Explore the best rated trails in Cheshire, 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 54 trails covering 405 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.
It’s a beautiful trail. BUT, please beware of the yellow post they have installed at all the road crossings to keep motor vehicles off the trail. As I was crossing the road at one of the crossings, as I came back onto the trail my handlebar caught the post and sandwiched me in my bike and the bike and I went down hard. I ended up fracturing my back. So please be careful on this trail through Southwick.
I do my run here a few times a month, It is so beautiful I really like it. It is so green and right next to the CT River the air is so clean. It's good for a long run where you can get up to 10 miles and it's a well maintained trail.
I’ve completed the Wilton trails in Lovers Lane, Entrance near Orem’s Dinner and Mathews Park. All are great. My favorites are the Wilton Trails, you enter and your engulfed in nature. Absolutely beautiful. I also love walking In Mathews park although that is more of a city trail to me not as much nature as these are concrete paved and you pass near traffic and such. So grateful to all the hard work put into to providing these trails thank you!
I rode the Northern section of the trail, (the section north of rt 5 and on the east side of the river) so this review is about that, and how I got there. The trail appears to be nice and well maintained, it is in a larger city so it does have some city issues, but I always felt safe. Views are mostly of the Connecticut river and the rail line, Basketball hall of fame doesn't really look great from the trail, and the park along the trail is less interesting than the river itself. If you like looking at railway infrastructure that is still in use this trail will not disappoint either.
I used the Springfield train station to get food, drinks, and use the restroom, there was enough room to easily get my bike into the bathroom.
I took the Hartford line train from Wallingford CT to get to Springfield and I was really happy about how easy it was to do that, YMMV as CT line staff are being lazy and not opening the bike rack doors on some trains. I did this trail mostly to see how easy it is to take the train to the trail and I was happy with that part of the trip.
I rode this over two separate weekends, Once from the Wassaic train station to Millerton, and once from Millerton to almost the end of the trail. Picking a favorite section is a really hard call, they both have their pluses. One of the things I really liked is the lack of level crossings making this more of a bikers trail than a walking trail with a lot of trail where you will only see bikes for a few miles. Pedestrians are great, with only bikes there is a lot less stress about passing. I think just about every level crossing has a portalet, even the ones without parking.
Wassaic didn't offer much in the way of attractions or close by food, Millerton on the other hand had plenty to offer and explore, there is even an actual bathroom on the trail in Millerton. While it would probably be fine to bike the town, I used the rack and walked it. Lots of interesting shops and food options in Millerton so it is worth stopping. Once you head north of Millerton you are back in open land with the occasional road crossings. There is a section where you ride over a large pond on a bridge that is nice.
Walked this trail on 10/22/2022 and while it is a nice bike able trail, there are a few problems. I noticed that a few of the bridges are a couple of inches higher than the trail surface, and I'm not saying a little bump, I'm saying stop and walk it or fall off your bike bumps. Other than that this was a really nice trail and I would bike it with caution, or a mountain bike. Fall colors were amazing while I was there.
Bring a hat for windy days . Beautiful walk . Access to McCook park is up the hill if you want a longer walk.
Yes the path is new, surrounded by greenery and tuck back from the main road. My biggest complaint is the amount of crossroads at the beginning in smith town. Too much interruptions AND You really need to be careful even when you hit the rider alert button for crosswalks The ride itself is nice, but no facilities on path.
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.
This trail is great despite the middle aged men speeding past you at 90 mph on their LeMonds. I’m not sure if they are bike messengers or just “has beens” trying to live out their dreams of being in the Tour De France, but their speed and shrill shouts of “Left, Left, Left!” piercing the crisp fall air can really ruin what is otherwise a beautiful and relaxing family outing.
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
