A charter to construct what eventually became the OH&CC Railroad was granted to the Grenada, Houston & Eastern Railway Company on February 6, 1860, but construction did not begin until 1902, and the first train reached Houston in November 1903. The line from Okolona to Calhoun City was originally known as a branch of the M&O Railroad. On April 20, 1933, the Okolona, Houston & Calhoun City Railroad Company purchased the rail line through a rent-to-own agreement requiring payments of $75 per month for 76 months, totaling $5,700. Besides depots in Okolona and Calhoun City, trains made scheduled stops at Van Vleet, Houston, Pyland, Vardaman, and Derma, while unscheduled flag stops included Kinney, Abernathy, Bacon, Neal, Wilkerson, Parkersburg, Buchanan's Crossing, Hall, and Hollis, where passengers could flag down a train to make it stop. Like many small railroads in the United States during this period, the OH&CC Railroad declined, and after the Interstate Commerce Commission approved its closing on March 24, 1939, the last train ran on Sunday, October 1, 1939.