Cheshire Rail Trail

Hiking in New Hampshire

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Difficulty: Moderate
Length: 27.0 miles / 43.5 km
Duration: Full day

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Overview: 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.

Tips: - 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.
- Plan to stop at the the Depot General Store in Fitzwilliams. It is like going back in time. The store carries everything from hardware accessories to potato chips. The also have a good selection of cold beverages and a nice porch on which to drink them.

Points of Interest

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Stone Arch Bridge

This serves as the starting point for the trail, and oh what a start it is. This dry-laid (no mortar) bridge was built in 1863 and spans the Ashuelot River. Both the trail and bridge can be difficult to find. It is just SE of Keene, NH on Hwy. 101 (Marlboro St.). If you are driving from Keene, look for a dirt turnout on the right hand side of the road. There is often a car or two parked there. You will see a dirt trail going up a steep embankment. You have to go up that steep embankment to get to the bridge/trail. But don't worry; that's the only steep part on the trail.

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Troy, New Hampshire

Limited lodging and eateries are available in Troy, NH.

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Troy Depot

Constructed in 1847, the Troy depot saw such luminaries as literary giants Henry David Thoreau and Ralph Waldo Emerson pass through on their way to the Monadnock Mountain and the peaceful New Hampshire countryside.

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Rockwood Pond

Whether dipping your feet in its cool waters during a summer heat wave or viewing a kaleidoscope of fall foliage during a crisp autumn morning, Rockwood Pond is a welcome resting spot along the Cheshire Rail Trail.

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Fitzwilliam, New Hampshire

The Depot General Store, in Fitzwilliam, NH is a New Hampshire tradition. You will fall in love with the ambience, the eclectic inventory, and the homey porch out front. Even if you're not hungry or thirsty, you should stop and take a look at this slice of Americana. It is a quintessential New England general store.

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Collins Pond

This is one of the many water features found along New Hampshire's Cheshire Rail Trail.

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railroad cuts

In various spots along the trail, you will go through a narrow gap in the hillside with steep rock walls on either side. This is where they chose to cut through a hill instead of go over it or around it. This was more difficult and expensive to build, but saved operating costs once the railroad began running.

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streams, bridges, brooks, ponds, and creeks

From beginning to end, the Cheshire Rail Trail is defined by its abundance and variety of water features.

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forests and marshlands

The forests provide shade on hot summer days of riding and hiking the trail. The marshlands provide an abundance of wildlife and scenic beauty.

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Massachusetts State Line

This is the end of the Cheshire Rail Trail, but never fear. Whether you turn around and retrace your tracks or you continue into Massachusetts, there's more great trail fun either way.

Pictures in this guide taken by: trailsnet, Stone Arch Bridge near Keene, NH, Cheshire Rail Trail, trail going up to bridge, Troy, New Hampshire, Cheshire Branch Rail Trail, Troy Depot, Rockwood Pond, Cheshire Rail Trail food break, Enjoy a cold beverage on the porch at the Depot General Store in Fitzilliam, NH., Cheshire Rail Trail staple, This chipmunk took a break from guarding the trail to have a snack from the Depot General Store., Cheshire Rail Trail.JPG, Collins Pond on the Cheshire Branch Trail, Cheshire Branch Trail, abandoned railroad grade, trailside water features, Fall colors are just beginning to decorate the New Hampshire landscape.

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