In the early nineteenth-century, Caldwell County witnessed the passage of the forced migration of the Cherokee to the West on the Trail of Tears during Indian removal.

The Cherokee camped for several weeks in Caldwell County during the winter of 1838, mainly at Big Springs, now in downtown Princeton; at Skin Frame Creek, and in the Centerville area near Fredonia.

Strongly pro-Confederate and one of the counties that sent a secessionist delegate to the Russellville Convention, which signed an Ordinance of Secession forming the Confederate government of Kentucky.

Following the Confederate retreat in early 1862, however, Union soldiers occupied Princeton for the remainder of the war.

In December 1864, raiding Kentucky Confederate cavalry commanded by General Hylan B. Lyon burned the Caldwell County courthouse in Princeton, since it was being used to house the Union garrison.

The expansion of railroads in the late nineteenth century made Princeton an important junction on several major railway lines, most notably the Illinois Central and the Louisville & Nashville.

Under the leadership of Dr. David Amoss of Cobb in Caldwell County, a vigilante force called the Night Riders was formed to strengthen the persuasion.

The Night Riders terrorized those who cooperated with the tobacco company by destroying crops, burning warehouses, and attacking individuals.

The "Black Patch Wars" came to an end around 1908, finally suppressed with the aid of the Kentucky state militia.