It is today part of the Old Mulkey Meetinghouse State Historic Site.

During the Civil War, Tompkinsville was the site of Confederate General John Hunt Morgan's first Kentucky raid.

On July 9, 1862, Morgan's Raiders, coming from Tennessee, attacked Major Thomas J. Jordan's 9th Pennsylvania Cavalry.

Raiders captured 30 retreating Union soldiers and destroyed tents and stores.

At Glasgow, Kentucky, they burned supplies, then went north, raiding 16 other towns before returning to Tennessee.

Tompkinsville is home to the famous Dovie's restaurant which has been known for its signature deep-fried hamburgers since 1938.

[5] Alcohol sales became legal in the city, along with Monroe County as a whole, in 2023 after a referendum.

37.8% of all households were made up of individuals, and 18.4% had someone living alone who was 65 years of age or older.