the first automobile to successfully transit the North American continent, a Winton. The trip cost about 8000 dollars then, about 300,000 in todays dollars

in 1903, Horatio Nelson Jackson, a physician and automobile pioneer, and Sewall Crocker arrive in New York, successfully completing the first continental crossing by car, a journey prompted by a $50 bet to determine whether a car could successfully be driven across the U.S.

Dr. Jackson was a 31-year-old auto enthusiast who differed with the then-prevailing wisdom that the automobile was a passing fad and a recreational plaything. 

 The wealthy young doctor, who had retired at age 28 (his wife, Bertha Jackson, had inherited a fortune from her father who founded a popular cure-all called Paine’s Celery Compound), had stopped in San Francisco after a long trip to buy two automobiles and learn how to drive.

While in San Francisco's University Club as a guest on May 18, 1903, he agreed to a $50 wager ($1299 in today's dollars) to prove that a four-wheeled machine could be driven across the country. Having no mechanical experience, Jackson convinced a young mechanic and chauffeur, Sewall Crocker, to serve as his travel companion, mechanic, and backup driver. 

Jackson purchased a slightly used two-cylinder Winton touring car from a Wells Fargo executive for $3,000 (about $100,000 today). He loaded it up with cooking and camping gear, a rifle and an ax, an extra gas tank, and a block and tackle to use if the car got stuck. With the 225-pound Jackson and the 150-pound Crocker on board, the fully loaded car weighed more than 3,000 pounds. Jackson christened the vehicle the Vermont, after his home state.

Along the way, the two picked up a pit bull and they named him Bud. Their trip took sixty-three days, twelve hours, and thirty minutes after commencing their journey in San Francisco

Their trip started off auspiciously enough. Despite blowing a tire after just 15 miles, they made it to Tracy the first night, having covered 83 miles. But then one mishap after another befell them. On the way to Oroville, they noticed that their cooking gear had fallen off the car. Then they got lost and asked a redheaded young woman riding a horse directions to Marysville. She pointed down a road. “We took that road and drove down it for about 50 miles and then it came to a dead end at an isolated farmhouse,” Jackson recalled. “The family all turned out to stare at us and told us we’d have to go back. We went back, and met the red-haired young woman again. ‘Why did you send us way down there?’ I asked her. ‘I wanted paw and maw and my husband to see you,’ she said. ‘They’ve never seen an automobile.’”

They didn't know it, but Packard had planned to do the same thing a few weeks later, and so, both parties were cross the continent at the same time

https://www.facebook.com/automotivehistory  http://misleddit.com/p/2swauj/

this entire trip is very well covered by a documentary movie: Horatio's Drive


you can find some of it on Youtube, or get it from Netflix

http://www.vintag.es/2017/02/it-all-started-with-50-wager-two-men.html

https://www.sfchronicle.com/bayarea/article/road-trip-sf-ny-17232273.php
https://www.sierrasun.com/news/first-automobile-over-the-sierra-stopped-short-of-transcontinental-trip/