What's the craziest thing you've ever done on a bet? Shaved your head? Snuck into a party when you weren't on the guest list? Played Russian Roulette with some enforcers from a Mexican drug cartel? (I would advise against the last one, personally. Things tend to go south a lot faster than you might expect.)

Whatever you've done on a bet, it's not as awesome as what Dr. Horatio Nelson Jackson did 110 years ago. On a whim and the desire to win $50, Jackson wagered that he could drive from one coast to another in an automobile, a feat that had never been done before and was largely considered impossible by many.


With the help of a 20 horsepower Winton touring car, a mechanic friend and a bulldog in racing goggles, Jackson made the impossible possible. Here's how he did it.

Before we get into Jackson's journey, let's talk about what America was like in 1903. Teddy Roosevelt was president, the first transatlantic radio broadcast had just been made, and the "horseless carriage" was still in its infancy. This was five years before Henry Ford's Model T brought motoring to the American masses, so cars were essentially still just playthings for the very wealthy. At the time of Jackson's trip, very few Americans had ever even seen an automobile before. (Motorsports were also in their infancy; that same year, the Paris-Madrid Race was held, killing eight people in the process.)

So the odds were definitely against Jackson, a wealthy gentleman and physician from Vermont who made this money the good old fashioned American way. No, not suing people! The other one — he married rich.


But Jackson was our kind of people, make no mistake about it. If Jalopnik had existed in the early 1900s, he probably would have been a contributor. He had this extremely optimistic, can-do attitude about everything and was more than willing to face the hardships involved with driving across the country.

As PBS tells it, Jackson was 31 at the time of the drive, and while he gave up practicing medicine in 1900 after a bout of tuberculosis, he wasn't hurting for money as his wife Bertha was their heiress to a cure-all tonic empire. The beverage, if you're curious, was called "Payne's Celery Compound" and it was 20 percent grain alcohol. (Regardless of what ailed you, I have no doubt that "compound" would make you feel a lot better.)

The story goes that Jackson undertook his journey after making a bet with a group of men in a San Francisco bar. History says that the other men argued that the automobile was a passing fad, and that it would be impossible to travel in one from there to New York in less than 90 days. Jackson said he could pull it off, and then someone bet him $50 he couldn't.

With the modern equivalent of about ONE MILLION DOLLARS $1,250 on the line, Jackson set out to prove them wrong. But while he was already an automotive enthusiast, he needed a special kind of car to get the job done.

His mechanic (and later co-driver) Sewall K. Crocker suggested a Winton. Back then, Cleveland's Winton Motor Carriage Company made cars that had a reputation for being tough and reliable. They bought a slightly used Winton Touring Car for $3,000 from a local Wells Fargo executive with a two-cylinder, 20 horsepower engine. (PBS says that Winton made 850 of them in 1903, bringing the nation's total registered cars to just 33,000.) Their rig included sleeping bags, rain coats, tools, a shotgun and a rifle, and a small camera to record the trip.

And with that, on May 23, Jackson and Crocker were off. They went north from San Francisco into Oregon and then east through the northern United States, passing through Wyoming, Nebraska, and Chicago along the way. Keep in mind that a journey like this one was was made even harder because roads were essentially nonexistent compared to what they're like today.


The encountered floods. They ran out of cash. They fixed or replaced nearly every part on the Winton. Local blacksmiths helped them weld on new parts. They crashed the car at least once, but thankfully, it wasn't serious.

The National Museum of American History says the two men used a block and tackle pulley system to extract the car when it got stuck in the mud. When it broke down, they wrote or telegraphed the factory asking for more parts and waited for them to be delivered by train.

Along the way, they acquired Bud, a bulldog who became their racing goggles-wearing companion and possibly the first dog to experience the joys of car travel — at least, in America, maybe.


As they traveled Jackson and Crocker found themselves making headlines in newspapers and magazines, not to mention generating a massive amount of publicity for Winton. No one had ever done what they were doing before, and many people along their route came out to get their first look at an actual automobile. Sometimes, other early automobile owners would come out and join them for a spell along their route.

In addition, Packard and Oldsmobile also dispatched their own teams to try and complete the trip as well, although they left after Jackson and Crocker did.

After a journey that was long and extremely arduous, and caused Jackson to lose 20 pounds along the way, the duo (and canine) made it into New York in the early morning hours of July 26. I'll let that article from PBS take it here:

It was 4:30 in the morning on Sunday, July 26th, when Jackson, Crocker and Bud crossed the Harlem River into Manhattan, drove down the city's deserted streets, and finally honked their horn to awaken the night porter at the Holland House hotel on 30th Street and 5th Avenue.

Jackson had made it from San Francisco in 63 days, 12 hours, and 30 minutes - well within his wager of 90 days. And having become the first to drive a car across the nation, within hours of their entrance into New York, he and Crocker and Bud were the toast of the town.

In total, Jackson spent about $8,000 on the trip, which is close to $200,000 today. He never collected his winnings from the guys at the bar in San Francisco.


As cars became more common in the 1910s and 1920s, Winton had a lot of trouble keeping up with the competition. They eventually ceased production and became a subsidiary of General Motors, where they made engines for boats.

As for Jackson, his life of derring-do continued well after the drive ended. He retired to Vermont with Bud and his wife for a time. Then he enlisted in the Army when World War I broke out and came back a decorated hero, despite being well into his 40s when he entered the service. He donated his Winton to the Smithsonian Institution in Washington and would regale anyone who would listen about the drive that made history, according to PBS. (Bud's racing goggles are on display there too.)

To celebrate the 100th anniversary of Jackson and Crocker's drive, documentary filmmaker Ken Burns directed the film Horatio's Drive: America's First Road Trip for PBS in 2003. Much of what you read here comes from PBS' fantastic website about the drive, which goes into far more detail than I can. I'd encourage you to watch the film next time it's on as well.


Also, antique auto owners repeated this feat in 2003. Maybe we'll see some people do it again this year on the 110th anniversary.

One last thing about Jackson. He died in 1955 at the age of 82, and the world had changed tremendously in his lifetime. By then cars had transformed from a novelty into a global industry. Once, they were slow-moving horseless carriages; now, they were sleek and colorful rocket-shaped rides that represented all the optimism that postwar America had to offer. And they would only continue to get faster as the decades went on. In 2006, Alex Roy did it in just 32 hours.

I have a feeling that if Jackson were still alive, he'd be the first to try and beat that.

Photos credit Getty Images, AP, Public Domain

Hat tip to reader "I'd walk for my car," whose comment on the "Tell Us Something We Don't Know" story inspired this feature!