Dexter was settled beginning in 1801 by Ebenezer Small, David Smith, and others from New Hampshire, and was originally called Elkinstown. When incorporated as a town in 1816, it named itself after Judge Samuel Dexter, who was then running for governor of Massachusetts (of which Maine was still a part). The town of Brooks in nearby Waldo County was incorporated the same year and named for the opposing candidate, John Brooks. Brooks won the election. The town of Dexter, however, achieved the greater prosperity.