• I found this on Origins of the checkered flag The exact origins of the use of a checkered flag to end races are lost in history, although there are many theories. A possible though unlikely theory is that horse races during the early days of the settlement of the American Midwest were followed by large public meals and that to signal that the meals were ready and racing should come to an end, a checkered tablecloth was waved. Another origin theory claim is that the checkered flag's earliest known use was for 19th century bicycle races in France. A more likely explanation is that a single-colored flag would be less conspicuous against the background of a crowd, especially when early races were run on dirt tracks (and therefore dust reduced the driver's visibility). The earliest known photographic record of a checkered flag being used to end a race was from Long Island, New York in 1904 at the inaugural Vanderbilt Cup race. Some historians dispute the dating of this photograph, and attribute it to the Vanderbilt races of 1906 or 1908. A 2006 publication "The Origin of the Checker Flag - A Search for Racing's Holy Grail", written by historian Fred Egloff and published by the International Motor Racing Research Center at Watkins Glen, traces the flag's origin to one Sidney Waldon, an employee of the Packard Motor Car Company, who in 1906 devised the flag to mark "checking stations" (now called "checkpoints") along the rally-style events of the Glidden Tour. I was going to guess that someone provided a black and white tablecloth to be used at an early auto race. It makes sense to me--the race is over; let's go eat!
  • It is more visible on dirt tracks. The origin of the checkered flag is a mystery shrouded in racing history

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