For more than a thousand years and into the 1800s, the northern one-third of what is now Mississippi was the exclusive domain of the Chickasaw Indians who, according to legend, migrated to this area from the northern Pacific coastal region. Modern linguists confirm there are striking similarities in the Chickasaw language and that of some west coast tribes in the Oregon area, giving credibility to the legend.

The first Europeans to explore the southeastern part of the future United States were the Spaniards under Hernando DeSoto in 1540/42. The natives he encountered were a people in transition from the original Mound Builders to the Indian tribes that would emerge later. After pillaging the area for several years, DeSoto discovered the Mississippi River in May of 1541 at a point most historians believe to be near the present day town of Walls, Mississippi. We know he approached the River from the east so his route most likely carried him through the Olive Branch area several days earlier, making him the first European to set foot here.

In the early nineteenth century, with the new United States growing rapidly and spreading westward as Territories became States, the Indian situation in The Mississippi Territory was a major concern of President Andrew Jackson and the government in Washington. The government was unable to keep settlers off Indian lands and the Indians were having a difficult time living under Territorial and State laws. With the situation becoming critical, President Jackson sent a delegation under General John Coffee to negotiate a treaty with the Chickasaws. As a result of the Treaty of Pontotoc Creek forced upon the Chickasaw Nation by the United States in 1832, the Chickasaws were required to sell their land in North Mississippi and relocate to a land grant in the Oklahoma Territory, thereby opening up all of Mississippi to settlement. Twelve new counties (including DeSoto) were created in North Mississippi from the land obtained from the Chickasaw Nation and the floodgates were opened for settlement.

The first settlers to arrive in this area in March of 1836 were Milton Blocker and Stephen Flinn and their families. Blocker and Flinn were brothers-in-law by reason of their being married to the Wilson sisters, Frances and Amorando. They had left their farms in Limestone County, Alabama, loaded their belongings on a flatboat and floated down the Tennessee River, the Ohio River and the Mississippi River to Memphis where they disembarked. They loaded into wagons and headed southeast into the newly opened Chickasaw Territory. They had not traveled far when they chanced to meet a Chickasaw Indian Chief named Lush-Pun-Tubby who had been given two sections of land (1,280 acres) under the provisions of the Treaty of Pontotoc Creek. On April 13, 1836, they negotiated the purchase of the 1,280 acres (Sections 34 and 35) from Chief Lush-Pun-Tubby for $1.25 per acre. We do not know what happened to Lush-Pun Tubby after that; he probably followed his people to the Oklahoma Territory and lived out his days there. We do know that new settlers were flooding into the new area where Blocker and Flinn had settled and a community began to develop where present day Olive Branch is located.

Milton Blocker built the first house in the new community on a site in the general area of present day Shady Grove Cove. He then built a sawmill on a hill several hundred yards west of his house where Blocker Cemetery is presently located. The sawmill produced lumber for the settlers now streaming into the new community. In 1840 Blocker would buy out Flinn's interest in most of the 1,280 acres and earn his place in history as the father of Olive Branch. Blocker would be killed seven years later in 1847 on a trip down the Mississippi River to New Orleans when the boiler of the steamboat, Medora exploded and the boat sank. Both Blocker and Flinn are buried in Blocker Cemetery.

The thriving new community just happened to be located at the half-way point of a two day trip along Pigeon Roost Road from the agricultural community that was developing around Holly Springs to the markets in Memphis. In the early 1840s, some enterprising individual built some pens alongside Pigeon Roost Road to overnight the livestock on their trip to market and the town, ignominiously, became known as Cowpens. That name, obviously, did not set well with the residents of the community and in 1842, the town was renamed Watson's Crossroads in honor of the Methodist minister, Sam Watson.

In 1846, the town received its first Post Office and the church ladies renamed the community Olive Branch in reference to the Biblical story of Noah and the flood, and it has been that ever since. It is said that Milton Blocker's wife, Frances actually came up with the name.

Olive Branch managed to escape the ravages of the Civil War with only several minor skirmishes taking place southwest of the town in the Pleasant Hill area. The first engagement, on September 8, 1862 involved Colonel Ben Grierson's Federal cavalry routing a band of Confederate irregulars. In the other action, on April 9, 1863, Confederate General Richard Taylor defeated Union General Banks in a minor battle involving a limited number of troops.

In 1874, Olive Branch was incorporated and elected its' first Mayor, Ben Wesson. Wesson served only one term as Mayor until 1877. He would later serve as Postmaster from 1880 until 1888. In 1875, while Mayor, Wesson built his home on property at the junction of Pigeon Roost Road and Pleasant Hill Road (now Goodman Road). Today it is known as The Wesson House and is a Dedicated Mississippi Landmark, one of only three in DeSoto County.

In 1885, the Memphis to Birmingham Railroad was built through Olive Branch creating a commerce junction and setting the town apart from the other small farming communities in the area.

For the next three-quarters of a century, Olive Branch's growth was uneventful, not unlike most other small Mississippi townships. Her sons fought and won two world wars. Her citizens endured the great depression and managed to pave her streets, electrify her homes and businesses, build sewer and utility systems, establish schools, police and fire departments and evolve from being a rural agricultural community to becoming a modern dynamic city poised to take advantage of the tremendous growth that would take place in the last quarter of the century. During the first three-quarters of the twentieth century, the population grew from several hundred to several thousand.

In 1969, Holiday Inns of America purchased 3,000 acres of land to the east of Olive Branch to develop an industrial park, an airport and a training facility for its' hotel managers. The training facility was known as Holiday University (now Whispering Woods Hotel). The development of that complex along with the opening of Interstate Highway 78 in 1974, set the stage for the phenomenal growth that took place in Olive Branch in the last quarter of the twentieth century. The population growth between the 1990 and the 2000 census exploded from 3,750 to over 21,000 making Olive Branch the fastest growing city in the nation with a growth rate of nearly 600% for the decade.

Olive Branch, because of its' natural proximity to Memphis, its' unequaled residential areas protected from commercial encroachment by progressive zoning and control ordinances established by responsible government, its' excellent school system, its' recreational opportunities provided by one of the largest municipal parks in the State and five tournament-quality golf courses, its' exemplary public safety organizations, its' employment opportunities provided by a diverse, recession-proof manufacturing and distribution Industrial Park, the State's second busiest airport, its' commitment to balance the burgeoning commercial growth with the preservation of the historical heritage of the City and its' small town atmosphere as exemplified by Olive Branch Old Towne, its' high property value retention coupled with a reasonable cost-of-living and the genuine friendliness of its' people will continue to make Olive Branch one of the nation's most desirable residential communities for decades to come.