Explore the best rated trails in Plymouth, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 53 trails covering 435 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.
The Harlem Valley Trail from Taconic State Park to Wassaic (Metro North Station) spans 24 miles through beautiful farmland and marshy areas with Mountain ranges on both sides (Berkshire and Catskills). The entire trail is paved with asphalt. Unfortunately, there are older segments that sorely need maintenance, especially the roughly 4 mile stretch from Taconic State Park south. The trail is also narrow in spots making it uncomfortably close for bikes traveling in opposing directions. The trail does pass through several towns where you can find places to eat and shop.
We biked from Simsbury to Farmington on the Canal trail. It was nice with the fall color, but there is not much else to see. On the way back we took the River trail. It goes parallel to the river and it is very pretty. It goes thru Canton, which is a charming little town. From there the bike trail is quite good for a while, but then you have to bike on the road. The bike trail sign is painted on the road, but you have to look for it. Traffic was not bad at all. The last part goes thru a simsbury park, there are a lot of roots, gotta be careful. All in all the river trail is very nice, even with a couple of miles of in road biking. there there
Beautiful for a bike ride in the fall. The trail is well kept, the views are beautiful and is moderately trafficked. I started at the Manchester trailhead and just kept going straight, passing parking lots in Vernon and Bolton. Didn’t notice much options for restrooms or pit stops for food so plan accordingly.
Although it's an easy, beautiful, and relatively flat trail overall, the Naugatuck-to-western-outskirts-of-Naugatuck part of the Larkin Bridle trail is a little more challenging, isolated, and wild, whereas the west-of-Naugatuck to Southbury part of Larkin Bridle is wider, flatter, and more accessible.
Personally, I am not big on technical/single track bike riding, so I experimented with Larkin Bridle until I found just the right section to become my regular ride. For me, that's definitely the flatter, wider, less technical portion. These coordinates (41.474814, -73.117086) will take you to a very quiet, non-residential road with a turnout that allows for three or four cars to park in front of the wide gate that marks the path. (There's a marshy pond nearby where you might hear ducks quacking.) This is the point on Larkin Bridle where it become an excellent trail not only for comfort-minded fitness bike riders like me, but also a great walking path, especially for my dad, who is older.
From the coordinates above to Southbury it is about 5.5 miles, one way. You'll be on a wide path with a mix of hard pack dirt and gravel. Very easy and flat, unless it's been raining for a few days, in which case some parts can get a bit muddy. Overall, this part of the path is shady and well maintained with beautiful, tall trees, occasional bodies of water, and interesting rock formations. Just gorgeous! On this part of the trail, you can relax and pass people easily. Would be wonderful for a post-Thanksgiving dinner walk or a ramble with the dog. The Naugatuck-to-western-outskirts of Naugatuck portion of Larkin Bridle, by contrast, while still very doable on a bike, is much more weedy, woodsy, and rocky, with brief portions that have very steep ups-and-downs near road crossings. For a more relaxing experience, I recommend the west-of-Naugatuck to Southbury portion, starting at the coordinates above and heading toward Southbury.
Rode Plainville CT to CT/MA border. Northern section. I like that you go through many towns on the lower half then out in the country from Simsbury north. Beautiful scenery. Paved the whole way, some sections with roots coming through.
While the portion along the River is nice. The upper half from Simbury to Canton is terrible. Mostly on road, 10% grades, poorly marked. We had to use rail to trails app and use GPS so we did not get lost. I’d rate it one star but the Canton to Farmington section is nicer. Stick with the Farmington Canal Trail only if your visiting from out of town like we were.
The trail is so boring only 1 biker in the entire trail
I lived in Poughkeepsie for 5 years in the early 2000's and I used to imagine how awesome it would be to convert some of the abandoned rail lines that criss-crossed the city and the region. Since then, they have done exactly that and I find that the William Steinhaus Dutchess Rail Trail is the best trail I've ridden yet! It is a nice easy trail, and with plenty of other bikers, walkers, joggers, etc... It is excellent how the trail links up with the walkway-over-the Hudson (which was simply an abandoned hulk when I lived there!) and the Maywood Rail Trail to the south. County Exec. William Steinhaus, et al - great job!
I lived in Poughkeepsie for 5 years in the early 2000's and I used to imagine how awesome it would be to convert some of the abandoned rail lines that criss-crossed the city and the region. Since then, they have done exactly that and I find that the William Steinhaus Dutchess Rail Trail is the best trail I've ridden yet! It is a nice easy trail, and with plenty of other bikers, walkers, joggers, etc... It is excellent how the trail links up with the walkway-over-the Hudson (which was simply an abandoned hulk when I lived there!) and the Maywood Rail Trail to the south. County Exec. William Steinhaus, et al - great job!
I went to ride this trail for the first time from New York State. It was fair at best. It’s probably fine for folks who live there and know where to go when the actual trail ends. Being it was my first ride there, I could have used a couple of signs to direct me in the right direction. I got to Collinsville and had no idea where I was going. Finally gave up and went back. It could use a little maintenance along the River where the tree roots break through the pavement. Not impressed.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
