In the autumn of 1838, two Cherokee detachments traveling on the Trail of Tears crossed Richland Creek in Pulaski about two weeks apart. John Benge led one group of nearly 1100 Cherokee with 60 wagons and 600 horses through Pulaski, possibly on October 20-23, during their trek from Ft. Payne, Alabama, to Indian Territory. Following what is now U.S. Highway 31 from Ardmore north to Elkton, they used either the Old Stage Road or the new Elkton-Pulaski Turnpike, then entered Pulaski on what is now U.S. Highway 31. Turning west, they possibly crossed Richland Creek at Mill Street, continued west on Vales Mill Road, turned north at Mt. Moriah Road, traveled alongside Dry Creek on Dry Creek Road, passed through Campbellsville, and went up the valley of Brownlow Creek to Elk Ridge, where they entered Maury County. They then followed a northwestern trek through Tennessee, Kentucky, Missouri, and Arkansas and possibly disbanded on January 17, 1839, near the Woodhall Farm west of the Arkansas state line. A few weeks later, from October 31-November 5, 1838, a second detachment of 650-700 Cherokee with 56 wagons and 318 horses traveled through Giles County and Pulaski. Led by Conductor John Bell, this group began its westward journey at the main Cherokee Agency on October 11th and arrived in Pulaski via Jefferson Street on November 3rd. There they crossed Richland Creek at what is now Mill Street, then followed for about 6 miles the same route the Benge detachment had taken, heading west on Vales Mill Road and then along the main roads now marked by U.S. Highway 64 to Lawrenceburg, crossing the Tennessee River at Savannah, continuing west to Memphis, and crossing the Mississippi River into Arkansas in late November. The Bell detachment traveled west and northwest to Little Rock and to the Vineyard Post Office, now Evansville, on the border of Indian Territory, where it was disbanded on January 7, 1839, in Arkansas to avoid encounters with anti-treaty Cherokee detachments in Indian Territory.