Selects: The First Road Trip

July 11, 2026

AI Summary

5 min read

In 1903, a wealthy, tuberculosis-stricken doctor named Horatio Nelson Jackson was lounging at the University Club in San Francisco when a fellow member dismissed the automobile as a useless fad. To defend the car’s honor, Jackson slapped a $50 wager on the table—roughly $1,500 today—betting he could drive one of those useless machines from San Francisco to New York City in under 90 days. Four days later, with almost no planning, he set out to do exactly that. The result was the first successful cross-country automobile road trip in American history, a 63-day adventure that was equal parts misery and joy, and that ended with a pit bull in goggles riding shotgun.

The Impossible Landscape of 1903

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What you'll learn

1 (02:31) **The Story We're Here For** - Josh and Chuck introduce the first cross-country automobile road trip as a rare feel-good story with no villains.
2 (04:54) **America in 1903: No Roads, No Maps, No Gas Stations** - The context that makes the trip seem nearly impossible: 2.3 million miles of roads, but all within cities; 14 million horses vs. 8,000 cars; most people never traveled more than 12 miles from home.
3 (11:26) **Previous Failures: The Duryea and Winton Attempts** - Two earlier sponsored attempts to cross the country by car, both of which failed, set the stage for Jackson's wager.
4 (15:16) **The Bet: $50 at the University Club** - Horatio Nelson Jackson, a wealthy retired doctor, bets fellow club members that he can drive from San Francisco to New York in under 90 days.
5 (17:33) **The Vermont: A $3,000 Used Winton** - Crocker advises Jackson to buy the best car available: a used 1903 Winton touring car, which Jackson names the Vermont.
6 (23:46) **The Race Against Packard and Oldsmobile** - Two months after Jackson left, Packard sent a fully sponsored team with pre-positioned gasoline; Oldsmobile followed a month later.
7 (30:57) **Departure and Immediate Trouble** - They set out on May 23, 1903, blew a tire within minutes, and the press barely noticed at first.

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Show Notes

Back when cars were a brand new thing, before people even knew they'd stick around, two men and a dog drove from San Francisco to New York. This classic episode has their story.

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