The area now known as Ashland was settled in the early 18th century and inhabited prior to that by the Native Americans, to which Megunko Hill owes its name. Previously known as "Unionville", Ashland was incorporated in 1846, bearing the name of statesman 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.

Even though Ashland has left its humble roots as a rural area, it still retains the look and feel of a typical residential Boston-area New England town. Traditions like Ashland Day and small-town favorites like the ice cream shop Murphy's and breakfast joint Sunnyside Cafe maintain the feeling of a close-knit community. Ashland's longstanding rival for the Thanksgiving Day football game is Hopkinton, a rivalry with roots in the formation of the town and the resulting 1846 dispute concerning Ashland's fire engine "Megunko 1”.