Spring Road, right onto RT 146A, left onto Providence St, and finally left onto Adams St where it's possible to pickup the trail again continuing East.
There are plenty of places to sit and there are dog poop bags and a waste container at one of the seating areas. Highly recommend for walking little and older dogs.
The Air Line State Park Trail is one of my favorite bike trails in Connecticut. Rode our bikes there last week and was very disappointed with the recently resurfaced section from the Cranberry Bog in East Hampton. The gravel that was used in the resurfacing is to soft and to deep. Has only been open for a week (10/28/2020) and it is already marred by craters from horses and foot traffic. The ride is bumpy like a wash board. At one point I swerved to miss a pile of horse droppings and got to close to the edge which then collapsed under my bike causing me to fall. What was once a favorite section of the trail for us, is now a major disappointment.
We parked by the pet store mentioned in a previous review and biked to just passed the covered bridge, maybe 6 miles out? Beginning of trail is rough but that ends quickly . Nice ride in the woods. Not much to see. It was a slight incline on the way out which made the return better. I wish there some benches along the way to take a break.
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