Stuff You Should Know
Stuff You Should Know

Selects: The First Road Trip

July 11, 2026 • 49m

Summary

⏱️ 9 min read

Overview

In this episode, Josh and Chuck tell the remarkable story of Horatio Nelson Jackson, who in 1903 became the first person to drive across America in an automobile. What started as a $50 bar bet turned into a 63-day adventure across unmapped terrain, featuring mechanical failures, terrible roads, and a pit bull mascot named Bud. This is a feel-good story of optimism, determination, and the pioneering spirit that proved cars could be more than just expensive toys for the wealthy.

Setting the Scene: America Before the Interstate Highway

In 1903, America had 2.3 million miles of roads, but only 150 were paved, all within big cities. Cars were luxury items for the wealthy, costing more than the average American made in a year, with only 8,000 cars compared to 14 million horses. The infrastructure was built around trains for long-distance travel and horses for local transport, with most people never venturing more than 12 miles from home. Roads were unmapped, especially west of the Mississippi, and directions relied on landmarks like "turn right at the old stone horse trough."

  • In 1903, America had 2.3 million miles of roads but only 150 miles were paved, all in big cities
  • There were about 14 million horses in the United States compared to only 8,000 cars
  • The cheapest car would cost more than the average American made in a year
  • People generally didn't travel more than 12 miles from their house
  • East of the Mississippi there were maps and guidebooks, but directions were based on landmarks rather than road names
" At the time it was still a two-day journey, basically, from New York to Philadelphia. By horse. "

Previous Failed Attempts to Cross America by Car

Before Jackson's successful journey, several attempts had failed spectacularly. In 1899, John and Louise Davis were sponsored by the National Motor Carriage Company but famously got beaten to Syracuse by a one-armed bicyclist who had a 10-day head start. In 1901, carmaker Alexander Winton attempted the journey with his publicist, smartly starting from west to east to tackle the hardest terrain first, but got trapped in a sand dune in Nevada. These failures only heightened the challenge that awaited Jackson.

  • In 1899, John and Louise Davis got beaten to Syracuse by a one-armed bicyclist who gave them a 10-day head start
  • Alexander Winton attempted the journey in 1901 with his publicist but got trapped in a Nevada sand dune
  • Winton smartly started from west to east to tackle difficult terrain while the car was brand new
  • Despite failures, these attempts helped publicize car brands and kept the challenge alive

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