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.
_144627_st.jpg)
_147891_st.jpg)
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....
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 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...
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 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 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...
_75158_sc.jpg)
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
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...
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...
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...
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 Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being...
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
_0_sc.jpg)
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 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...
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...
_148569_sc.jpg)
Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
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 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...
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 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 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 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 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 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...
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
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...
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 Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
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...
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...
_147891_sc.jpg)
The Blackstone River Greenway (previously known as the Blackstone River Bikeway) represents a big undertaking in this tiny state: The 11.8-mile trail running between Woonsocket and the outskirts of...
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...
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
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...
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...
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...
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...
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 Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...
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 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 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 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...
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,...
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...
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....
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 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 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 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...
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...
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...
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...
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...
August 2017
It was a great ride, next to a river, shady, smooth, and there is a parallel Farmington Canal trail that meets this one at the southern end. The north end is near a conjesting roadway and was supposed to continue on a non-paved section, but I could not find it. Go check it out.
Dateline June 21, 2018, 4:00 pm, sunny 81F.
I wish there were more time that day to continue longer, onto the connecting trails. After driving 2.5 hours to another trail only to find the parking lot closed I had little time to enjoy this one, but it is nice.
ADVICE: If you are driving farther than 30 minutes (like I often do for Trailink trails), (1) always review the trail listing on this site for updated information, (2) bring more than one parking lot address, (3) and a second choice trail with 2 parking lot addresses. And/or get the mobile app.
For a returnee to the bike riding crowd, I found this trail to be a hidden gem. Does not have the scenic views of the East Bay Bike Path but what it does have more than compensates.
So we started in Cranston. It was a of an bit urban feeling but that did not last long. It quickly assumed the characteristics of a rural bike path. Layered canopy overhead with woods, swamp lands and the occasional home or housing development.
Challenge? Oh yeah. The almost slight constant uphill kept me pedaling. Could we coast some ways? Yes, but not for long.
So after a hour and some 45 minutes we achieved the terminus in Coventry.
We sat having snacks and talking with other bikers. I made mention of the complaints on this forum about the 'conditions' of the path. (I always mention TrailLink to others when biking!)
I found the path to be in excellent shape. Were there some slightly overgrown areas, yes but it did not block progress or impede a view at all.
The return trip was AWESOME!!! There is about 3 to 4 miles of a constant downhill grade. We hit a high speed of 21MPH without even trying. For this first 4 miles, our average speed was 17.6MPH. For the next seven we averaged just over 13MPH.
Even with killer cramps that stopped me short at the 34 mile point (lost 15 minutes) and 37 mile point (lost 10 minutes), it was a great ride an worth the 38+ mile effort.
The Portland section does not connect up to the East Hampton section and the rest of the Air Line Trail. I found out today when I thought I was going to ride from Portland to the Air Line Trail North. I only rode 2 miles and the trail abruptly ended.
The Air LIne Trail South is now open through part of Portland. Parking is off of Middle Haddam Rd. in Portland.
Slight grade makes walking or riding great for a novice. Intermittent sun at bridges and clearings. Ice cream stand available in Blackstone with playground. Love this!
Yes, the trail is short, but it's very near my home and so great for daily exercise. I'm just beginning to ride my recumbent trike in a serious way, and so I do 3-4 laps every day. It's quiet, peaceful, and very well-maintained.
Today was the fourth time I walked this trail from holliston walked 2.5 miles and back.
Very easy walking the packed stone and dust pavement. I walk the Henry Hudson trail in NJ nearly every day 5 miles and both these trails provide some of the most interesting sites.
When visiting my family here this provides me a great walk. Wonderful
We have ridden this trail before, and really enjoyed it, especially the part near the ponds below Oxford Airport. We expected it to be somewhat rough, and we are always willing to walk through particularly wet/mucky areas and to put up with rough stretches. However, the trail has really gotten much worse. After about 2-2.5 miles in, it became extremely sandy/silty, and we could only ride on the narrow edges. Then at about 4 miles in, there was a stream flowing through the whole trail, with nothing but mud and muck; no way to ride through, as it continued as far as we could see, so we had to turn around. End of ride for the day...
I love walking this trail. I have yet to make it to the end with the kids as they get tired we have gone most of the way. I walk there a few times a week with them. They love seeing the turtles in the water. Only thing I dislike is those who dont clean up after their dogs. I have stepped in dog doo on the trail, and alot of those who do clean up throw the colored baggies in the bushes so you always see colored bags oi n the ground and un the tree.if your not going to take the bag with you then leave the pool it will eventually go away your bag on the other hand will go nowhere :(
Rode the trail this morning (a Wednesday). Very light and friendly walkers with few bikers. Trail is in very good condition -- both the gravel portion in Holliston and the paved portion in Milford. Plenty of benches to pull over and rest if you want...but the trail is about as flat as you get so the riding is easy. Will return many times.
Get Your 2018 RTC TrailNation Jersey!
Download the TrailLink mobile app and take TrailLink with you!
Donate and Get a FREE 2018 RTC Guidebook!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_148569_st.jpg)
_75158_st.jpg)
_0_st.jpg)
_139112_st.jpg)
