Tompkinsville is a city in and the county seat of Monroe County, Kentucky, United States. The population was 2,660 at the 2000 census. The city was named after Vice President Daniel D. Tompkins who served under President James Monroe, for whom the county was named after. Site of Confederate Gen. John Hunt Morgan's first raid of his famous First Kentucky Raid. July 9, 1862, Morgan's Raiders, coming from Tennessee on their first raid into Kentucky, attacked Major Thomas J.