Cumberland County was formally settled in 1798 and named for the river which runs through it, the Cumberland River. In 1829, an early settler struck oil on Renox Creek and it is generally believed to be the first gusher hit in the United States. The oil was sold as medicine in the U.S. and England under the trade name "American Oil."

During the Civil War, Cumberland County was a major natural barrier between opposing forces and so there was a great deal of fighting in the area. President Abraham Lincoln’s father, Thomas Lincoln, served two terms as constable of Cumberland County from 1802 to 1804. Additionally, two former governors of Kentucky, Thomas E. Bramlett and Preston H. Leslie, were both born in Cumberland County.

Today, Cumberland County is known throughout the Commonwealth and the entire region for its beautiful landscapes, fishing, hiking and boating activities. Every fall, Cumberland County also hosts the Cumberland River Bluegrass Festival.