Explore the best rated trails in Woodbridge, CT, whether you're looking for an easy walking trail or a bike trail like the Shoreline Greenway Trail and Charter Oak Greenway . With more than 63 trails covering 531 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.
Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!
Wonderful trail. Part of the larger Empire State Trailway. This part from Eastview to Baldwin Place is the section I ride the most. Mostly shaded once you're north of Millwood with plenty of spots where you can stop for a bite or veer off for road riding near the reservoirs.
The trail is not accessible for a 3-mile stretch. From Green Haven and then Eastbound is impossible to pass. Trees have fallen down virtually every 50 yards blocking passage. I carried my bike past about 6 trees and each time I saw another tree blocking the trail. I came across a clean up crew that told me the downed trees went all the way to Green Haven. I was 3 miles east of Green Haven when the mess started. There is also debris along the entire section which I was fortunate not to get a flat tire. The cleaning crew told me they have only 4 people and they will try to hire a contractor to clear the trees. There is no way a crew of 4 people could handle this. It would take them months to clean it up. (July 10, 2026)
The Trailways Bridge over the river in Brewster is open, eliminating the on-road detour. The eastern end is currently at the NY/CT line at Farrington Woods (with trail parking) in CT. Long range plans are to develop the CT portion of the RR path to Danbury.
There are far more legit parking areas than currently shown on TrailLink. Services are few and some might seem close lack easy access from route to road. High point is Whaley Lake. The trail is in good condition for it's entire length.
Great ride. First time on a gravel surface and found it pretty easy going with a few rough spots. It rained the night before and early morning, so I wasn’t sure what to expect. Trail was damp but no big puddles. I took in 28 miles of the 40 out and back. Will do it again and try to get the whole distance.
Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.
Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.
I did this route many times. About a half mile West from the South End of the Bethpage Bike Path ie,. Merrick Road NY 27A, you’ll see the Wantaugh Parkway entrance to the Jones Beach path. way back when they couple
This trail was OK. The part along the river and in downtown was scenic and it was paved all the way.
However, it goes along the highway for a while with just a chain link fence as separation, which is not enjoyable at all (east of the gap is not scenic). It also has a lot of tree roots creating speed bumps. Finally, the gap between the river and the rest is significant (& don't take what looks like the most direct route as Pratt & Whittney has a security gate for part, so you can't get through unless employed there).
Why has this trail not been plowed?? It has been snowed over since December.
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