For a $50 bet, Horatio Nelson Jackson set out from San Francisco in 1903 to cross the country by car in 90 days, challenging the belief that the newfangled “horseless carriages” were an impractical and unreliable means of travel. Though he did not own a car and had practically no driving experience, Jackson enthusiastically struck out for New York with his mechanic and a two-cylinder, 20-horsepower Winton Touring Car named the Vermont. A blowout 15 mi. into their journey was the first of many mechanical setbacks encountered along their often-unpaved route, but Jackson persevered, winning the hearts of the public and acquiring a goggle-sporting bulldog named Bud along the way. Sixty-three days, 12 hours, and 30 minutes after they began, the triumphant trio crossed the Harlem River into Manhattan. The media raved about the trip’s success, and Americans began to reconsider the possibilities of the automobile. Thus, the great American roadtrip was born.