Harrodsburg was the first city formally chartered in Kentucky County, the Virginia district that later became the 15th state.

Pleasant Hill, also known as Shakertown, is the site of a former Shaker community, active especially in the years before the American Civil War.

The 19th Kentucky Infantry (Union) was organized at Camp Harwood for a three-year enlistment commencing January 2, 1862, commanded Col. William J. Landram.

The remainder of the regiment was organized in Louisville, Kentucky, and mustered in for three years on September 26, 1862, under the Colonel Alexander W. Holeman.

Following the Battle of Perryville, much of Harrodsburg and surrounding towns were converted into makeshift hospitals; 1600 sick and wounded Confederate soldiers were captured during a raid in Harrodsburg by the 9th Kentucky Cavalry on October 10, 1862.

The rail yard and station were located at the corner of Office Street and Merimon Avenue.

A spur was later constructed from the station to Burgin, where the Louisville Southern joined the Cincinnati Southern's Cincinnati, New Orleans and Texas Pacific Railway CNO&TP mainline which runs through the eastern part of the country from High Bridge of Kentucky to Burgin to Danville was opened in 1877.

Company D of the 192nd Tank Battalion, which took part in the World War II Battle of Bataan was from Harrodsburg.