Tompkinsville is a home rule-class city in and the county seat of Monroe County, Kentucky, United States. The population was 2,309 at the 2020 census. The city was named after Vice President Daniel D. Tompkins who served under President James Monroe, for whom the county was named.

Monroe County is a county located in the Eastern Pennyroyal Plateau region of the U.S. state of Kentucky. Its county seat is Tompkinsville. The county is named for President James Monroe. It was a prohibition or dry county until November 7, 2023, when voters approved the sale of alcohol.