Southern section very rough, significant ATV use (officially sanctioned). Washed out slopes can be unsafe with large cobbles, exposed bedrock, and washouts. If you manage to escape the ATVs it's quiet.

I live about 7 miles from the South Londonderry trail head and only wish the trail was better suited for my hybrid bike. The first 3 miles (approx) to the Winhall campground are in bad shape (dirt festooned with rocks, roots, ruts and mud puddles). I don't know when the article summary was written, but I have a different idea of what "well maintained" means. Those with mountain bikes or fat tire bikes should have a much easier time with it though.
The trail ride is sandwiched by a campground road for a couple of miles. It's asphalt, and other than navigating several speed bumps, is an easy ride to another dirt path on the Jamaica side. It's in better shape than the South Londonderry portion. It's not in great shape for riding either but very manageable.
The two dirt path portions follow the contour of the tree lined West River. The view is particularly vivid, particularly in Autumn, and a favorite spot to hike with my dog. As a bike trail though, it needs work.

This was a bike ride from Depot Street in Hinsdale to Keene State College area. Beautiful views of Ashuelot River along ride and several covered bridges. Several old mill buildings in various state of disrepair to look at. The trail from Depot Street to near Riverside Lane in Swansey has good sections of loose gravel with several sections of puddles and mud. This part of the trail is good for mountain bikes and for those that don't mind going through puddles that vary in length from a few feet to over 20 feet long. Some are deep too. A few potholes and gopher holes in this section and one bridge with bad decking boards. I'd rate this first section of the ride a 2. From Riverside Lane up to Keene trail is wide with good gravel base. Easy for most bikes to navigate this. I'd rate this section a 4.

This trail is a lot of fun! Mountain bike is the best! Lots of railroad stuff to see!!!

Excellent ride into Jaffrey! Nice wide trail, well maintained by local snowmobile club. Pleasant views along conservation areas.Far end towards Rindge was a bit more technical with many rails still in place.

The trail was in good shape. Unfortunately there wasn't much to see. The highlight was the trestle over the Sugar River. The place where the trail 'parallels Washington Street' was busy and care was needed because many cars were entering the shopping area.

Since the trail was short, we continued on the Sugar River trail. There was a fair amount of working being done on it and it was not as nice as it was one year ago. Sand was being added in places which made it more difficult to ride through. Overall, however, we'd recommend the Sugar River trail west side and make sure you see at least one of the two train covered bridges!

With touring version of an e-bike, found this trail to be interesting, historic, and fun! Yes, there are some spots with sand, but if one rides smart, no issue. Did not run into any of the ATV’s mentioned in the other reviews. Loved all of the River crossings, as well as the two covered bridges! Loved the white tailed deer seen on the route as well!

I have hiked and rode horseback on the Cheshire rail trail needs to be welcome signs for hose trailers somewhere!

This is a nice (mostly flat) trail that is paved from the road behind the Clark YMCA all the way to 140. There is a short on-road section with a decent uphill to pick up the trail over by Rt 140. Past 140, the trail alternates between sand, gravel, and loose rock on one uphill. Trail suddenly ends at a barrier that’s the edge of a cemetary.