Upon the creation of Breathitt County in 1839, local landowner Simon Cockrell Sr. donated 10 acres (4.0 ha) to serve as its seat of government.

[6][7] Local feuds led the national press to publish stories about Jackson and "Bloody Breathitt": state troops were dispatched twice in the 1870s and again in 1903 – after the assassination of U.S. Commissioner James B. Marcum on the courthouse steps[8] – to restore order.

[7] The Kentucky Union Railroad reached the city in 1891, and Jackson boomed until the L&N continued the line on to Hazard in 1912.

[4] The climate in this area is characterized by relatively moderate temperatures and evenly distributed precipitation throughout the year.

The Köppen climate classification places the city in the humid subtropical zone, which is abbreviated as Cfa.

In addition, although the area falls under USDA hardiness zone 6b,[11] the record longest streak without 0 °F (−18 °C) lows occurred from February 6, 1996, to January 15, 2009 (12 years, 344 days).