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

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 bycyclist 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