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In a word, or rather a year, 1903. According to the Voluntaryist, that was when the first states, Missouri and Massachusetts, passed laws requiring all drivers to have a license. Up until then, horseless carriages were thought of as just that -- carriages without horses. There was no licensing requirement to "drive" a horse. Even though Missouri was first to require a driver license, it wasn't until 1952 that the state required a driver examination. Massachusetts required a driver examination for commercial chauffeurs as early as 1907. The National Conference of State Legislatures asserts that Rhode Island was the first state to require a license, passing the law in 1908.
Prior to 1903, some cities and towns tried licensing requirements. The Voluntaryist states that Chicago passed a law in 1898 requiring the owners of almost anything with wheels, including bicycles and wagons, to be licensed. That law was later ruled unconstitutional. Regulation was pretty loose in many states through the 1930s and '40s. In Georgia, for example, there was no test; one sent for a license by mail. South Dakota was the last state to pass a law requiring drivers to be licensed. In 1954, the state required drivers to be licensed, and five years later added an examination.
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