This part of Michigan was settled in the 1830s, after the removal of native people. Allegan County was organized in 1835, and the Plainwell area was settled soon after. It was on a stagecoach route from Kalamazoo to Grand Rapids, and later the Grand Rapids and Indiana Railroad was constructed along the same route. After the advent of the automobile, U.S. Route 131 was created and run through the town. In the 1960s, an improved 4-lane US-131 was built west of town to connect Kalamazoo and Grand Rapids, with an interchange on M-89 between Plainwell and Otsego. This allowed the town to become a kind of "bedroom community" for Kalamazoo or the southern part of Grand Rapids.