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

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!

Really nice trail! Very much enjoyed the ride. Would highly recommend

Finally did what I wanted to do for years. Biked from Northfield using the Lake Winnipesaukee trail to the Northern Rail Trail to the Fireside Inn in Lebanon NH. This was a weekend bike trip I wanted to do for a long time and had the perfect weather. My suggestion if you are going north and want to connect to the Northern Rail Trail instead of back tracking I would take Chance Pond Road. Once you go up the road a little cut to the right before the bridge going across the road. That bridge is part of the Northern Rail Trail. The hill to get to the bridge is quite steep so I recommend to walk the bike. Once on the bridge free sailing. My half way mark was the Danbury Country Store. They are very friendly to bikers and if you have an ebike they have a charging port on the right hand side of the store. Also have a deck on the front of the store with tables and chairs where you can have a meal while the bike is charging. Deli inside to grab something to eat.

Will say the more north you go the rougher the trail becomes. Some spots is an overkill of gravel that is very loose. Not very safe where you are trying to keep your balance and difficult to get any speed. Other than that a lot of lakes and scenery along the way. If you are using Google Maps along the trip it will suggest to get off the trail for 2 miles and get back on the trail. I recommend to stay on the trail. The fireside inn in Lebanon was about 1.5 miles off the trail and the hotel is bike friendly. You are in walking distance of a Walgreens and restaurants near by. Also there is free breakfast in the morning. A lot of off ramps along the trail for eatery which I believe was set up for snowmobiles in the winter time but if your bike has good suspension they are usable for bikers also. If you are using an ebike like I was the trip is durable as long as you save your power on the inclines and heavy gravel spots. The Danbury Country Store is ideal for charging as you take a break.

There is one spot on the trail you want to be careful on. On the way back past Enfield there is a steep incline with a pond to the right of you. To your left is a metal frame for a bridge and the trail is very narrow and a blind turn to the left. If someone was coming my way it would of been a major accident. I can't stress enough to be careful there.

Overall a fun bike trip if you are up for the challenge. I could of done each day trip within 5 to 6 hours but decided to take my time and do a lot of stops along the way and take pictures. I recommend to do the same.

We had a great time riding and taking in the scenic trail. Loved riding along the river. Took a picnic lunch and stopped to eat.

Thanks to Jimbo's review, we lowered our expectations for this trail and had an enjoyable ride. We parked in Granville, NY, and took the trail southerly into Vermont. In NY, the trail includes stretches of grass, packed earth, and well-packed gravel. In VT, it switches to gravel. It certainly wasn't paved asphalt, and the ride had more vibration and required more effort than it would have been on a paved path, but riding our hybrids, we did not find it excessively bouncy, or even particularly uncomfortable. And although there were horseshoe prints, we didn't see any deep divots. At the same time, the ride passes through beautiful countryside and tidy farmland. We rode it on the Monday of a 3-day holiday, and saw virtually no one on the trail.