In 1903, one doctor bet $50 he could drive from San Francisco to New York.
Today, planning a cross-country road trip can take only a few hours. In 1903, there were no interstate highways, no gas stations, almost no useful road maps, and only about 150 miles of paved roads across the entire United States. All of them were inside cities.
Most roads were little more than dirt trails built for horses and wagons. Many Americans still saw the automobile as an expensive novelty that might never become a practical way to travel.
Then Horatio Nelson Jackson put $50 on the table.
On May 19, 1903, Jackson, a 31-year-old Vermont doctor who had left medical practice after recovering from tuberculosis, was visiting San Francisco with his wife, Bertha. At the University Club, he happened to hear a discussion about the future of the automobile.
The prevailing opinion was that cars were unreliable toys and that nobody would drive one across the continent.
Jackson disagreed.
He accepted a $50 wager that he could reach New York by automobile in less than 90 days.
There were a few problems.
Jackson didn't own a car. He had very little driving experience. He had no prepared route.
Four days later, he left anyway.
Jackson bought a used 1903 Winton and named it Vermont after his home state. The open touring car made about 20 horsepower and offered little protection from the weather.
He hired Sewall K. Crocker, a 22-year-old mechanic and former professional bicycle racer who had recommended the Winton for the trip.
They loaded the car with tools, spare parts, sleeping bags, blankets, rain gear, weapons, a Kodak camera, and as much fuel and oil as they could carry.
On the afternoon of May 23, 1903, Jackson and Crocker drove along Market Street, crossed San Francisco Bay by ferry and headed east toward New York.
They made it about 15 miles beyond Oakland before a tire blew.
Their only spare tire was now gone.
America's first cross-country automobile journey had barely begun.
Bad roads were only part of the problem.
Across large parts of the West, there was nothing resembling the road network a modern driver would recognize.
Jackson and Crocker followed trails, asked local residents for directions and used railroad tracks as landmarks. When necessary, they drove directly along railroad tracks and trestles.
East of the Mississippi River, useful road maps were particularly difficult to find.
Jackson also deliberately headed north instead of taking a more direct route through Nevada and Utah. Earlier attempts had shown how dangerous deep desert sand could be for an early automobile.
So the Vermont traveled through Northern California, Oregon and Idaho before turning east across Wyoming.
The detour did not make the journey easier.
By May 27, Jackson and Crocker were climbing rough mountain trails in Northern California where automobiles had never traveled.
They moved boulders by hand, repeatedly repaired the clutch, patched punctured inner tubes and pumped up the tires. Streams often had no bridges, forcing them to drive directly into the water and hope the car made it to the other side.
One crossing was simply too deep.
The car became stuck.
Jackson and Crocker stripped down, waded across the stream with their block and tackle, attached it to a tree and used a cable to pull the Winton free.
Their equipment was disappearing almost as quickly as the miles were adding up.
Jackson lost his glasses and fountain pen. On another occasion, Crocker crawled underneath the car to clear a clogged oil line and ended up covered in about two gallons of oil.
Still, by the time they reached Alturas, California, Jackson was becoming increasingly convinced that the car could make it all the way.
Local residents weren't sure what they were seeing.
Many had never seen an automobile before. Crowds gathered around the Vermont wherever it stopped.
One woman reportedly gave the travelers deliberately incorrect directions so relatives farther down the road would have a chance to see the car.
Then the journey became a race.
On June 20, Tom Fetch and Marius Krarup left San Francisco in a 12-horsepower 1903 Packard Model F.
Unlike Jackson's improvised adventure, the Packard expedition had been planned for months. Fetch was a company test driver, while Krarup was a journalist for Automobile Magazine.
Their route had been mapped out in advance. Supplies were positioned along the way, luggage was shipped by train, and a Packard mechanic provided additional support.
Packard wasn't simply trying to cross America.
It was a publicity campaign.
During part of the chase, Fetch and Krarup covered roughly twice as many miles per day as Jackson. By early July, despite leaving nearly a month later, they had dramatically reduced the gap.
But Packard's carefully planned route created a problem of its own.
The company's advertising director had routed the car through scenic parts of Utah and Colorado because he believed the landscapes would make better advertising photographs.
That sent the Packard through rugged canyon country and the Rocky Mountains.
Then another car entered the race.
On July 6, a third automobile left San Francisco.
Experienced motorists and mechanics Lester Whitman and Eugene Hammond set out in a much smaller 1902 Oldsmobile Curved Dash Runabout, another manufacturer-backed attempt to make history.
Now three cars were racing east.
The Oldsmobile initially moved quickly through the Sierra Nevada and into Nevada. But mechanical problems soon erased its advantage.
At one point, a broken part left the little Oldsmobile able to move backward but not forward.
Jackson suddenly had an advantage worth protecting.
At 4:30 a.m. on July 26, the Vermont entered Manhattan.
The final numbers were remarkable: roughly 5,600 miles, 63 days, 12 hours and 30 minutes, and $8,000 of Jackson's own money.
According to PBS, the trip consumed about 800 gallons of gasoline.
The $8,000 total included the car, Crocker's wages, fuel, food, lodging, tires, spare parts and even the $15 they spent on Budweiser.
Jackson also lost about 20 pounds.
The New York Herald described the Winton as covered in mud and badly battered after the punishing journey. Its mudguard was broken and the front axle was bent, but the car had reached its destination.
Packard eventually reached New York.
Fetch and Krarup arrived about two weeks after Jackson. Ironically, their total travel time was roughly a day and a half shorter than Jackson's.
But they had left San Francisco nearly a month later.
They still finished second.
The Oldsmobile came in third.
Whitman and Hammond reached New York on September 17 after spending 73 days on the road. They then continued north to Boston, where they lowered the Oldsmobile's front wheels into the Atlantic Ocean.
That allowed the company to claim its own publicity milestone: the first automobile crossing from sea to sea.
By the end of 1903, three automobiles had crossed the United States.
The question was no longer whether it could be done.
The question was how fast it could be done.
The original 1903 Winton Vermont survives in the collection of the Smithsonian's National Museum of American History, along with Bud's tiny driving goggles.