Tennessee Street along the north side of the square was originally part of Gaines' Trace, a horse path laid out in 1807 under the direction of Capt. Edmund Pendleton Gaines of the U. S. Army. From Melton's Bluff on the Tennessee River, the trace ran westward to Cotton Gin Port on the Tombigbee, in present-day Mississippi. Another important early thoroughfare was the Byler Road (1819), which ran southward through Courtland and linked the Tennessee Valley to Tuscaloosa and lower Alabama.
Seeking a means to ship cotton and other goods around the treacherous Muscle Shoals of the Tennessee River, area planters and merchants met at Courtland in 1831 to consider a rail line. On January 13, 1832, the 50-mile long Tuscumbia, Courtland & Decatur railroad was chartered. Early trains were usually horse-drawn, although an English-made steam locomotive was acquired in 1834.Absorbed by the Memphis & Charleston line after 1850, the railway was largely destroyed during the Civil War. The rebuilt railroad became part of the Southern system in 1898.