Hartsville, the seat of justice and the county's only town, began in 1797 as Donoho's Mill. Charles and Sarah (Brooks) Donoho, and James and Sarah (Hamilton) Hart, and their children, were among the settlers at this place in 1797, the Donoho's on the east side of West Fork of Goose Creek, the Hart on the west side on the same stream. The Donoho's operated the mill, and nearby on the Cumberland River the Harts, in 1798, opened a ferry, known for well over a half a century as Hart's Ferry. In 1800, Charles Donoho sold his mill to James Hart. Within a few years after 1797, Harts Race Track, for racing became noted. This, plus the opening of the post office in 1807, along with Andrew Allison's and George Black's store, put Hartsville on the map indefinitely. In 1817, the State Legislature officially declared Hartsville an established Tennessee town. Damascus, a name given to the Donoho side of the creek, lost currency when both sides of Goose Creek were merged in 1840 under one incorporation, this by legislative act. James Hart who died as postmaster and esquire, and on whose land the town was originally laid out, is today known as the Founder of Hartsville, Tennessee.
Wirt Seminary, later known as Wirt College, and still later as Enon College, was a rather energetic and well known institution from its beginning in early 1838 until its final closing about 1881. Its campus was located six miles west of Hartsville near the present Payne's Store. More permanent, however, was the Hartsville Masonic Institute, which originated about 1838 in the Central Female Academy. The Masonic Order obtained their ownership in 1868 and by September 1875, the Institute had absorbed the nearby Hartsville Masonic Institute Male Academy which had absorbed itself established about January, 1837. The Hartsville Masonic Institute continued in operation, with a widespread clientele, as a private academy until 1910 when it became a publicly owned institution under the name Hartsville Academy. The old school provided a firm foundation for the present Trousdale County High School which succeeded it in 1916 and which itself occupied the old institute building through December 1919.
The county seat has had its share of fires. Courthouses were lost in the fires of 1900 and 1904. County records were destroyed in 1874, 1900, and 1905 and few records predate 1906. Other fires occurred in 1877 and 1902. Floods have hit every decade or so, also, the most notable being December 1927. Locals refer to such floods as "the back water".
In March 1883, the telephone reached the old Upper Cumberland of Tennessee, and the Hartsville area in particular, and life has never been as quiet since, nor events very far away.
The railroad came to Trousdale County in 1892, eventually replacing the river as the major cargo-way, and cementing and strengthening the county's position as a major tobacco trade center, for which it has been primarily known, until just recently.
The county's most successful annual event has been the Tobacco Bowl Football Classic, a post-World War II development. Other sports are enjoyed as well.
The county probably has a greater percentage of paved roads than any other county in Tennessee. Trousdale saw its first traffic light go up in 1946, it's first parking meters in 1952, it's first rest home in 1956, and by 1960, it had six punch-clock-type factories. Between 1880 and 1970, Trousdale's population averaged between five and six thousand, with little variation. The county went Republican for the first time in 1972.
Trousdale County is the smallest county in the state with 75,000 acres.