Hopkinsville was settled in 1796 by Bartholomew and Martha Ann Wood, a couple from Jonesborough, Tennessee. The Wood family established a permanent settlement in the vicinity of present-day West Seventh and Bethel Streets, near what would become known as the Old Rock Spring. Wood staked a claim, based on his service in the Revolutionary War, on 1,200 acres of land. He built a second cabin on what is now the northeast corner of Ninth and Virginia streets and a few years later built a home southeast of Fourteenth and Campbell streets, where he died in 1827. Wood's settlement soon attracted other settlers, and a pioneer village emerged.
Wood donated five acres of land and a half interest in his spring for the county seat. The following year a log courthouse, jail, and 'stray pen' were built on the public square facing Main Street. The plat for the town, first called Christian Court House, was surveyed by John Campbell and Samuel Means in 1799. In honor of Wood's eldest daughter, the town was renamed Elizabeth that same year. However, a town in Hardin County had the same name, and when the city incorporated in 1804, the General Assembly renamed the settlement Hopkinsville, in honor of General Samuel Hopkins of Henderson County.
The Civil War generated major social and economic division among the people in Hopkinsville and Christian County. A physical evidence of this discord led to the establishment of Union Camp Joe Anderson, located northwest of Hopkinsville. Men who trained there became members of the 35th Kentucky Cavalry, the 25th Kentucky Infantry, and the 35th Kentucky Mounted Infantry. Union General James S. Jackson, a Hopkinsville attorney before the war, was killed in the Battle of Perryville, Kentucky, in October 1862. Private citizens who supported the Union cause provided the army with mules, wagons, clothing, and food. Confederate support in Hopkinsville and Christian County was evident in the establishment of the Oak Grove Rangers and the 28th Kentucky Cavalry.
Christian County was the birthsite of Jefferson Davis, President of the Confederate States of America. Several local businessmen and plantation owners contributed money and war supplies to the 'Lost Cause.' The war period brought military take-over of Hopkinsville at least half a dozen times by both Confederate and Union forces. In December 1864, Confederate troops under General Hylan B. Lyon captured the town and burned the Christian County courthouse. A skirmish between Union and Confederate forces took place in the field across from Western State Hospital near the end of the war.
In the early years of the twentieth century, tobacco planters formed a protectionist Dark Tobacco District Planters' Protective Association of Kentucky and Tennessee. This was in opposition to a corporate monopoly: the American Tobacco Company (ATC) trust, owned by James B. Duke.
Many farmers found that they could no longer sell their tobacco crop at a profit and that the ATC was the region's only buyer, now that the many tobacco companies had formed the trust using that agency to purchase all tobacco from any farmer at a fixed price. Upon establishing the protective association and rivalling the monopoly by practicing boycotts of tobacco sales, some farmers formed the Silent Brigade in an effort to apply social pressure for the purpose of terrorizing farmers into joining the Association against the Trust and holding to its boycott of raising no tobacco or selling no tobacco.
The Silent Brigade was later to be infamous as the Night Riders, assembled and regulated by suspected leader Dr. David A. Amoss. The Night Riders, as they were called, were sometimes regarded as heroes by farmers whom they helped although they were often known for violence by some members within their ranks and their organized fight against the changing tobacco industry .
On December 7, 1907, 250 masked night riders captured police and sheriff posts and cut off the town from outside contact. They then pursued city officials and tobacco executives who were buying cheap tobacco from farmers who were not members of the Dark Tobacco District Planters' Protective Association. Three warehouses were burned during a night of lawlessness. Peace Park in Hopkinsville was created on the site of one of the warehouses and is now one of the towns major visitor attractions.