The Mississippi state legislature created Chickasaw County on February 9, 1836. It was named for the Chickasaw Indian Tribe that occupied the northern part of Mississippi.  The county, when organized was much larger than it is now, included most of what is now Calhoun County, the northern part of Clay County and the extreme northeastern part of Webster County.  Chickasaw County originally contained 1,077 square miles of territory but now only encompasses about 507 square miles.

The Natchez Trace Parkway goes through the middle of Chickasaw County.  The county is also host to the southern terminus of the Tanglefoot Trail, the longest Rails to Trails cycling byway in Mississippi.  There’s camping, hiking, horseback riding, hunting, fishing, and miles of off-road ATV trails in Chickasaw County. Add to that short travel times to the commercial center of Tupelo, Ole Miss and Mississippi State, and you will find Chickasaw County is a fine base from which to explore the region and get a taste of that real Mississippi that Bobby Gentry sang about.

Chickasaw County is the home to four towns, each with significant historical factors.  Houlka is Chickasaw County’s oldest town, originally an Indian village.  Houston was organized in 1837 as the county seat and named in honor of Sam Houston, a friend of Joel Pinson.  Pinson donated the land for the town on condition that it be named after his childhood friend.  In 1877, the legislature enacted a law dividing the county into two judicial districts with Houston as First and Okolona as Second.  Okolona was initially established in 1845 and incorporated in 1850.  It soon became the dominant economic center of Chickasaw County because the railroad passed through town.  Woodland was established sometime between 1900 and 1906 just south of Houston.