65 Days, Zero Roads, and One Very Confused Dog: The First Drive Across America

Somewhere in the Nevada desert in the summer of 1903, a man named Horatio Nelson Jackson was sitting in a 20-horsepower Winton automobile, covered in dust, staring at what the map optimistically called a road. It was not a road. It was a cattle trail. And he still had roughly 3,000 miles to go.

Today, a coast-to-coast drive takes about 40 hours of actual driving time. You can do it in four or five days if you push it, or knock it out in a long week if you want to stop somewhere interesting along the way. You'll have GPS, interstate highways, rest stops every 50 miles, and a gas station practically whenever you need one. Jackson had none of that. He had a map that was mostly guesswork, a mechanic named Sewall Crocker, a borrowed pair of goggles, and eventually — improbably — a dog.

The Bet That Started Everything

Jackson was 31 years old and, by most accounts, the kind of person who made decisions quickly and dealt with consequences later. While staying in San Francisco, he got into a conversation at a gentlemen's club about whether an automobile could cross the country. Someone said it couldn't be done. Jackson bet $50 that it could — and that he personally would do it.

He had almost no driving experience. He bought the Winton on the spot, hired Crocker as his mechanic, and set off on May 23, 1903. There was no route planned. There was no route to plan. The United States in 1903 had approximately 150 miles of paved road in the entire country, and almost none of it was outside city limits.

The rest was dirt, mud, sand, rock, and whatever else the landscape decided to throw at them.

What 'The Road' Actually Meant in 1903

Here's the thing modern drivers struggle to fully absorb: there was no such thing as a national road network. When Jackson left San Francisco heading east, he wasn't following a highway. He was following suggestions. Sometimes those suggestions came from locals who pointed vaguely at a horizon. Sometimes they came from maps that had been drawn by people who had never actually traveled the routes they were illustrating.

Rivers had no bridges. The car had to be hauled across by whatever means were available — rope, ferry, sheer stubbornness. Mud was a constant enemy. The Winton got stuck so many times that pulling it free became a routine part of the day. On some stretches, the men drove through the night because stopping meant sinking.

Parts broke constantly. There were no auto parts stores. When something failed, Jackson and Crocker either improvised a fix or waited — sometimes days — for a replacement part to be shipped from the nearest city. At one point in Wyoming, they were stranded for nearly a week.

Enter the Dog

Somewhere in Idaho, the two men adopted a stray bulldog they named Bud. Whether this was an act of loneliness or genuine affection is lost to history, but Bud became the third member of the crew and, by most accounts, the most photogenic.

Bud also had a problem: the dust. It was relentless and blinding out on the open trail, which is why Jackson and Crocker wore goggles. So they got a pair for the dog, too. Photos of Bud wearing his driving goggles became some of the most reproduced images of the entire journey — a small, absurd detail that somehow captures the whole spirit of the adventure. These three figures, caked in dust, completely improvising their way across an unmapped continent.

Sixty-Five Days Later

Jackson rolled into New York City on July 26, 1903. The trip had taken 63 days and 12 hours of actual travel time — often cited as 65 days total including rest. He'd covered roughly 5,600 miles, spent around $8,000 (a staggering sum at the time, far more than the $50 bet), and worn through multiple sets of tires.

He won the bet, technically. But the money was never really the point.

Two other teams attempted the same crossing that same summer, which tells you something about the moment America was in. The automobile was new, the country was restless, and people were starting to sense that these machines might actually change everything.

What Changed, and How Fast

Within a decade of Jackson's trip, automobile ownership was growing rapidly and pressure was mounting for better roads. The Lincoln Highway — the first named transcontinental route — was established in 1913, just ten years after Jackson's ordeal. It wasn't fully paved for years after that, but it was a start.

By the 1950s, the interstate highway system was being planned and funded. By the 1970s, you could drive coast to coast on a continuous network of controlled-access highways without hitting a single traffic light if you chose your route carefully.

Today, the same journey that nearly broke Horatio Jackson is a fairly unremarkable thing to attempt. People do it every summer in rental cars, with podcasts playing and fast food cups in the holder. The roads are smooth, the route is obvious, and the biggest inconvenience is usually a construction zone somewhere in Ohio.

The Absurdity of the Timeline

What's genuinely hard to process is how recent all of this is. Jackson's trip was in 1903. Your grandparents — or great-grandparents, depending on your age — were alive in a country where driving to the next state was a serious undertaking and crossing the continent was considered nearly impossible.

The transformation from 65-day ordeal to 40-hour drive didn't take centuries. It took one human lifetime.

Bud the dog never knew what he started. But somewhere between those Nevada cattle trails and the I-80 overpass you crossed last week, America quietly became a nation that drives everywhere, takes roads for granted, and barely remembers a time when there weren't any.