There is always a plan of sorts to every road trip.

Dr. Horatio Nelson Jackson, on perhaps the first true American road trip, had a plan. On May 18, 1903, he accepted a $50 wager, at a gentlemen's club in San Francisco, that he could not drive across America by a fledgling invention – the automobile. Yet he did just that in 63 1/2 days. He had averaged 1.93 mph when he pulled into New York City on July 26, 1903 in a dusty Winton ...