Cheshire Rail Trail

MODERATE 5 reviews

Cheshire Rail Trail is a 20.6 mile moderately trafficked point-to-point trail located near Keene, New Hampshire that offers the chance to see wildlife and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

20.6 miles
1,177 feet
Point to Point

dogs on leash

kid friendly


cross country skiing



horseback riding

mountain biking

nature trips

off road driving


trail running


rails trails




Follow this incredible trail starting near Keene, NH and ending at the Massachusetts state line. The Cheshire Rail Trail is said to be the second longest rail trail in New Hampshire. It's up to you whether you ride the whole trail or just parts of it. Either way, there are plenty of diversions for hikers, bikers, nordic skiers, snowmobilers, and horseback riders. Since this trail is not paved, it is best to enjoy it when it's fairly dry or extremely snowy.Even on relatively hot days, this is a pretty good recreational trail because it has ample shade and lots of water for soaking your feet. Some highlights of the trail include the Stone Arch Bridge, near the Keene trailhead, the historic railroad remnants throughout the trail, the folksy charm of the Fitzwilliam Depot General Store, and the numerous water features along the way. If you are biking the trail, the best way to ride it is to start in Keene, New Hampshire and ride to the New Hampshire/Massachusetts state line. Unlike many of the other New Hampshire rail trails, the Cheshire trail has some good stopping spots for restocking your food and beverages. There are stores in Troy, Fitzwilliams, and at the state line. However, like most country stores, they have limited hours, so make sure to have a back-up supply of snacks and drinks. Try not to rush this trail. It has numerous spots for relaxation and tranquility. In the past, this area was visited by the likes of Henry David Thoreau and Ralph Waldo Emerson. These were well known nature buffs and contemplators. Once you spend some time on the Cheshire Rail Trail, you'll see why they chose this region for their sojourns.

22 days ago

It's not bad. Just wish there wasn't so much horse droppings everywhere in the deeper parts of it.

2 months ago

Loved this trail. Started by Kohl’s. Minor incline that was barely noticeable for the most part. Others using the trail were pleasant and polite. Trail did have a bit of litter though when you get further out. Overall a great trail! Watch out for horse poop!

trail running
5 months ago

mountain biking
Monday, August 29, 2016

Great trail for biking. Mountain bikes are strongly recommend

1 month ago