Explore the best rated trails in Thompson, CT, whether you're looking for an easy walking trail or a bike trail like the East Bay Bike Path (RI) and Mystic River Greenway . With more than 87 trails covering 676 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.
Had a great evening bike ride out at the Windsor Locks Canal trail earlier this month (Aug, '25). The trail is paved, and as others have mentioned, it is not super smooth in some areas where the tree roots are pushing the asphalt up but can be navigated pretty easily. I was riding my gravel bike setup with 42mm tires and was able to go quite fast - averaging 15mph on the ride so it really was not that beat up / bad.
The scenery on the river is very nice, and the canal on the other side was also fun - lots of wildlife to see. Would recommend if in the area!
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.
My husband I decided to ride this trail on our visit to Boston. We parked at 31 McKenn Street in Waltham and rode in towards Boston, then crossed the river to ride back on the other side. First, I'll start with the positives. It has areas with nice shade and the views along the river are neat. Now for the negatives. The trail boasts it is all asphalt. It is not. There were many spots with packed dirt surface. Even though I don't like riding on anything but asphalt or concrete, this at least was pretty smooth and level. NOT compared to the badly maintained asphalt and concrete. The vegetation needed to be trimmed, the path was NOT marked at all (luckily my husband had a map on his phone), many sections were very narrow, not wide enough to have two bikes pass and the asphalt had many cracks that I had to be careful to watch for. Sorry but whoever has the contract to maintain this trail is falling down on the job. Boston is such a neat city so I won't let this trail color our experience as totally bad, but you couldn't pay me to ride this trail again.
Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.
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
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