Cheshire Rail Trail South, NH

• 4-star trail
• 20 miles each way
• Moderate | Moderate gradient
• Keene - Fitzwilliam, NH | Monadnock Region
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A stone arch bridge over a river with a person riding a bicycle on top. The river has rocks scattered throughout, and the surrounding area is lush with trees and greenery, creating a serene interaction between human-made structures and nature.

The Cheshire Railroad Stone Arch Bridge.

Clearly carving a railroad line through New Hampshire hills and across wide river valleys with 1840s technology was an astonishing achievement. That remains very evident today when you explore the Cheshire Rail Trail. Cuttings through rock faces towering twenty feet above, long embankments and wetland crossings are prominent features along this route, but the jewel is no doubt the Cheshire Railroad Stone Arch bridge located just south of Keene. This masonry edifice remains strong today thanks to the placement of milled granite blocks so well engineered that no mortar was needed to hold them together.

Named for the New Hampshire county, the route of the Cheshire Railroad traced a diagonal line from Winchendon MA in the Southeast corner to Bellows Falls VT in the Northwest. The New Hampshire city of Keene sits right in the middle. This article is about the section of rail trail South of Keene. The Northern half of the trail is an article for another time.

Asphalt,

Hardpack,

Road,

No Access, ⬤ Parking Expand ↓ Map

4★ Cheshire Rail Trail South 20.3 miles each way, moderate, gain 1,200 ft (760ft S-N)
AllTrails · GPX File · Directions

Should you want to explore the full length of the Southern section of the New Hampshire's Cheshire Rail Trail as part of an out-and-back 40-plus mile journey then we suggest beginning in Keene. One could find street parking in Keene and include the initial 1 mile of asphalt paving that begins at the former central Keene railroad station, or alternatively begin at the stone arch bridge from informal parking locations on either side of US-101.

We recommend starting in Keene and heading South because after the initial flat 1 mile, the trail ascends at a consistent pace for over twelve miles. The slope is noticeable but isn't too bad as long as you tackle it at a reasonable pace. Upon making the return journey you'll thank yourself profusely for tackling the long (but gentle) uphill direction first.

A large, multi-story brick building with a prominent chimney stack extending into the sky. The building features numerous windows and a contrasting section with a peaked roof in the center. In front of the main structure is a single-story annex with a flat roof and beige exterior. The setting appears to be an industrial or manufacturing complex.

The railroads brought manufacturing industries to Keene.

From the stone arch bridge heading South the trail is managed by the NH State Park with support from the Monadnock Sno-Moles snowmobiling club. Hardpack ground under foot is also good for mountain bikes, gravel bikes and rugged hybrid cycles, though you should expect to ride over occasional embedded stones and through a couple of short sand patches. Going uphill kept us at a pace slow enough to prepare for any minor obstacles along the route. The trail alternates between wide and single-track as it crosses a variety of landscapes along its journey.

Other stand-out features along the route include several more bridges and a few trackside ponds, including the inviting Rockwood Pond which with its grassy banks to the Northwest make for an excellent swimming spot. Rockwood Pond also has a great vantage of Mount Monadnock six miles to the Northeast.

A first-person view of a person riding a bicycle on a dirt path through a forested area. The path is flanked by tall rock walls covered with moss and foliage, suggesting a gorge or valley. Sunlight filters through the tree canopy above, casting dappled shadows on the path, creating a tranquil and scenic environment.

One of the impressive hillside cuttings on the route.

Of the six former rail passenger depots along this section of the Cheshire Railroad, half remain. Keene station is located in the center of the city and is occupied by commercial ventures. Further along the route are the restored stations of Troy and Fitzwilliam. Troy station is in an excellent state of preservation, with ample parking and scheduled tours of the building. Fitwzilliam station is well preserved on the outside with the interior apparently in use as a meeting space, though vexingly the many 'no parking' signs make the town seem unwelcome to visitors.

The tree-lined Southern end of the trail across wetlands is a popular section of the route, particularly on a sunny day with good visibility. From the South end the trail is as straight as an arrow for over two miles; wide and flat with a good crushed stone surfacing. Expansive views are available in all directions as you walk among wetlands and past lily ponds while dragonflies flit by.

Trail Conditions: Hardpack trail, often single track, occasional rocks & two short sand patches. Walk bikes up four short hills.

A flowing stream with rocks and small rapids, surrounded by lush vegetation including trees and shrubs. A metal bridge with wooden railings spans the stream, supported by stone abutments. Sunlight filters through the foliage, creating dappled patterns on the water and landscape, capturing a serene and picturesque moment in nature.

Ashuelot River Bridge.

Two photographs side by side. The left photo shows an exterior view of a small yellow train station labeled ‘TROY,’ with a railroad signal post and tracks extending into the distance. The right photo presents an interior view of the station, featuring a vintage setting with wooden walls, an antique typewriter on a wooden desk, framed pictures and certificates on the walls, and an old-fashioned wooden chair.

Troy station is an excellently preserved passenger depot.

A serene lake surrounded by lush green trees under a clear blue sky. The calm water reflects the trees and sky, creating a mirror-like effect, highlighting the natural beauty and tranquility of the scene.

One of several picturesque trackside ponds along the route.

Tangents:
• Public Map at AllTrails: Cheshire Rail Trail
• TrailLink: Cheshire Branch Rail Trail
• Facebook Group: Follow, comment on this article

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