Today, a cross-country road trip can be planned in minutes. In 1903, there were no Interstate highways, no gas stations, virtually no useful road maps for the West, and only about 150 miles of paved road in the entire United States—all of it inside cities. Most roads were dirt tracks built for horses and wagons. Many Americans still considered the automobile an expensive novelty that might never become practical transportation.

Then Horatio Nelson Jackson put $50 on the table.

On May 19, 1903, Jackson, a 31-year-old Vermont physician who had given up his medical practice after a bout of tuberculosis, was visiting San Francisco with his wife, Bertha. At the University Club, he overheard a debate 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 and accepted a $50 wager that he could reach New York by automobile in less than 90 days.

There was an obvious problem.

Jackson didn't own a car.

He also had little experience driving one, had no route prepared, and had never crossed the country by automobile—because nobody had.

Four days later, he left anyway.

A Car, a Mechanic and No Real Plan

Jackson bought a used 1903 Winton touring car and named it Vermont after his home state. The open touring car produced about 20 horsepower and offered little protection from the weather. Jackson 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, rubber clothing, weapons, a Kodak camera and whatever fuel and oil they could carry. Bertha sensibly returned east by train.

On the afternoon of May 23, 1903, Jackson and Crocker drove down Market Street, crossed San Francisco Bay by ferry and pointed Vermont toward New York.

They made it about 15 miles beyond Oakland before blowing a tire.

Their only spare was now gone.

America's first road trip was underway.

Meet the Crew

Horatio Nelson Jackson

The Driver

A 31-year-old Vermont doctor and automobile enthusiast who accepted the $50 bet despite owning no car and having little driving experience. Jackson financed the entire expedition and supplied the determination—and money—that kept it moving.

Bud

The Navigator(ish)

A bulldog Jackson bought for $15 in Caldwell, Idaho, roughly three weeks into the trip. Fitted with goggles to protect his eyes from dust, Bud became the crew’s mascot and eventually one of the most recognizable faces of America’s first road trip.

Sewall K. Crocker

The Mechanic

A 22-year-old mechanic and former bicycle racer who recommended the Winton and became the expedition’s mechanical lifeline. Crocker repaired everything from broken engine parts to failed wheel bearings, often improvising fixes far from a proper shop.

There Wasn't Really a Road to Follow

The problem wasn't simply that America's roads were bad. In huge sections of the West, the kind of connected road system a modern driver would recognize effectively didn't exist.

Jackson and Crocker followed wagon trails, asked locals for directions and used railroad lines as navigational guides. When necessary, they drove directly along railroad rights-of-way and over railroad trestles. Beyond the Mississippi, useful road maps were especially scarce.

Jackson also deliberately headed north instead of taking a direct route through Nevada and Utah. Previous attempts had demonstrated how dangerous deep desert sand could be for an early automobile, so Vermont traveled through Northern California, Oregon and Idaho before turning east through Wyoming.

The detour did not make the trip easy.

It merely changed the problems.

The Mountains Tried to End the Trip Early

By May 27, Jackson and Crocker were climbing rough mountain trails in Northern California that had never seen an automobile. They removed boulders by hand, repeatedly repaired the clutch, patched punctured inner tubes and pumped the tires back up manually. Streams often had no bridges, forcing them to simply drive into the water and hope the Winton reached the other side.

One crossing was too deep.

The car became stuck, so Jackson and Crocker stripped off their clothes, waded across with their block and tackle, attached it to a tree and pulled the Winton out with rope.

Their equipment was disappearing almost as quickly as the miles passed. Jackson lost spectacles and a fountain pen. Crocker once crawled under the car to clear a clogged oil line and had roughly two gallons of oil pour over him. He finished the day wearing Jackson's clothes.

Yet when they reached Alturas, California, Jackson was increasingly convinced the car could make it.

The locals weren't so sure what they were looking at. Many had never seen an automobile. Crowds gathered around Vermont wherever it stopped.

That reaction would follow them across the country.

63 Days Across America

The Road Trip Got Weird

The mechanical failures tell only half the story. In 1903, simply seeing an automobile could be an event.

A woman reportedly deliberately misdirected Jackson and Crocker so relatives farther down the road would get a chance to see a car. Cowboys used horses and lariats to rescue Vermont. Ranch families traded food for rides. In one Idaho town, gambling stopped when the automobile arrived. One Oregon traveler apparently mistook the approaching Winton for a train that had somehow left the tracks and hid beneath his wagon.

Then there were the smaller indignities: Jackson repeatedly lost his glasses as the car bounced along; Crocker was covered in engine oil; they slept in horse stalls rather than questionable bedding; their gasoline leaked away; they ran over a skunk immediately before checking into a hotel; Jackson lost his coat and cash; and a piece of farm machinery eventually became part of America's first transcontinental automobile.

Bud became a celebrity in his own right. He rode at the front of the Winton wearing goggles to protect his eyes from dust and eventually appeared with Jackson and Crocker in some of the trip's most famous photographs. Jackson joked that Bud was the only member of the trio who completed the journey without swearing.

By the time the travelers reached the East, crowds and newspapers were waiting for them.

The automobile itself had become the attraction.

Then It Became a Race

Jackson's trip began as a private bet.

It didn't stay that way.

On June 20, while Jackson was lost in Wyoming, Tom Fetch and Marius Krarup left San Francisco in a 12-hp 1903 Packard Model F. Unlike Jackson's improvised adventure, Packard's expedition had been planned for months. Fetch was a company test driver; Krarup was a journalist for Automobile Magazine. Their itinerary had been mapped in advance, supplies were positioned along the route, luggage traveled ahead by train, and a Packard machinist provided additional support.

Packard wasn't merely trying to cross America.

It was staging a publicity campaign.

And it worked—almost too well.

Fetch and Krarup moved roughly twice as many miles per day as Jackson during part of the chase. By early July, despite leaving nearly a month later, they had closed the gap considerably.

But Packard's carefully planned route became its own problem.

The company's advertising director had routed the car through spectacular sections of Utah and Colorado because the scenery would produce better publicity photographs. The result was brutal terrain through canyons and the Rockies. The man responsible later admitted that he had prioritized publicity over practicality.

The supposedly organized corporate expedition had made the same basic mistake Jackson repeatedly made:

It chose the wrong road.

And Then Oldsmobile Joined In

On July 6, a third car left San Francisco.

Experienced motorists and mechanics Lester Whitman and Eugene Hammond set off in a much smaller 1902 Oldsmobile Curved Dash Runabout, another manufacturer-backed attempt to claim the transcontinental prize.

Now there were three cars racing east.

The Oldsmobile initially moved quickly across the Sierra Nevada and into Nevada, but breakdowns soon destroyed its momentum. At one point, a failed component left the little Oldsmobile capable of moving in reverse but not forward.

Jackson suddenly had a lead worth protecting.

The First One to New York

At 4:30 on the morning of July 26, Vermont crossed into Manhattan.

The final tally was extraordinary: approximately 5,600 miles, 63 days, 12 hours and 30 minutes, and $8,000 of Jackson's own money. PBS's account puts the fuel consumption at about 800 gallons of gasoline; Atlas Obscura's later retelling gives 600 gallons, so the surviving secondary accounts conflict on that figure. The $8,000 total included the car, Crocker's salary, fuel, food, lodging, tires, replacement parts and even the $15 paid for Bud.

Jackson had also lost about 20 pounds.

The New York Herald described the Winton as mud-covered and battered after its 5,600-mile journey. The car had a broken mudguard and sprung front axle, but it had made it.

And the $50?

Jackson never collected it.

What Happened to Packard and Oldsmobile?

Packard did eventually reach New York.

Fetch and Krarup arrived roughly two weeks after Jackson. Ironically, their total elapsed crossing time was about a day and a half shorter than Jackson's—but because they had left San Francisco nearly a month later, they were still second across the country. A fleet of Packards escorted them into New York.

Oldsmobile came third.

Whitman and Hammond reached New York on September 17, after 73 days on the road. They then continued north to Boston and dipped the Oldsmobile's front wheels into the Atlantic, allowing the company to claim the publicity-friendly distinction of the first "sea-to-sea" automobile crossing.

By the end of 1903, three automobiles had crossed the United States.

The question was no longer whether it could be done.

It was how quickly it could be done.

The Trip Wasn't Even Over

After conquering the continent, Jackson still had to get home.

On July 30, he and Bertha—with Bud aboard—left New York in Vermont for Burlington. Naturally, the car continued breaking.

The low-speed clutch failed in Hudson. The high-speed clutch failed in Albany. A breaker box failed in Middlebury. Near Burlington, Jackson's brothers came out in another automobile to escort him home—and their car broke down instead.

Jackson hooked their disabled car to Vermont and towed them the final miles.

Then came the perfect ending.

On August 7, Jackson finally pulled into his stable in Burlington. As Vermont crossed the threshold, its drive chain—one of the few major components that had survived the entire transcontinental trip without failing—snapped in two.

Two months later, Jackson was back behind the wheel.

On October 3, 1903, the man who had just driven across an entire continent was arrested in Burlington and fined $5 plus court costs for exceeding the local six-mile-per-hour speed limit.

What Happened to Vermont?

Jackson kept the Winton for decades and eventually donated it to the Smithsonian in 1944.

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.

Its importance goes well beyond being an old car that survived.

Jackson, Crocker and Bud had demonstrated that an automobile could provide something the railroad could not: individual freedom over enormous distances. The Smithsonian credits the pioneering journey with helping change Americans' perception of long-distance automobile travel; within a decade, serious plans for coast-to-coast highways were underway.

In 1903, driving across America sounded ridiculous.

By the end of that same year, three cars had done it.

Within a generation, Americans would be packing their own cars, choosing their own destinations and heading across the country simply because they could.

Jackson spent $8,000 to win a $50 bet he never collected.

What he actually proved was worth considerably more: America could be driven.