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The electric trolley was first introduced to Western Massachusetts in Springfield in 1889, and over the next decade trolley systems spread to the larger towns of the region. Starting around 1902, some regional networks were built in New England, particularly in the Boston area. By 1907, it was possible to take a trolley from Springfield to Worcester and on to Boston using different companies' lines. In Greenfield, the Electric Street Railway Company began operation in June, 1895, with runs to Turners Falls and Millers Falls. Neighboring communities built their own rail lines, and by 1905 Greenfield was linked by trolley to Northampton, Amherst, and Montague and points in between. These companies consolidated that year into the Connecticut Valley Street Railway. By 1910, a well developed network of electric trolleys meant that a passenger could ride from Greenfield to Boston, New York, or Philadelphia. Trolley links connected cities all the way to Chicago, paralleling the existing steam lines. But the rise of the automobile and labor costs meant that the street railways began to decline after World War I. The Connecticut Valley Street Railway went into bankruptcy in 1923. The system in and around Greenfield was purchased by the town in 1924, which resuscitated it; however, the system collapsed during the Great Depression.

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