- Founded (1844)
- Raided by Daniel R. Anthony (January 1861)
- Battle of the Ravines, nearby (July 11, 1862)
- General Order No. 11 (August 25, 1863)
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. Quantrill's Raiders skirmished with Union soldiers on several occasions, including the "Battle of the Ravines" on July 11, 1862. After Quantrill's infamous raid on Lawrence in 1863, General Thomas E. Ewing issued General Order No. 11, which depopulated the rural areas of four western Missouri counties, including Cass County, the location of Pleasant Hill. Although residents of Pleasant Hill were not forcibly removed, the town at war's end resembled the nickname of the rest of the area after Order No. 11, "The Burnt District." Today, visitors to Pleasant Hill can see the old Henley Home, which was a private residence used as an area Union headquarters during Order No. 11.