[3] The county was formed in 1808 and named for Captain James Estill, a Kentucky militia officer who was killed in the Battle of Little Mountain during the American Revolutionary War.

[5] Estill County has two adjacent towns, known as the twin cities, Irvine and Ravenna.

Ravenna is home to a former CSX Transportation facility, now owned by Kentucky Steam Heritage Corporation for the restoration of Chesapeake and Ohio 2716.

[6] It conducts the Ravenna Railroad Festival annually in late summer, and the historic Fitchburg & Cottage Furnaces are located here.

[8] Originally settled by European settlers entering Kentucky via old buffalo and Indian trails and traveling through Boonesborough in what is today Madison County.

[9] Estill County was one of the first areas in the United States to experience early industrialization, with iron mining and smelting beginning in 1810.

With the Red River, famous for its gorge in neighboring Powell County, forming the northern border.

Much of Estill County's development, including the towns of Irvine and Ravenna, is located in the fertile bottomlands of the Kentucky River.

Although it lies in the Bluegrass and Knobs regions, Estill County was more akin to the eastern Pennyroyal Plateau to its southwest in being strongly pro-Union during the Civil War.

[25] Consequently, Estill County has been strongly Republican ever since the end of Reconstruction – since 1888 the county has voted Democratic only for Woodrow Wilson in 1912, Franklin D. Roosevelt in 1932 and Lyndon Johnson in 1964, with the biggest of these three victories in 1932 being FDR's by a mere one hundred and eighty-seven votes out of over six thousand one hundred.