The area now known as Ashland was settled in the early 1700s and inhabited prior to that by the Megunko Indians, to which Megunko Hill owes its name. Previously known as "Unionville", Ashland was incorporated in 1846 and is considerably younger than many towns which surround it. The establishment of the Boston to Albany railroad in the mid-1800s was a key factor in the early development of Ashland. Through most of the 1800s to the mid 20th century, Ashland was a rural town with scattered farms and centralized residential buildings with some industry. Ashland is where inventor Henry E. Warren invented 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. A Warren Synchronizing Timer is on display at the Smithsonian's Museum of American History. Also of note was the construction of the Ashland Reservoir around 1900, from the waters of Cold Spring. This is the current site of Ashland State Park. Through most of the 20th century Ashland's population remained slow in growth, until the post-war boom beginning in the 1950s. Ashland grew from a far-removed rural town 22 miles west of Boston to a primarily residential suburb by the 1980s. Many farms and open spaces have given way to housing, although some untouched land still remains. This includes the Ashland Town Forest and Ashland State Park. Two major routes, 135 and 126, pass through Ashland. Route 135 is dominated by older residential development of varying density and is also part of the route for the Boston Marathon, which started in Ashland until the start was moved to Hopkinton in 1924. Route 126 has seen much more growth since the 1980s, as farms have given way to shopping centers and condos. Part of the draw of Ashland, and one that has been publicized in recent years, is its "ideal" location about halfway between Boston and Worcester. Ashland is considered part of MetroWest, which also consists of Framingham, Holliston and Hopkinton.

Since the town is famous as the birthplace of the electric clock, the Ashland High School sports teams have been coined "The Clockers."

Even though the current Ashland has grown from its beginnings as a rural area, it still retains the look and feel of a typical residential New England town in the Boston area. Traditions like the Ashland Day fair and small-town favorites like the ice cream shop Tasty Treat and breakfast joint Sunnyside help maintain the feeling of a close-knit community. Ashland's traditional rival is Hopkinton for the Thanksgiving High School football game. Ashland High School graduates approximately 160 students each year, though that number is increasing with each passing year.

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