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The area now known as Ashland was settled in the early 18th century and inhabited prior to that by the Megunko Native Americans, to which Megunko Hill owes its name. Previously known as “Unionville”, Ashland was incorporated in 1846, bearing the name of statesman Henry Clay’s Kentucky estate. It is considerably younger than many of the surrounding towns, as Ashland’s territory was taken in near-equal parts from the previously established towns of Hopkinton, Holliston (previously of colonial era Sherborn’s territory), and Framingham.

The construction of the Boston & Worcester Railroad, later the Boston & Albany, in the 1830s was key to the early development of the town. Decades later, two other rail lines opened stations in Ashland. Along with the Sudbury River, the railroad helped to attract numerous mills to develop a bustling boot and shoe industry. However, by constructing three reservoirs along the river in 1878, the Boston Water Board inadvertently stymied further growth, most notably by halting the construction of the Dwight Printing Company’s granite mills. Although the mills closed, starting in the 1890s the Hopkinton Railroad Company, providing a connection to Milford, and the Natick Street Railway, which operated streetcars between the towns of Sherborn, Framingham, and Natick, offered service in Ashland. These rail lines were gone by the 1920s, rendered obsolete by automobiles.

Around the same time that the local rail lines were in decline, the inventor Henry E. Warren developed the Warren Synchronizing Timer in 1916, which made synchronous electric clocks possible by keeping alternating current flowing from power plants at a consistent sixty cycles per second. Warren founded Telechron, which, in partnership with General Electric, manufactured electric clocks in Ashland until 1979, thirteen years before Telechron itself became defunct. A Warren Synchronizing Timer is on display at the Smithsonian’s Museum of American History in Washington D.C., and the Ashland High School sports teams are called “The Clockers”.