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 55 trails covering 409 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.
A sidepath has been constructed adjacent to Route 189 to Main St in Tariffville. Trail is now about 3 miles long. It will be designated as part of the East Coast Greenway and is visible on Google Street View.
After reading many of the mixed reviews for this trail on TrailLink, I decided to keep my ride short but sweet by restricting it to what seemed to be the most picturesque - the portion between the historic Unionville train depot and the Riverside Nursery and Garden Center in Collinsville.
This part of the trail contains breathtaking views of the officially deemed wild and scenic Farmington River. In addition, since I did this in mid October, the river was a perfect reflecting glass for the amazing fall colors.
My ride was only a total of twelve miles out and back, but I now have the most perfect photos, videos, and memories of this Connecticut treasure!
The bike ride is easy and mostly flat with lots of locals getting their steps in and exercising their dogs. Surprisingly, I only encountered two other bicyclists on my early weekday morning ride.
We love biking the Airline and have used non electric hybrid bikes as well as e-bikes. Both work well. On 10/28/2023 we biked the section from Willimantic parking at the Connecticut Eastern Railroad Museum area and pedaled to Rt. 207 Lebanon Rd, Amston, CT. FYI, we're in our 60s and encountered no difficulties with the terrain.
I rode the southern half of this trail from Millerton to Wasaic the first week in October on a 75° afternoon. Beautiful ride on a beautiful day.
Nice quiet ride to take time to enjoy these beautiful days.
This is still a great trail but currently (9/2023) the Trailway is closed between the Stormville parking area on South Green Haven Road and the road crossing at Depot Road due to a partial washout (see pic).
There is a bypass using Route 216 (busy and not always good shoulders).
People have gone around the barricades and used the Trailway. Please use caution if you do so.
Rode the 13 miles from Orphan Farm Rd to Millerton and back. At the northern end, at Orphan Farm Rd is a large parking area adjacent to a small farm, a solar panel field and a glamping site. No one there at 8am that Saturday but half a dozen cars upon my return at 11. Likewise, I had the trail practically to myself until I neared Millerton and found it moderately traveled by later that morning. The asphalt trail was in very good condition and there are a few boardwalk sections as well, also in very good condition. The environs are beautiful with forested sections, farm fields, wetlands and vistas of the nearby hills. Not more than two miles from the north end is the Depot Deli, near the entrance to Taconic State Park, where all manner of beverages, ice cream and snacks can be found. Breakfast at Oakhurst Diner in Millerton is highly recommended. Clean public bathrooms can be found just behind the schoolhouse museum beside the trail after crossing the main street.
Very nice 7 miler tonight just before sundown. Trail was very clean and only lightly populated as we headed south for 3 1/2 miles and then back to the parking lot.
Too bad that Daddy O's had closed their kitchen when we returned. Had to go to the Redline Diner to get a post-ride meal on a Sunday night.
Road crossings were well marked and use automatic yellow flashing lights for traffic to be aware of bikers approaching the crossing. A nice feature.
I think folks have to temper their expectations. This isn't the Farmington Canal Trail and isn't trying to be. This is a nice, well paved track for exercise and actual transportation. It provides a bike link from Newington and the southern end of West Hartford to downtown New Britain that previously didn't exist. For that I'm super happy. West Hartford has a decent bike network that connects into Hartford, so now there is a semi-cohesive bike network that spans from downtown Hartford all the way to New Britain with stops in between. New Britain is booming (by New Britain standards) so there's actually a lot to visit at the end of the trail, like the art museum, breweries, restaurants, etc. I wish the Multi-Use Trail extended all the way to the Elmwood or even Hartford stops, but it's useful the way it is now. It's not all that scenic but there's still a decent amount of greenery and it's pleasant to ride. It's next to the busway and train tracks, but the train is relatively far away, and the buses are not noisy or especially polluting (they are hybrids).
The bridge is repaired and the trail is open.
So amazing to be back on our bikes again. The hubby and I tried this trail for our first with our new bikes. Smooth ride… great views over the Westfield River. Definitely one to try when going out for your first ride!
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
