Tompkinsville is a home rule-class city in and the county seat of Monroe County, Kentucky, United States. The population was 2,402 at the 2010 census, down from 2,660 in 2000. The city was named after Vice President Daniel D. Tompkins who served under President James Monroe, for whom the county was named.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. Jordan's 9th Pennsylvania Cavalry at USA garrison. Raiders captured 30 of retreating enemy and destroyed tents and stores. They took 20 wagons, 50 mules, 40 horses, sugar and coffee supplies. At Glasgow they burned supplies, then went north, raiding 16 other towns before returning to Tennessee.