7 Hp Duryea was the first automobile attempt to drive from coast to coast, in 1899

Above are a couple of guys with a REO Mountaineer, 1906... and have nothing but the similar cross country in an early car rlevance, to this story that follows (photo from http://www.shorpy.com/node/8903?size=_original )

after the Louise and John Davis car with the backing of two newspapers left New York City they had about made it to Syracuse, and were passed by a one armed bicyclist that had left new York City 10 days after the car had.

Winton tried it 2 years later in May of 1901, but only made it 530 miles from San Fran in route to New York when he was hopelessly stuck in a sand drift