Pleasant Hill met a fate common to towns near the Missouri-Kansas border: occupation by armies on both sides of the war and the gradual destruction of many of the town's buildings.
Early in the war, the town of Dayton, Missouri gained a reputation as an enclave for Southern sympathizers and a fertile recruiting area for the secessionist Missouri State Guard.
After hearing of Missouri State Guard recruitment activities in Dayton, Missouri, Union Colonel Charles R. Jennison sends the Seventh Kansas Cavalry to the town.