This crossing of the Elk River on the Columbia, Pulaski, Elkton, and Alabama Turnpike, earlier called the Bumpass Trail, was the narrowest place that could be bridged between Fayetteville, Tennessee, and Florence, Alabama. During the Civil War, a wooden bridge stood here and was vital to the movement of both Federal and Confederate troops. On November 6-7, 1863, Union Gen. William T. Sherman and his army marched through Elkton on the way from Memphis to Chattanooga, stopped overnight, and according to local tradition made his headquarters in the Reason's Inn, Cabinet & Coffin Manufacturing at the corner of Main and Market Streets. Sherman wrote to Gen. George Crook that the Elk River was a major obstacle, saying, "Even as high up as Elkton where your officer passed it is nearly swimming to a horse." The nearby Old U.S. Highway 31 intersection includes an earlier turnpike. On September 26, 1864, Confederate Gen. Nathan Bedford Forrest and his troops rode by after a successful attack at Athens, Alabama, and Forrest wrote that with horses captured at Athens and Sulphur Springs trestle he was able to mount troops who had been marching on foot and replace others whose horses had given out; he ordered Gen. Buford to move along the dirt road parallel with the railroad through Prospect, west of Elkton, while with the balance of his command he moved to Elkton and then directed his course toward a Government corral at Brown's plantation toward Pulaski, 3 miles north of here.