Explore the best rated trails in Windham, CT, whether you're looking for an easy walking trail or a bike trail like the East Bay Bike Path (RI) and Warren Bike Path . With more than 60 trails covering 495 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.
This is a good trail, but if you start in Milford and do the entire checkmark there are a lot of street crossings. The pretty parts of the trail are nice and shady and wooded, but there is a fair amount of commercial areas that you have to get through. It’s nice and flat and there are lots of parking areas along the way. My gps did not take me to a parking lot but when I put the trail into AllTrails I got accurate directions.
Was visiting the area and am so happy I got my gravel bike out to do this trail. As others have mentioned, it is very, very well maintained and quite smooth, enabling fast riding (I rode the entire trail as listed). As a former rail, this trail has nice and gradual elevation changes and has cool features like the tunnels and bridges. I'd highly recommend and hope to be back for another spin soon.
Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!
Short for bike, nice views, benches and even a real train.
June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.
The claim of this being a 61 mile trail is very deceptive. Almost 40 miles of this trail is nearly unrideable except for mountain bikes (and even that would be unpleasant). We are experience riders and were on hybrid bikes with wide tires and front suspension. And while our plan was to cycle 40 miles from Willimantic to E. Hampton, we only did the first 10 mile section from Willimantic to James L. Goodwin State Forest.
The trail started out as just OK, but deteriorated in less than 2 miles. After crossing S. Brook Rd, the trail the trail was extremely gnarly and super overgrown. When we reached Goodwin State Forest, we were so happy to bail out and call it quits! Luckily, we had a SAG vehicle with us so we weren't forced to cycle back over the same awful trail.
Be warned, the entire trail we rode from Willimantic to Goodwin Forest was large, loose gravel, and the scenery is incredibly boring. There are places where the trail is extremely rough. At S. Brook Rd. the trail becomes unrideable, expect by maybe some die-hard mountain bikers. We used our SAG van to pop into other points along the trail from Goodwin to E. Hampton the trail only seemed to get even worse.
Honestly, just a really unpleasant ride.
We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose
It is such a lovely trail. The view is gorgeous, either from the ocean or from the land. It goes through a few towns, all lovely and friendly. There are shops along the trail for you to stop by for ice cream, coffee or lemonade. There are a few road crossing, but the cars are very friendly and stop to let cyclists cross. The destination Bristol is just beautiful! Some areas are in the open, so the wind can be your friend or not …..
It’s a nice paved path, shaded half way through. Good for families with kids. Parking is free but though to find, suggests keep following the path till you find parking. There are several options along the way from the eastern end of the trail. Few food and restroom options, within coffee or mall shops. Public restrooms are very limited at least when starting from east end. We went only half way and back, with kids. Looking forward to finish the second half soon.
I live in Massachusetts about 25 minutes from this trail, my absolute favorite trail is the East Bay bike path, but that is about an hour drive for me, so this is one I frequent more often. I like the length of this ride, and that it is scenic, and more interesting than some of the rail trails that can be kind of boring. I think it is an easy ride, with just a few spots I need to lower my gears. I pack a lunch, snacks, and can be out for a few hours. There is ample parking, 195 Davison Ave Woonsocket is the address I use for WAZE. I have never gone as far as Providence, so I can only review Woonsocket - Lincoln.
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