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.

Length20.6 miElevation gain1,177 ftRoute typePoint to point
Dogs on leashkid friendlyCross-country skiingFishingHikingHorseback ridingMountain bikingNature tripsSnowshoeingWalkingBird watchingRunningRails trailsViewsWildlifeSnow
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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.

The surface of this trail is gravel, ballast, dirt, and an occasional sandy spot, so you'll want fairly wide tires on your bike. A road bike probably wouldn't do well on most portions of this trail. The water features along the way are beautiful, but may also serve as breeding grounds for insects. Bring insect repellent just in case. Be prepared for possible bike malfunctions. You will not find bike shops near the trail, so have spare tubes and other biking accessories.

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Reviews (47)
Photos (69)
Recordings (42)
Completed (71)
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Mary Woodruff
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Hiking
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Alvah Stone
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Mountain biking
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Kal L
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Mountain bikingGreat!

Had a beautiful ride from Rockwood Pond, headed south to Rt. 12, stopping at the trail terminus, just above the state line. We were three adults and two kids (10/7), and we all managed the 18 miles just fine on hybrid bikes. Trail surface varies from dirt, to sand, to rocky patches. It’s mostly flat, with a few rises and dips near road crossings. We only saw a handful of people in the trail, and the scenery was varied and lovely the whole way through. We refueled at the State Line Smoke Shop on Rt. 12 with water and snicker bars before making our way back. There is definitely parking at the trail end, and at Rockwood Pond, but parking at road crossings seems otherwise discouraged.

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Kavya Rani
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HikingGreat!

Some parts of trail are not maintained. But it offers well maintained paths near by the city. Parts of the trail which run through the city have are high traffic. But if you come to the outskirts of the city, traffic is moderate. We mostly hike the trail that goes from Whitcomb Mills Road to Dickson road, which is low to medium traffic, well shaded and well maintained. We love this trail.

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Amber Stocking
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Bike touring

Not a clear continuous route...

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Erin Trombley
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HikingFlooded

My mom and I walked this trail in segments. We started by the stone arch bridge and walked towards the Mass line. There are some really beautiful parts of this trail. Really cool to think of a train going through here. We would walk about an hour , mark where we stopped and headed back. There are plenty of places that meet up with roads so you can pick up where you left off. Definitely recommend bug spray and pay attention to what the weather was the day before. Some parts of this trail gets very muddy!

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Holly Millslagle
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HikingBugs
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Derek Jones
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Hiking

Departed out of Keene south. I had high expectations this would be like the Chief Ladiga Trail in Alabama… I probably should have gone north, but decided to go look at the bridge that the state parks video advertises… After about a mile or so of paved path, the trail abruptly ends! Where’s the bridge? I continued to parallel the path which required me to walk through a neighborhood since the old railroad path is purposefully overgrown and blocked. (To get back on it would have required trespassing on private property.) When the State Parks advertisement says “be careful crossing the road” to get to a pinnacle view of the old bridge, they mean it... no markings, no crosswalk, no pedestrian crossing sign, etc. to go beyond that bridge eventually requires you to go around gates. I’m not a gate crasher. Had hoped to get in a 6 mile out hike (12 total) and barely got 4 miles total. It’s on me for not asking around, but the portion I was on out of Keene was nowhere near what is advertised. Overall, the hike simply turned into a walk workout.

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Ceara Comeau-Rosello
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MuddyRocky

Excellent trail for a great workout! my dad and I biked this trail starting from the Stone Arch Bridge and went about five miles up. (2.5 miles from Troy). We plan to bike the rest of the way over the next few weeks when the weather allows for it. A quick note to any other cyclists: there are several areas where the trail has sand, mud, and good sized rocks that like to hide. Be sure you have good (off road) tires just because of the terrain and going from the Bridge to the Mass boarder is a subtle uphill trek. But all in all, we loved it. We got to explore some really cool areas that had remnants of the railroad!

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Robert Bowen
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I highly recommend it. The trail does not allow motorized vehicles other than skimobiles during the winter. Marked on all gates.

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

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Heather King
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Hiking

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!

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John White
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Running
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daniel coury
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Mountain biking
First to Review

Great trail for biking. Mountain bikes are strongly recommend

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Rich Blanchard
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Hiking
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Jeff D
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Hiking
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Alexis Chesney
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Hiking
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Andrey Zawadowskiy
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Hiking
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Michele Griffin
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Hiking
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Seth Reece
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Hiking
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Mallary Reece
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Hiking
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Emily Mousette
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Mountain biking
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Emily Mousette
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Hiking
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Emily Mousette
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Mountain biking
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Emily Mousette
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Mountain biking
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Darleen Frances
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Hiking
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Lia Tyler
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Mountain biking
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Jean Driscoll Dennison
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Hiking
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Darleen Frances
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Hiking
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