The First American Road Trip

A man, his bulldog, and the 3,000 mile race to be the first to drive from San Francisco to New York
Hero horatio roadtrip header

Feb 25, 2015 | By Liv Combe

t started, as many good stories do, with a bet.

It was May of 1903, and Horatio Nelson Jackson was having drinks at the University Club in San Francisco. The talk that evening naturally centered around current events — President Theodore Roosevelt, whether or not the Boston Pilgrims would win the pennant, and the emergence of a new-fangled machine that had just begun to make its way onto the streets of major American cities: the automobile

“The majority opinion,” Jackson later wrote, “was that save for short distances, the automobile was an unreliable novelty, a passing mechanical fancy which thinking men could do no other than discard, as the horse continued to demonstrate his proper place as the dependable servant of mankind for travel.”


The 31-year-old Jackson had an adventurous streak — he’d recently visited Mexico and Alaska and already had two automobiles to his name. He was learning how to drive them in California before he shipped them back home to Vermont and his waiting wife, Bertha. She was the funds behind the operation, her family fortune more than supported the two of them since Jackson gave up his medical practice three years earlier after contracting tuberculosis. 

So when someone wagered him $50 (ed. around $1300 in the early 1900s, by inflation) that a journey across the country in this newfangled “rich man’s toy” could never be completed, Jackson jumped on it. He had money. He had time. So four days later, Jackson set out. And the first American road trip was born.

At this time, the automobile was as new and innovative as Tesla is today — but without the culture and infrastructure of an entire country behind it to justify its worth. In 1903, there were only 150 miles of paved roads in the entire United States, and most of them were within major city limits, leaving vast chunks of the country unconnected. There were no gas stations and there were no detailed maps, especially when it came to driving routes. Cars were noisy, dangerous, and expensive — costing up to $6,000 at a time when the average American was bringing in about an eighth of that annually.


When we think of the road trip today, we think of Jack Kerouac, of Easy Rider, of playlists and gas station beef jerky and Instagramming sunsets from I-80. No such things were going to happen as Jackson prepared for his journey.

In Vermont, a law had been enacted that required every automobile to be preceded down the street by an adult waving a red flag. In Tennessee, drivers had to give a week’s notice before heading out on a trip. By the end of the 1800s, there were only eight thousand cars in the United States and 14 million horses; in 1903, the total car registration in the country was at 33,000.  Jackson was pitting himself against a vast majority of people who assumed that this automobile was going nowhere fast — much less 3,000 miles from coast to coast. 

In preparation for his trip, Jackson hired a mechanic, Sewall Crocker, a 22-year-old cyclist from Washington, to ride with him and keep the car running. For their vehicle, the two settled on a 1903 Winton, manufactured in Cleveland, Ohio and bought from a San Francisco Wells Fargo executive who overcharged the duo by $500 from the vehicle's $2,500 list price. 


The Winton could go up to 30 miles per hour. It had no windshield, no top, and the steering wheel was on the right. It could hold eleven gallons of gas in its tank, sufficient to drive 175 miles — which, hopefully, would take Jackson to the next small-town general store, since gas stations didn’t emerge until 1905 and there was nowhere else to fuel up once their spare tank ran dry. They removed the back seat and piled their equipment and luggage onto the vehicle, which Jackson dubbed 'the Vermont.' 

Four days after the wager was made, Jackson and Crocker took the ferry from San Francisco to Oakland and set out on their journey east. Jackson had enthusiastically planned on going 200 miles per day, but the reality of the situation soon sunk in, as the duo were beset with delays, including breakdowns, running out of gas, backtracking from poor directions, and flooded and snowed-in roads. The car was crawling along. At one point, a cowboy's horse had to pull them to civilization when the car got too clogged with desert dust and wouldn’t start.

The bright spot? In Idaho, Jackson added a third member to their party — Bud the bulldog, purchased for $15, and described by Jackson as “the one member of our trio who used no profanity on the entire trip.” 


In every town they passed through, locals gawked at the new machine rattling around and newspapers printed headlines marking the occasion of “the first live auto” rolling through town. The farther they went, the more public interest grew. And then it skyrocketed when, on June 20, two more men set out from San Francisco, intent on beating Jackson and his dog to New York. 

If Jackson and the Vermont were David, the new challengers would be Goliath — hand-picked by the Packard Motor Company to drive one of the companies newest, sleekly-outfitted, mountain-ready cars from San Francisco to New York as a savvy marketing scheme. Packard had been planning this trip for three months, and it showed in their progress — 10 days into the trip, they had already made it halfway across Nevada (ed. a trip that now takes around 10 hours). Jackson and the Vermont, on the other hand, had been forced to travel hundreds of miles north to circumvent the entire state when the Winton couldn’t handle the choking desert sandsand. But when halfway through Wyoming, they caught wind that their journey had turned into a race, Jackson remained optimistic.


But after 42 days on the road — almost half of the 90 he’d bet on — Jackson was only a third of the way to New York. Shortly after July 4th, the Packard car, despite having left a month after Jackson, was only 10 days behind them on the road. And on July 6, yet another car set out from San Francisco, this time backed by Oldsmobile. The stakes were even higher — these men carried a letter from the mayor of San Francisco to the mayor of New York, and were each promised $1,000 bonuses if they delivered it. Things were looking grim. 

But as Jackson crawled east, the roads were getting better. Gone were the alkali deserts and the uncharted, sage-filled landscapes. They were getting incredible amounts of rain, yes, but on one landmark day in Nebraska the Vermont was able to cover 256 miles. And it seemed the long, wide middle stretch of the United States was finally getting the better of the Packard and Oldsmobile expeditions — the duos were plagued by breakdowns, bad weather, and the sheer height of the Rockies. 

By the time the Vermont had made it to Chicago, the nationwide exuberance for these “continent-trotters” spurred the Winton Company into action. When Jackson arrived in Omaha, a Winton representative was waiting for him and offered Jackson the same financial backing and equipment as the Packard and Oldsmobile trips had. Jackson refused. They’d made it this far on their own, Jackson said. Why not try their hands at the rest of it? 


Cleveland to New York was the final leg of their journey. And — despite the one and only true crash of the entire trip — it went incredibly smoothly. At 4:30 am on July 26, Jackson and the Vermont crossed the Harlem River into Manhattan, officially rolling into the history books as the first men to drive an automobile across the United States. All it took was 63 days, 12 hours, and 30 minutes; 20 pounds off Jackson’s frame; and $8,000 dollars of his own money to win a $50 bet that he would never see through to collect.

In 1903, the Trans-Siberian Railroad was completed. Roosevelt telegraphed the first message sent around the world. A man drove the first motorcycle across the country, bumping along the railroad tracks heading east. The Wright Brothers flew their plane across the beaches of Kitty Hawk, NC. And with much thanks to Jackson, there began to be a push for better nationwide roads — byways that would ultimately let people travel when and where they wanted. 


In 1904, an automobile drove across the continent in half the time it took Jackson. In 1905, that time was cut in half again. In 1913, the Lincoln Highway was the first road to connect the east and the west, and in 1916, a car charged along its length in five days.

These days, Interstate 80 stretches for almost 3,000 miles from California to New Jersey. If you were to drive an average speed of 70 miles per hour along I-80 — hardly an outlandish thing to imagine these days —  it would take you less than 42 hours to drive from coast to coast. Even rounding up to three days, that's one-thirtieth the time Jackson was bet he couldn't make it in. How the times have changed. [H]

Liv Combe has yet to drive from San Francisco to New York, but it's on her list.
She's an Editor at Huckberry in San Francisco.
Follow her on Twitter and Instagram.

Images © Alex Souza

Images taken of Horatio's Drive: The First American Road Trip