The Cheshire Rail Trail follows the former grade of the Cheshire Railroad, an early carrier established during the 1840s. It completed the corridor later that decade, reaching as far west as Bellows Falls, Vermont, just across the Connecticut River. The Cheshire was later acquired by another company and eventually wound up as part of the Boston & Maine’s expansive network across New England. Because of the time period in which it was built, the line saw more than a century of service. Declining traffic and business hurt the route in the postwar years, although it was a vital connection with the Rutland for many years until that railroad shut down during the early 1960s. Finally, the B&M elected to abandon much of the Cheshire Branch during the early 1970s.

New England was one of the earliest regions of the country to see railroads; the private Granite Railway of Massachusetts, the first of its kind ever chartered and put into operation in the United States, dates back to 1826, while the fabled Delaware & Hudson began as the Delaware & Hudson Canal Company of 1823. By the 1840s, construction was in full swing across the region. While plans had been made as early as 1829 for a railroad connecting Boston with the Connecticut River, it was not until the New Hampshire Legislature issued a charter for the Cheshire Railroad on December 17, 1844, did these hopes actually become reality. Construction of the line began in August 1845, at South Ashburnham, Massachusetts, snaking its way toward the northwest, where it reached Winchendon, Massachusetts, and Keene, New Hampshire (via Troy). Service between these towns began on May 16, 1848. Later that year, the line to Bellows Falls was completed and opened on January 8, 1849. Some years later, the Cheshire acquired a branch to Peterboro, New Hampshire, via Winchendon that had originally been built by the Monadnock Railroad, chartered in 1868.

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During these early years, there were multiple companies of various sizes operating throughout New England. For instance, the Boston & Maine and New York, New Haven & Hartford, two of the region’s best known systems, each comprised multiple smaller carriers (in the case of the New Haven, more than 200). A notable B&M predecessor was the Fitchburg Railroad, chartered in 1843 to connect Boston with Fitchburg. It eventually operated a sizeable network extending across its home state and into eastern New York. On October 1, 1890, the Cheshire Railroad was acquired by the Fitchburg, which itself was leased by the growing Boston & Maine during the summer of 1900, providing the parent a western outlet to the New York Central. From then on, the Bellows Falls line became known as B&M’s Cheshire Division, or Cheshire Branch. It saw a number of improvements under B&M ownership, such as the introduction of signaling for safer operations. In 1911, automatic semaphore signals entered service between South Ashburnham and Bellows Falls and remained in operation until the 1960s.

Over the years, the line handled a variety of freight, including textiles, milk, general agriculture, and various less-than-carloads movements (anything someone might wish to ship that would not fill an entire freight car). The western terminus of Bellows Falls also became an important interchange with the Central Vermont and, in particular, the Rutland, which depended on the B&M to carry its lucrative milk shipments to Boston. Additionally, both of the Rutland’s notable passenger trains, the “Mount Royal” and “Green Mountain Flyer,” ran sections to Boston via Bellows Falls over the Cheshire Branch. The B&M also provided its own passenger services on the line. One of the most memorable occurred during the streamlined era. In early 1935, the B&M and Maine Central launched a three-car articulated trainset, known as the “Flying Yankee,” between Bangor and Boston and manufactured by the Budd Company. The shiny, stainless-steel machine was similar to the first streamliner ever put into service a year earlier by the Chicago, Burlington & Quincy, known as the “Pioneer Zephyr” or “Zephyr 9900.”

While operated by both carriers, the trainset was a wholly-owned B&M trainset (numbered 6000) and saw several different assignments after 1940. One such routing was the “Cheshire”of 1944, operating daily between Boston and White River Junction, Vermont, via Bellows Falls. It continued serving this territory until 1952, its longest tenure over a single corridor, until it was replaced by diminutive Rail Diesel Cars (RDCs). These self-propelled rail cars were also manufactured by Budd and carried a similar, stainless-steel car body. They provided passenger service on the Cheshire Branch until 1958, when the line became a freight-only operation (the Rutland had ended all passenger trains over its system in 1953). Unfortunately, the post-war period witnessed a precipitous decline in rail service across New England while the region’s once prominent manufacturing base disappeared. Additionally, highways and airlines siphoned away other freight and passenger traffic.

When the Rutland suffered a series of strikes during the early 1960s, ultimately shutting down and liquidating the company, the B&M lost most of its interchange business at Bellows Falls. Following the B&M’s bankruptcy on February 1, 1970, it worked to shed excess and unprofitable trackage in an effort to streamline operations and improve the company’s bottom line. In doing so, it ended through-service over much of the Cheshire Branch in August 1972, while the rails remained in place for some years before finally being removed. Around the same time, a section of the line to Peterboro was abandoned north of Jaffrey, while the remaining segment was discontinued under Guilford in 1984 (this corridor now comprises the Monadnock Branch Rail-Trail).

Nearby railroad attractions in New Hampshire include several tourist railroad/excursion rides, such as the Café Layette Dinner Train in North Woodstock; Conway Scenic Railroad in Conway; Hobo Railroad/White Mountain Central Railroad in Lincoln; Mount Washington Cog Railway in Bretton Woods; and the Winnipesaukee Scenic Railroad in Meredith. Additionally, railroad museums include the Andover Historical Society in Andover; Ashland Railroad Station Museum in Ashland; Gorham Rail Station Museum in Gorham; Raymond Historical society in Raymond; and Sandown Depot Museum in Sandown.