Find the top rated trails in Windham, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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...
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 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 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 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 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...
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 paved Charter Oak Greenway rolls more than 13 miles through the tree-covered hills and eastern suburbs of Hartford before crossing the Connecticut River and ending in the capital’s downtown. At...
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 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 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...
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...
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...
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...
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 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...
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...
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 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...
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...
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...
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 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 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...
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...
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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...
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 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 Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
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 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...
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 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...
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 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 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 Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
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 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 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...
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 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 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...
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...
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...
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 Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
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,...
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 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 paved Charter Oak Greenway rolls more than 13 miles through the tree-covered hills and eastern suburbs of Hartford before crossing the Connecticut River and ending in the capital’s downtown. At...
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 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 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 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...
We started in Providence at India Point Park. It was a beautiful blue bird day in the high 70's with little to no wind. A perfect day for a bike ride. However, after riding the entire length of the trail from Providence to Bristol and back, we feel this is another Hall of Fame Trail that is so over hyped it is almost criminal. First, there are no facilities anywhere on the trail. Be prepared to buy lunch somewhere if you need to go to the bathroom. The trail surface is paved and in excellent condition with lane markers dividing the trail. It is probably the best trail surface we've ever ridden on. It is very flat, but it is also very narrow. You will have to watch out for walkers and runners, ALL of whom ignore the trail signs and walk against the flow of bike traffic. Be prepared to do a lot of weaving in and out of traffic. When it comes to scenery, the bridge that you cross when leaving India Point Park from the Providence trail head is beautiful. Then there is one small section of trail about a half a mile long where the trees form a very pretty tunnel you ride through. As you get into Bristol, you get some views of the bay, (which are for the most part obscured by chain link fencing). However, for the most of the trails length, there is nothing to see except the small trees and scrub brush that lines both sides of the trail. There really isn't anything to see. For as much as this trail is hyped as a Hall of Fame Trail, we expected much more, and to be honest, were thoroughly disappointed, and left wishing we had just ridden one of our local trails instead.
I found this trail to be very easy and smooth. No bumps along the way. It’s got a few disconnects but nothing major. Hilly at times which gives you a work out. It would be awesome if it went all the way to the ocean! We parked at the train station which was crowded on a Sunday late morning.
Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.
I just road the Airline Trail across the Willimantic River and then toward the newer ending at Mackie's Ag. Store near the Columbia town line. It was in fine shape. However, what I was looking for is evidence that the work on the Willimantic River bridge was started. I found nothing underway. I road to the easterly end of the Hop River Trail hoping that it was starting at that end. No such luck. Does anyone out there have any information on when this section will be started?
This is a really nice trail, most of it is under a canopy of trees, nice scenic spots on the river if you want to stop for lunch. I took my hybrid the full 40 miles out and back. Except for maybe a half mile of stones and gravel in Bolton Notch where a mountain bike would be better, the rest was nice hard pack dirt and pulverized stone. I saw thin tire street bikes on this trail as well. There are very long stretches on this trail where you don't cross any roads, and except for maybe one exception, most of the crossings have little traffic and are side roads. I also like the width of the trail. Two thirds of the trail is very wide. After Andover it gets a bit more narrow but there were also fewer people on the trail towards Willimantic. The only down side is that the trail terminus in Willimantic is pretty anticlimactic. You come to a road that that's it. No parking lot or grassy area, just a road and you know its over unless you want to continue on-road biking to Willimantic.
As of September 8th 2018 there is only one thing holding back the expansion of the Charter Oak Trail from Porter Street to the Hop River Trail in Bolton, the bridge over Camp Meeting Road. It should be the completion of just a few details that will allow this section to be open to the public: accepting the last bridges and some land scaping work. Once the bureaucracy is done, riders will be able to connect from East Hartford to Bolton and beyond. That's about 15 miles of the Charter Oak Trail and 20 miles of the Hop River Trail that will be connected, finally. Of note, there are two more bridges in Windham and Columbia at the eastern end of the Hop River Trail that are going to bid this fall. Once done, it will open a trail from the Hartford area to Pomfret CT. Be patient. What's another year or so to get all these trails linked.
Nice easy ride. After Washington Secondary and East Bay, this is a nice relaxing ride.
I am lucky emough to live 1/2 mi from the Farmington Valley Trail and use it quite frequently along with a few of my friends.
I used to ride my horse along this route before it was scheduled for paving for a rail trail. Back then very FEW people used it. Mostly young motorcross kids and horseback riders.
Since it has been paved - horses are now NOT ALLOWED!! (Too bad for us); but as I have moved away from horse riding to personal trail use I am SO HAPPY that I have this wonderful gift in my back yard. There are many many miles and it spans on into southern massachusetts as well.
The trail itself is wonderful; paved, stripe’d and mowed in my area. I have ridden into Mass and south to Simsbury. Before my section was paved I had to load my bike and drive to Simsbury and unload, reload etc. Now, I just hope onto bike (or walk) and go for as long or far as I choose. The scenery is mostly rural, treed and very few homes are seen unless you are crossing streets. I know there are black bears near our home (area) but have not SEEN one ON the trail (daytime use).
It is SUCH a marvelous thing - and I see dozens and dozens of folks biking, walking, & rollerblading. Its a joy to be out in nature!!
Well-maintained, great bike ride. Lots of really cool stops along the way. Beautiful views on the trail north of Hartford.
The length of the trail is terrific, and the Coventry section (~9 miles) is wonderful, with a bridal path, lakes, pine forests, wooden planked bridges and very well maintained.
I started in West Warwick, ~ half way through the end-to-end, and first 2 miles were a bit sketchy for a single woman riding alone, but I got over my discomfort quickly. It was very easy to find the Horgan Elementary School and the trail right behind the school - plenty of parking.
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