[3] Archeological evidence of the farming Kichai[4] band of the Caddoan Mississippian culture dates to 200 BC in the area.

[5] The Hernando de Soto expedition of 1541 resulted in violent encounters with the Caddo Native Americans who occupied the area.

[9] Within three years of the treaty, colonization, primarily from Southern states, had been so successful that the counties surrounding Freestone had already been organized.

Continuing economic and social tensions after Reconstruction resulted in Whites lynching Blacks to keep them in place as second-class citizens.

[12] The Houston and Texas Central Railway was constructed to skirt the county to the west and south in 1870, giving the local economy a boost.

[13] and the International – Great Northern Railroad[14] The Trinity and Brazos Valley Railway,[15] laid track across the county in 1906, helping the growing economy.

The Prohibition Eighteenth Amendment to the United States Constitution took effect in 1920, banning the sale, manufacturing, and transportation of alcoholic beverages for public consumption.

In the period until its repeal by the Twenty-first Amendment to the United States Constitution in 1933,[16] some enterprising individuals in Freestone followed a national trend and began bootlegging for profit.

Freestone County is currently listed as part of the Dallas-Fort Worth DMA, although it is located in eastern Central Texas, geographically closer to the Waco metropolitan area.

Local media outlets include: KDFW-TV, KXAS-TV, WFAA-TV, KTVT-TV, KERA-TV, KTXA-TV, KDFI-TV, KDAF-TV, and KFWD-TV, and all of the Waco/Temple/Killeen market stations also provide coverage for Freestone County.

School districts include:[28] The entire county is in the service area of Navarro College, according to the Texas Education Code.