At least nineteen pioneer stations (settlements) are believed to have been established in the area during the American Revolution.

In the early 19th century, Clark County farmers began importing European livestock.

It was much larger area than present-day Bourbon County, as its original territory is now divided among Bracken, Boone, Campbell, Clark, Estill, Fleming, Floyd, Greenup, Harrison, Kenton, Mason, Montgomery, Lewis, Nicholas, Pendleton, Powell, and Robertson.

James Clark (1836–39), Jane Lampton, the mother of Mark Twain, and sculptor Joel T. Hart.

The Civil War divided the county, and about 1,000 of its men joined either the Confederate or Union forces.

The railroads helped make Winchester a transportation, commercial, and educational center, and gave rise to small service communities such as Hedges Station, six miles east of Winchester, and Ford, a once-prosperous mill town on the Kentucky River.

Hemp, which was grown to make rope, suffered from foreign competition and vanished as a cash crop around World War I.

The crop was brought back during World War II and a processing plant was built in the county.

The county remains a rich agricultural area, with farms occupying 95 percent of the land.

Clark County is the birthplace[5] of Beer Cheese, a regional delicacy that is growing in popularity across the country.

Winchester hosts the annual Beer Cheese Festival in celebration of this Kentucky original treat.

Lulbegrud Creek is named for Lorbrulgrud, the capital city of Brobdingnag, the land of giant people in Jonathan Swift's Gulliver's Travels.