Stuff You Should Know

Podbit · Stuff You Should Know

Selects: The First Road Trip

Explore episode Jul 11, 2026

Where this was said

Crossing the Plains, Winton's Offer, and Cleveland

At 51:38 · chapter starts 49:00

By Wyoming, Jackson was writing home with confidence that they would make it. Once they reached Omaha, the trip shifted from ordeal to victory lap: flat plains, better roads, railroad right-of-ways they could cruise, and a steady march through Omaha, Chicago, Indianapolis, and Cleveland. On their best days they covered around 70 miles — not fast by modern standards, but impressive for a car with 20 horsepower on 1903 roads. In Cleveland, they passed through the home of the Winton Motor Carriage Company, whose founder had tried and failed at this same journey two years earlier. Winton, now aware that one of his own cars was close to completing the crossing, offered Jackson sponsored fuel drops and a technician escort for the home stretch. Jackson declined. He'd started this trip with no backing and he intended to finish it that way.

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