Skip to main content
HomeHistory of Okolona

History of Okolona

The Okolona Historic District is locally significant for what it represents about the historical development of Okolona as a center of commerce for Chickasaw County, and for its architecture, as a locally significant collection of 19th and early 20th century buildings, particularly notable for the variety of its historic churches and public buildings.

The period of significance spans a century, from circa 1850, when the earliest surviving buildings were constructed, to 1950, which marked the beginnings of economic changes in the area in the aftermath of the Second World War. The buildings in the district illustrate the commercial and residential development of Okolona as a center for the transportation of cotton to market, as a commercial center serving the local rural area, and as a center of government as the seat of the Eastern District of Chickasaw County. (The other county seat is located in Houston.)

The Mobile and Ohio Railroad

In the year 1848, John J. McRae, later to be Governor, came to the county as agent for the Mobile and Ohio Railroad. The company wantd to build a railroad line somewhere west of the Tombigbee River. The citizens of Chickasaw County subscribed and paid by taxation for assistance in building the railroad. The tracks were completed to Okolona and beyond in 1859. The railroad quickly became the driving factor in commerce. The economy of the community rested largely on ginning cotton and moving the ginned cotton off to market.

Early commercial development occurred on the Main Street axis perpendicular to the railroad; however, all commercial buildings from this period, and the original depot, were burned during the Civil War. https://www.msrailroads.com/Towns/Okolona.htm

Civil War


Okolona was just coming into its own when the Civil War began. Because of the railroad, the town was strategically important. As a result, skirmishes between Union and Confederate forces occurred at or near Okolona at least five times, beginning in November, 1862. In February, 1864, Federal forces under Brigadier General William Sooy Smith entered Okolona during his move from Memphis in cooperation with Major General William T. Sherman's Meridian Expedition. 

On February 22, Smith's forces, retreating from West Point, were defeated by Confederate cavalry under Major General Nathan Bedford Forrest north and west of town. In a running battle which culminated in the action at Ivey's Hill, believed to be approximately ten miles north of Okolona on the Pontotoc Road, the Federals were pushed back to Memphis. During the afternoon of the 22nd, general Forrest's younger brother Jeffrey, in command of a cavalry brigade, was killed. A number of houses and public buildings in Okolona were subsequently used as hospital sites. Hospitals were established at Okolona at other times during the war, most notably as a result of the battles of Shiloh and Corinth.


Battle of Okolona

BATTLE OF OKOLONA: Excerpts from Edwin C. Bearss, one of the most respected Civil War scholars today. He is the author of ten books and over one hundred articles. Among his many works are "The Battle At Wilson's Creek', "Forrest At Brice's Cross Roads", and the soon to be published two volume epic "The Vicksburg Campaign". He is the recipient of the Department of the Interior's Distinguished Service Award, the highest award given by the department. This article may be read on the portrait, "Southern Steel".

In early February 1864 Maj. Gen. William T. Sherman marched 20,000 soldiers eastward from Vicksburg to Meridian, Mississippi, driving Lt. Gen. Leonidias Polk's little army into Alabama. Sherman's army remained at Meridian from the 14th to the 20th anxiously awaiting the arrival from Memphis of 7,000 cavalry led by Maj. Gen. W. Sooy Smith. Not hearing anything from Smith, Sherman led his columns back to Vicksburg. Sooy Smith and his powerful mounted corps on their foray deep into Mississippi were fated to meet Maj. Gen. Nathan Bedford Forrest and his 2,500 "critter" cavalrymen. Although the Yanks outnumbered the Rebs almost three to one, Forrest, one of the great combat leaders of American history, evened the odds. Forrest, a physically powerful man, knew that war meant fighting and fighting meant killing: a philosophy that made him a terrible enemy. In the running engagement, knows as the battle of Okolona, Forrest demonstrated these qualities of leadership as he and his men put the "skeer on Sooy Smith and his corps."

Smith's 7,000 horsemen had left Memphis on February 11, ten days late. When they took the field, their march was slowed by muddy roads, and it was the 116th before they crossed the Tallahatchee at New Albany. Riding down the Pontotoc Ridge, the bluecoats struck the Mobile & Ohio Railroad at Okolona on February 18. Two days later, one mile north of West Point, Sooy Smith's troops encountered and drove one of Forrest's brigades through the town. Smith now lost his nerve. Satisfied that Sherman was already en route back to Vicksburg from Meridian and that Forrest had been reinforced, Smith, on the 21st, retired from West Point to Okolona.

Forrest and his men resumed the pursuit at first light on the 22nd. By mid-morning the Confederates had advanced some 14 miles overtaking the Yankees as they neared Okolona. Forrest's efforts to cut off and destroy the enemy rear guard as it passed through the town were frustrated by the usual problems in coordinating converging columns, and the enemy retreated northwestward up the Pontotoc road. The chase continued, Forrest leading his escort.

At Ivey's Hill, some six miles beyond Okolona, the Federals came to a stand. Dismounting they occupied a timber-covered ridge and threw up fence rail barricades across the road. Col. Jeffrey Forrest, the general's youngest and favorite brother, led the attack on the Yankee roadblock. In the ensuing desperate fighting, Jeffrey was shot through the neck and fell mortally wounded, within 300 yards of the enemy strongpoint. His men faltered as they saw their leader fall, and, dismounting, they prepared to hold the ground gained. General Forrest informed that his brother had been shot, galloped to the site and dismounted. Jeffrey died as Nathan Bedford cradled him in his arms and called out "Jeffrey, Jeffrey" in a voice choked with emotion. Satisfied that Jeffrey was dead, Forrest kissed him on the forehead, laid him down, and called for Maj. John P. Strange, and, with tears in his eyes, asked him to take care of his brother's body.

In the immediate vicinity, battle-hardened Confederates had ceased fire, but to the right and left the dismounted Rebels exchanged shots with the bluecoats on the ridge. As Reinforcements came into view, Forrest remounted and brandishing his saber ordered his bugler to sound the charge, as he shouted for his men to follow him. With his escort hard on his horse's heels, Forrest galloped toward the enemy, and to some of his people his actions seemed "so rash as to savor madness." The Federal troopers defending the roadblock "broke to the rear and retreated at great speed." Forrest, closely trailed by some 120 of his men, pursued. About a mile up the road, some 500 Yanks were encountered. Forrest, undaunted by the odds, assailed the roadblock. One of the war's most furious hand-to-hand fights occurred. In which the general killed three of the enemy horse soldiers. Just as it seemed that Forrest and his small force was about to be overwhelmed, Col. "Black Bob" MuCullough, wounded earlier in the day's fighting, led his brigade to his general's rescue, brandishing his bloodstained bandages above his head as a flag.

The Federals gave way before the Rebel reinforcements, pulled back about a mile, and rallied on a plantation house, its outbuildings, and fences. Forrest's horse, as he led his men toward the stronghold, was killed. One of the escorts surrendered his steed to the general, as the Federals soon abandoned this position in favor of another roadblock, while General Smith and their officers sought to buy time. Here there was another short, sharp fight, in which Forrest's second horse was shot down. His favorite charger "King Philip" was brought up, and Forrest rode him until nightfall, closing the day's fighting, though "King Philip" received a light neck wound.

The day's last battle took place halfway between Okolona and Pontotoc, when the Yanks "made a last and final effort to check pursuit." There were charges and countercharges before the Federals disengaged abandoning a cannon. Dusk was at hand and Forrest, seeing that his men and his mounts were fagged out by two days of marching and fighting which had brought them nearly 50 miles-from the crossing of the Sakatonchee to within ten miles of Pontotoc-called a halt.

Discouraged and beaten, Sooy Smith's once proud corps hurried on to Memphis, where they arrived on February 27. A Union brigade commander best summed up Forrest's accomplishments: The retreat to Memphis was a weary, disheartening, and almost panic-stricken flight, in the greatest disorder and confusion, and through a most difficult country. The first Brigade reached its camping-ground five days after the engagement, with the loss of all its heart and spirit, and nearly fifteen hundred fine cavalry horses. The expedition filled every man connected with it with burning shame, and it gave Forrest the most glorious achievement of his career.

Industrial Development and Economic Prosperity

By 1866, the population and commercial interests of the part of the country in which Okolona is located, east of Chuquatonchee Creek, had increased so that in response to the requests of its people the Legislature enacted a law dividing the county into two judicial districts. The eastern part of the county was designated as the Second Judicial District and the western part as the First. It was further provided that equal terms of Circuit and Chancery Courts would be held in each district, one in Okolona, and one in Houston.

Okolona quickly grew and became the major center of trade for Chickasaw County. In the cotton market Okolona was a fierce competitor, virtually controlling the cotton trade of the county. Leading merchants, such as C.C. Dibrell, Buchanan and Son, and Myers and Houseman transferred their business from Houston, Mississippi to Okolona. The railroad increased the processing capacity of Okolona to develop its industry of producing cotton, which allowed for efficient processing of the raw material prior to shipment to market. From 1870 to 1890, the U.S. Census figures indicate that Okolona grew from a population of 1,410 people to 2,099 people, a 49% increase. A map from 1898, from the Atlas of the World indicates Okolona as one of the "Chief Cities" of the state of Mississippi.

From the diary of G.H. Babbitt (born in Okolona in 1877), an entry on August 11, 1897 tells of electricity coming to Okolona. The U.S. Census figures indicate a population growth of 69% between 1900 and 1920. By 1900, Main Street was much as it is today, with a long row of buildings on either side of Main Street between Olive and Gatlin Streets (was Meridian Street at the time). There were over forty businesses in the downtown area by 1904. Among them were blacksmith shops, an ice cream factory, livery stable, a saddle maker, hat shops, an opera house, Chinese laundry, meat stores and hotels. Also, there were dry goods, general merchandise, hardware and furniture stores. Several businesses were labeled "colored" businesses were located primarily on the north side of Main Street, west of what is today Olive Street.

In 1904, there were two hotels and two banks in downtown, one of which is the Merchants and Farmers Bank, built circa 1903. (It was individually listed on the National Register on 14 May 1987.) Shortly after the turn of the century, Okolona acquired a telephone system. In 1907, the first "Horseless carriage" appeared in Okolona. The town continued to prosper through the 1920s and 20s, with a city steam electric plant and four cotton gins. The city's sewage system was installed between 1912 and 1915.



Because most of the older industrial buildings that stood between the railroad and the downtown have been demolished, the district, as it survives today, is illustrative of the development of commerce and residential neighborhoods. Almost all of the contributing residential architecture in the district is a direct result of the prosperity related to the industrial development spawned by the railroad and the commerce the town provided to the Eastern District of Chickasaw County.

Early twentieth century houses range from modest Craftsman and Colonial Revival bungalows to fine examples of such styles as Colonial Revival, Neo-Classical, Queen-Ann, and English Cottage. The houses lie within three blocks of the downtown in all directions.



Okolona is notable for its well-preserved early twentieth century churches and institutional buildings. The churches include the First Methodist Church, built in 1907-08; Grace Episcopal Church, built in 1908; Okolona Presbyterian Church, built in 1919; St. Theresa's Catholic Church, built about 1922; and the First Baptist Church, built in 1924. The Carnegie Library was built in 1915, and the Okolona High School (presently the elementary school) was built in 1924.

Renewal of Okolona


With the Great Depression beginning in 1929 and lasting throughout the 1930s, Okolona was hard hit. The U.S. Census figures indicate a 47% loss in population from 1920 to 1940. All three banks closed and none existed at all for several months. In 1934, the Mobile and Ohio Railroad provided the only major payroll in Okolona. The only substantial new construction during the 1930s was the U.S. Post Office, built in 1937, with Public Works Administration funding.

"Soon after World War II, Okolona experienced a short period of growth. Beginning in the 60's through the 90's, furniture manufacturing was an enormous part of the economy of Okolona. There were some twenty-five plus factories making furniture. During the late 1990's to the present, furniture manufacturing has declined. Presently, there are 12 factories with approximately 1550 employees.