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Cheshire Rail Trail

Follow this incredible trail starting at the Stone Arch Bridge near Keene, NH and ending at the Massachusetts state line
Difficulty: Moderate
Length: 27 miles
Duration: Full day
Family Friendly

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 ... more »

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... more »

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Points of Interest

1. 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 ... More

2. Troy, New Hampshire

Limited lodging and eateries are available in Troy, NH.

3. 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.

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.

5. 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.

6. Collins Pond

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

7. 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.

8. streams, bridges, brooks, ponds, and creeks

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

9. 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.

10. 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.