First person who ever drove across the entire US did it for a $50 bar bet and it took him 2 months with most of his car needing to be replaced
Published on Mar 28, 2026 at 4:10 PM (UTC+4)
by Molly Davidson
Last updated on Mar 26, 2026 at 7:10 PM (UTC+4)
Edited by
Amelia Jean Hershman-Jones
In a time before freeways, highways, or any real roads between cities, the first person who ever drove across the US, Horatio Nelson Jackson, did it because of a $50 bar bet.
It started as a simple argument about whether or not it could even be done.
After all, in 1903, that meant crossing a country with almost no roads to follow.
And it ended up taking more than two months to pull off.
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Horatio Nelson Jackson drove across the US for a bet
Horatio Nelson Jackson was a doctor, not a driver.
But when he heard someone say cars couldn’t cross the US, he bet $50 that they could and then went to prove it.
So he set off from San Francisco in 1903 in a basic early car he later named ‘The Vermont,’ bringing mechanic Sewall Crocker with him.
At the time, there were no proper roads between cities, so most of the trip came down to guesswork.
For that reason, things started breaking almost immediately.
The car constantly needed repairs, which meant stopping in town after town just to keep going.
And since there weren’t proper mechanics around, blacksmiths ended up handling most of the fixes.
Along the way, they hauled the car over rough ground, dragged it through sand, and tried to navigate without reliable maps.
At one point, they were even close to running out of food.
After more than two months of breakdowns and detours, they finally made it to the East Coast.
But as they pulled into Vermont, the drive chain snapped.
The trip ended up costing far more than the bet was ever worth
In the end, that $50 bet was the cheapest part of the entire journey.
Jackson had spent thousands funding everything himself, even turning down an offer from the car’s manufacturer to sponsor the trip.
Instead, he wanted to prove it could be done on his own terms.
As a result, most of the car had been repaired, replaced, or rebuilt along the way.
Even so, the point wasn’t the money.
It was proving that cars could actually cross the country at all.
At a time when trains were still the only reliable way to travel long distances, that mattered.
Horatio Nelson Jackson never collected the $50 after he drove across the US.
By then, the bet was the least important part of the whole thing.
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With roles at TEXT Journal, Bowen Street Press, Onya Magazine, and Swine Magazine on her CV, Molly joined Supercar Blondie in June 2025 as a Junior Content Writer. Having experience across copyediting, proofreading, reference checking, and production, she brings accuracy, clarity, and audience focus to her stories spanning automotive, tech, and lifestyle news.
