In this earliest known day-by-day journal of a cattle drive from Texas to Kansas, Jack Bailey, a North Texas farmer, describes what it was like to live and work as a cowboy in the southern plains just after the Civil War. We follow Bailey as the drive moves northward into Kansas and then as his party returns to Texas through eastern Kansas, southwestern Missouri, northwestern Arkansas, and Indian Territory. For readers steeped in romantic cowboy legend, the journal contains surprises. Bailey’s time on the trail was hardly lonely. We travel with him as he encounters Indians, U.S. soldiers, Mexicans, freed slaves, and cowboys working other drives. He and other crew members—including women—battle hunger, thirst, illness, discomfort, and pain. Cowboys quarrel and play practical jokes on each other and, at night, sing songs around the campfire. David Dary’s thorough introduction and footnotes place the journal in historical context.