Originally called Watson's Crossroad, Olive Branch was founded near where several old Chickasaw Indian Trails crossed.  When the first post office was established in 1846, Mrs. Frances Wilson Blocker - a descendant of one of the community's founders - suggested the name Olive Branch.  She felt the new name symbolized a dove bringing a branch to the seagoing Noah.  On May 1, 1874, Olive Branch was incorporated as a town and on March 6, 1888, it progressed to Vilage Status.

Among the earliest settlers in the Olive Branch area where Stephen Flinn and his wife's brother-in-law, Milton Blocker.  They purchased DeSoto County Sections 34 and 35 from Chickasaw Chief Lush-pum-tubby for $1,600.  Blocker was probably responsible for the village's first business, a mule-powered cotton gin.  Later, a creamery and boat factory boosted the community's economy, an indication of what was to come.

Emphasis on education began as early as 1836 with the establishment of the Rock Springs School located in a log cabin near the Pleasant Hill community. In 1911, DeSoto County Agricultural High School was established on land donated by Milton Blocker, Jr. and his daughters.

At the dawn of the 20th century, Olive Branch began to emerge as a commercial center as well as an agricultural one, eventually eclipsing the thriving settlements of Pleasant Hill and Cockrum.