Tobucky County was defined by the Canadian River, which formed its northern border, the Shawnee Hills in the west, and the San Bois Mountains in the east.
A town called Perryville was established at this strategic location in 1838, developing into a prosperous trading center and, eventually, the county seat.
On August 26, 1863, a force of 4,500 Union soldiers crossed the Canadian River and destroyed the Confederate munitions depot at Perryville.
Following the Civil War the Choctaw Nation signed a surrender treaty with the United States requiring it to allow the construction of railroads through its territory.
Constitutional officers, all of whom served for two-year terms and were elected by the voters, included the county judge, sheriff, and a ranger.
The sheriff collected taxes, monitored unlawful intrusion by intruders (usually white Americans from the United States), and conducted the census.
While this was not true of Tobucksy County, with its bustling commercial towns and profitable coal mines, it would have to be dismantled in order to accommodate changes required by the region at large.