Incorporated in 1794, Greensburg, the county seat of Green County, began as Glover's Station, a wilderness settlement in the Kentucky Territory on the Cumberland Trace, an offshoot of the Wilderness Road. From 1800 to 1840, Greensburg flourished as a center of trade and learning. At this time, Greensburg had fine cabinet makers, silversmiths, rifle makers, cigar factories, and distilleries. Hundreds of locally built flatboats, loaded with hogsheads of tobacco and other local products, floated from Greensburg down the Green River to New Orleans. Green County, formed in 1792 as the thirteenth county in the Commonwealth, had its boundaries diminished to provide land for part or all of eight other counties.
The city and county boast many Abraham Lincoln and Civil War connections: Mary Owens, one of Lincoln's first loves; William Herndon, Lincoln's law partner; Lincoln's appointee as U.S. Consul to Mexico in 1863, Reuben Creel; Mentor Graham, who after moving to Illinois became an educator of Lincoln; and Union generals, E.H. Hobson and William Ward. Other famous citizens include Father David Rice, an early Presbyterian minister, and Jane Todd Crawford, who rode on horseback to Danville where Dr. Ephraim McDowell successfully performed the world's first successful ovariotomy on her on Christmas, 1809.
The Greensburg National Register Historic District is composed of 47 contributing properties, covers 15 acres, and includes "the Oldest Courthouse West of the Alleghenies" (1804), The Woodson Lewis Building (1900) and the Old Depot (1913).