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. MONROE COUNTY - TOMPKINSVILLE The only county of the 2,957 in the United States named for a President where the county seat is named for the contemporary Vice-President. County formed in 1820; named for James Monroe the fifth President, author of the Monroe Doctrine. The county seat named for Daniel Tompkins. Two terms for each covered 1817 - 1825. 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.