Explore the best rated trails in Middletown, CT. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk. With more than 55 trails covering 395 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.
Bring a hat for windy days . Beautiful walk . Access to McCook park is up the hill if you want a longer walk.
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.
Paved trail, it’s clean, 10+ miles long. Well maintained. Great views and you may see turkeys, deer and ground hogs/ gofer not sure what they were. There are bugs out that will hit you in the face and stick to your body will riding
The trail is so boring only 1 biker in the entire trail
Very nice fully paved trail. Saw some gophers and deer along the way. Maybe an eagle too but not sure. Might have been a hawk or a vulture. Parked at senior center as recommended in the trail information section.
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