The Norwottuck Rail-Trail comprises two different sections of rights-of-way originally owned by two railroads. The segment east of Northampton (known as the Mass Central Section) is roughly 10 miles, and for many years was owned by the Boston & Maine. It was originally built, however, by a predecessor during the late 19th century. The other segment runs west of Northampton (known as the Francis P. Ryan Section) and follows about 5 miles of a former New York, New Haven & Hartford branch. Neither corridor saw particularly heavy use (passenger service on both ended particularly early), and each was abandoned between the 1930s and 1970s.

The western Francis P. Ryan Section of the trail was the first to be completed. This corridor had a long history well before the line ever reached the Northampton area. It began as the New Haven & Northampton (NH&N), a railroad chartered in 1846 to build north of New Haven, Connecticut, next to the Farmington Canal. As a result, it gained the moniker “Canal Line.” Most of this former NH&N right-of-way across the state is today’s Farmington Canal Heritage Trail. In 1848, the NH&N opened its first section between New Haven and Plainville. It continued pushing north over the next 20 years and reached Northampton, Massachusetts, by 1858. Later it extended to Shelburne Falls and Turners Falls. There were a handful of other notable branches radiating from the main line, serving Westfield (via Holyoke), New Hartford (via Farmington), and Williamsburg (via Northampton). The Francis P. Ryan Section follows about 5 miles of the latter, first opened for rail traffic on February 1, 1868.

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On May 14, 1887, the growing New York, New Haven & Hartford formally leased the NH&N, which became known as its Northampton Division and was later referred to as the Air-Line-Northampton Division. The New Haven became one of southern New England’s most important systems for its high-speed, partially electrified route between Boston and New York (the famed “Shore Line”). It became a necessary means of travel for commuters, and during the region’s industrial years, moved a wide variety of freight as well.

Through the early 20th century, such was the case with the Northampton line, which also offered an interchange point at Northampton with the Boston & Maine. However, traffic drifted away considerably after World War II, and the New Haven found itself in an increasingly precarious financial position into the 1960s. Following its 1961, bankruptcy the company began abandoning its Williamsburg Branch, first from Williamsburg to Florence in 1962 and the rest of the line between Northampton and Florence in 1969, when New Haven was included in the Penn Central merger. Today, almost nothing remains of the entire Northampton Division.

The Mass Central Section of the Norwottuck Rail-Trail was once part of the Boston & Maine. Its history begins as the Wayland & Sudbury Railroad, incorporated in 1868 by the state legislature to build from Stony Brook near Boston (and a connection with the Fitchburg Railroad) to Sudbury. In May 1869, it was renamed as the Massachusetts Central Railroad, and the company had ambitious plans to push the line west across the state from Boston to Northampton, perhaps even to the Hudson River (which it never reached). Unfortunately, from the start it was beset with issues ranging from natural disasters to financial problems. As a result, construction was slow. In 1881, Boston and Hudson were linked, a distance of 28 miles, opening October 1 that year. By 1882, westward expansion had reached Jefferson (48 miles), although bankruptcy befell the company in 1883; it was reorganized later that year as the Central Massachusetts Railroad (CMRR).

In December 1886, the property was leased to the Boston & Lowell Railroad (B&L) with the stipulation that the route to Northampton be completed. Four months later, the B&L itself was leased to the growing Boston & Maine (which formally took control during 1901), but construction nevertheless proceeded quickly and was completed by December that same year. For a brief time, the CMRR was B&M’s primarily link to the west until the latter leased the Fitchburg Railroad in 1900. This new Fitchburg Division operated a more efficient, northerly route across the state, connecting Boston with Greenfield via Fitchburg.

For some time during the early 20th century, however, the former CMRR property did well under the B&M banner, seeing strong patronage and dozens of through-trains daily. Business remained this way through the 1920s, but the Great Depression hit the line hard. Automobiles and trucks also took away both freight and passenger traffic. In 1932, the last passenger through-train left Boston for Northampton and it seems even Mother Nature wanted rid of the line. The 1938 New England Hurricane severely damaged central portions of the route, leading to its abandonment in 1939 between Hardwick and West Boylston. This left two large eastern and western branches. The former survived for commuter service but was slowly cut back starting in the 1950s; it had largely been removed by the early 1970s. The latter became known as the Wheelwright Branch and suffered the same fate; large sections were abandoned by the 1970s, including what is now the Mass Central Section of the Norwottuck Rail-Trail.

Railroad attractions across the state of Massachusetts include the Berkshire Scenic Railway in Lenox; Cape Cod Central Railroad in Hyannis; Chatham Railroad Museum in Chatham; Edaville USA attraction and train rides in South Carver; Old Colony & Fall River Railroad Museum in Fall River; Shelburne Falls Trolley Museum in Shelburne Falls; and the Walker Transportation Collection and Beverly Historical Society & Museum in Beverly.