From Railroad to Rail Trail: A History of the Cheshire Recreational Rail Trail

This photograph circa 1951 captured a train traveling on The Cheshire Railroad and crossing Keene’s famous arch bridge. Photo courtesy of The Cheshire Historical Society.

At 160 years ago this month in the small town of Keene in Cheshire County a large crowd gathered on Main Street eagerly awaiting the arrival of something most of whom had never seen or experienced before. More than 5,000 people lingered in joyous anticipation, all seeming to concentrate around a specific crossing of newly-laid railroad beds which split through the crowd across a dusty Main Street. The date was May 16, 1848 and the first train to reach Keene was en route from Boston. With the train’s entrance came the birth of one of Cheshire County’s most prized man-made marvels, The Cheshire Railroad.

This photograph from the mid-1940s to early-1950s shows a train pulling into the Keene station. Photo courtesy of The Cheshire Historical Society.

When the Cheshire No. 5 and the Monadnock No. 6 doubleheader train rolled over the famous arch bridge and pulled into Keene station that day in May of 1848, the town erupted into applause and celebration. Historian and photographer Marium E. Foster wrote of the event:

“The train was decorated its entire length with flags and evergreens. As it came around the curve from Water Street crossing and into the depot, cannons roared and bells rang amid the cheers of over 5,000 people. The train brought Mayor Quincy of Boston … and other prominent men to the celebration. The Boston Suffolk Brass Band volunteered for the occasion and led the procession of stockholders from the depot to the Town Hall for a business meeting, after which the band led the stockholders back to the depot.”

According to historian Donald B. Valentine, Jr., one older crowd member reportedly looked skyward and yelled. “Now O Lord I am ready to go,” after witnessing the train’s arrival.

Nowadays, the railroad is gone after closing for good in the early 1960s due to the improvements made to New England highways and roads. However, to this day, 50 years after closing, the rail bed still exists and inspires. The Cheshire Recreational Rail Trail, as it is known as today, is a hugely popular attraction for historians, bicyclists, hikers, walkers, as well as other recreationalists.

As one who has always been interested in recreation and how it relates to history, I decided to take my bike and my girlfriend on a historical endeavor, coasting on the trail just as a 19th-century train would have done. Although the railroad used to extend over 50 miles from South Ashburnham, Massachusetts to Bedford Falls, Vermont, the recreational rail trail was cut shorter, running from South Ashburnham to southern Walpole, New Hampshire. On its way, the trail passes through Fitchburg and Winchendon, Massachusetts until it crosses the state border into Fitzwilliam, New Hampshire. From there it continues northward alongside Route 12 through downtown Troy, Marlborough, Swanzey, and Keene.

If you have a whole day and you love adventures, taking on the entirety of the Cheshire Recreational Rail Trail would be a perfect way to spend the day (map). Since we didn’t have the whole day, we decided to start at a trailhead off of Route 12 in northern Troy and ride through downtown Keene. It was all downhill from there! (literally)

My favorite part of the trail — these ravines, which were spotted along the trail, served as the best pick-me-ups. The air was calmer, less humid, and much cooler because the breezy wind current is consistent. Very nice for snack breaks.
A piece of the railroad still sits along the trail.

When we reached the arch bridge in Keene, we were somewhat exhausted, but from here-on-out it was smooth sailing over paved trails. After we cautiously crossed Route 101, we drifted into downtown Keene via the trail across from the arch bridge. This is the portion of the route where road bikes work best.

Cyclists check for traffic before cautiously passing through Route 101 to the trailhead at the arch bridge.

After following the beautiful Industrial Heritage section of the trail in eastern Keene, we arrived on Main Street. Obviously, when she and I crossed Main Street, Keene’s reaction was not as jubilant as it was in 1848 when the first train came in. We received no outpour of applause or cheer. Only the faint sounds of conversation, the springtime buzz of Main Street business, and the intermingling of car horns and revving engines. Nevertheless, we carefully navigated through Main Street by following Railroad Street across to the concrete path crammed between Margaritas and Corner News.

In this part of the trail, her road bike outperformed my mountain bike. So I followed her for most of this section.

The path continued alongside Gilbo Avenue, then cut through the Colony Mill parking lot past Elm City Brewery (which has killer burgers if you’re up for a break). After the parking area, we crossed Island Street onto the Cheshire path marked by a sign.

Still way behind her. Chugging along.

From there, the path leads to a bike and pedestrian bridge above the highways in west Keene.


After the bridge, the underdeveloped trail gets rough again cutting through granite cliffs where the towns of Westmoreland and Surry meet with northwestern Keene. It then continues onward until ending at the junction with Route 12 in Walpole.


The Cheshire Recreational Rail Trail started as an essential link for the Keene economy. Although the railroad’s decline and demise is unfortunate, the rail bed still lives on. I’ll conclude with this quote below from Donald Valentine, Jr., which best summarizes the Cheshire Railroad:

“It was a prosperous shortline run by thrifty local Yankees which formed an integral part of a through route. It never required a roster of more than thirty three locomotives at one time and these were well maintained in its excellent shops. It had the foresight to modernize or change when it was obviously to its advantage or going to be required eventually for reasons beyond its control.”

My favorite part of the trail was feeling the cool breeze between the massive cuts through granite in northern Troy. What’s your favorite part of the Cheshire Recreational Rail Trail?


Andrew Reynolds

Howdy folks! My name is Andrew Reynolds. I've lived in New Hampshire for more than 4 years, and I recently graduated with a B.A. in Journalism from Keene State College. To put it simply, I'm a writer and photographer who loves everything about the outdoors--including but not limited to kayaking, mountain-biking, fishing, swimming, camping, backpacking, hiking, rock-climbing, picnicking, walking the dog(s), and meditating at a peaceful vista. If I had to describe myself (and, therefore, my blog) in three words, I would choose the following: curious, adventurous, and quirky. I think curious fits because of my interest and passion in learning and education, which pushes me to research on my own as well as talk to the experts about the science and history behind our environment (ecology, geology, biology, astronomy, etc.). Adventurous is representative because of my everlasting wanderlust and dedication to adventuring to the state's countless "hidden gems," tranquil day-trips, and other interesting escapades. Lastly, but most importantly, I chose quirky because of the perspective I like to offer through this blog. Being disconnected from our natural environment has intense consequences, not only for our personal health and sanity, but indirectly for the well-being of others--present and future. One of the biggest reasons for why I enjoy the outdoors so much is because it's the most satisfying way for me to break out of the bubble, stray from the hustle-bustle, and gather a fresh outlook on what's truly important in life. I hope that documenting and sharing my experiences in this blog will serve as a vehicle to inspire more people to understand, care for, and appreciate our environment, as well as the health of our planet and its inhabitants. Happy (and safe) trails everyone!

5 thoughts to “From Railroad to Rail Trail: A History of the Cheshire Recreational Rail Trail”

  1. Great article and pictures. Thank you! It looks like a great place to ride on a dry summer day. It really is wonderful how folks are banding together to convert these old railroad beds into beautiful scenic paths. If you listen closely you will be able to hear the steam belching from those iron horses as they pass through those granite cuts.

    1. Nice article! Looking forward to experiencing trail.
      Just for the record, the Cheshire Branch witnessed it’s last train in 1972.

  2. The northern end of the Cheshire Rail Trail has been greatly damaged by the local business which has made a commercial cut across the trail in Westmoreland and Walpole. Someone should take a serious look at this.

  3. When I was a young boy, my family lived in Westport. Periodically, my mother and I would board what was locally known as the “putt-putt” and go into Keene for shopping. I can only guess that the putt-putt was operated by the Ashuelot Railroad?

    Do you have any information on the putt-putt? The time period was 1945-1948.


  4. PLEASE, Andrew Reynolds, help us protect this more northernly section of The Historic Cheshire Rail Trail, on the Westmoreland-Walpole town line… this section, abutting our property, includes the Historic 1840’s Aldrich Brook Stone Culvert – unique in that it includes the 1840’s road to Walpole upon its western end (video found here , which also shows the 1927 Old Route 12 ) – and we also hold historic 1848 easement rights in our property deed to a relatively rare, and deeded, 1848 Farm crossing and granite-block Cattle Underpass (all eligible for listing on The National Register of Historic Places) – All the Citizens of New Hampshire need to support this cause, protecting Public interests in Public lands, and the Public’s Heritage…

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