[2] The county is named for Virginia statesman James Madison, who later became the fourth President of the United States.

[6] Madison County is home to Eastern Kentucky University, Berea College, and historic Boone Tavern.

[7] Famous pioneer Daniel Boone lived in Madison County and built Fort Boonesborough, now a state historic site.

Indian trader John Findley, Daniel Boone, and four others first came into the area that is now Madison County in 1769 on a hunting and exploring expedition.

In 1774, the Transylvania Company, led by Judge Richard Henderson of North Carolina, purchased 20,000,000 acres (8,100,000 ha) of land west of the Appalachians (including present-day Madison County) from the Cherokee Nation.

Daniel Boone was hired to cut a trail through the Cumberland Gap and establish a settlement on the Kentucky River.

Both the relatively large 18-to-24 population and the relatively low median age can be explained by the presence of Eastern Kentucky University, and to a considerably lesser extent Berea College.