The tale is based on a story, with some plausible elements, of an incident in Westport, Missouri, in 1853, during America's westward migration. In some versions Windwagon Smith comes sweeping into town with his wind-powered Conestoga wagon complete and working. Other tellings have him inventing the wagon in town, building the craft, and gathering eager passengers, only to have his craft crash or his passengers abandon ship from sea sickness.
By 1850 Westport and nearby Kansas City had displaced Independence, Missouri, as the main outfitting and starting point for traders, trappers, and emigrants heading west on the Santa Fe and Oregon Trails.
Contemporary news accounts have at least three real-life inventors of Land sailing wind-powered wagons in that era. According to the December 1846 issue of the Independence Expositor newspaper, the first was a man named William Thomas. In 1853 Thomas showed a prototype with oversized wheels to the U.S. Army at Fort Leavenworth and formed an Overland Navigation Company. According to Frank Leslie's Illustrated Newspaper, another account involves Oskaloosa sawmill owner Samuel Peppard, who is said to have invented a sailing wagon in 1860 with at least partial success, according to the magazine's description of its arrival in Fort Kearny, Nebraska—250 miles from his starting point.
- Windwagon Smith, Ennis Rees, 1966
- Mary Barile, The Santa Fe Trail in Missouri, p. 96.
- Singhal, Arvind (1987). "Wilbur Schramm: Portrait of a Development Communications Pioneer" (PDF). Communicator. 22 (1–4): 18–22.