Selects: The First Road Trip
Episode of Stuff You Should Know · July 11, 2026 · 50 min
Josh Clark and Chuck Bryant recount Horatio Nelson Jackson's 1903 drive from San Francisco to New York, the first cross-country automobile trip in America.
Summary
In this rerun of a 2023 Stuff You Should Know episode, Josh Clark and Chuck Bryant told the story of the first transcontinental automobile trip in the United States, drawing heavily on Ken Burns's PBS documentary Horatio's Drive and Dayton Duncan's book. They set the context of 1903 America: roughly 2.3 million miles of roads with only about 150 paved, some 14 million horses to 8,000 cars, no road names or route numbers, and widespread skepticism that cars would last. They described earlier failed attempts by John and Louise Davis in a Duryea and by carmaker Alexander Winton, who got stuck in Nevada sand.
The hosts recounted how physician Horatio Nelson Jackson made a $50 bet at San Francisco's University Club that he could cross the country in under 90 days, then set out four days later with mechanic Sewell Crocker in a used Winton touring car he named the Vermont. Bryant argued that the decision to route north through Oregon to avoid the Nevada desert was what ultimately made the trip succeed. They covered the pair's lost gear, blown tires, broken clutches, block-and-tackle extractions, misleading directions from locals, and competing, corporate-backed Packard and Oldsmobile teams.
The story's turning point for publicity came in Caldwell, Idaho, when a pit bull named Bud joined the trip and wore goggles. Jackson declined Winton's offer of sponsorship in Cleveland, survived an ejection crash near Buffalo, and arrived in Manhattan on July 26, 1903, after 63 days, 12 hours and 30 minutes; he never collected on the bet. The hosts closed with the later lives of Jackson, Crocker and Bud, Alice Ramsey's 1909 all-female crossing, Erwin "Cannonball" Baker's record, a digression on the death of Segway owner Jimmy Heselden, and a listener letter about the Amazon River's discharge.
Chapters
- 1:48
Introduction and sources
Josh introduces the Select rerun and the hosts credit Ken Burns's documentary Horatio's Drive and Dayton Duncan's book.
- 5:04
America's roads and travel in 1903
The hosts describe unpaved roads, horse-dominated travel, unmapped routes, and skepticism about cars.
- 11:35
Earlier failed attempts
The Davises' Duryea trip and Alexander Winton's attempt, which ended in Nevada sand, are recounted.
- 15:10
Jackson's bet and the Winton car
Horatio Nelson Jackson wagers he can cross the country in 90 days, recruits Sewell Crocker, and buys a used Winton touring car.
- 25:10
Setting out and early hardships
The hosts contrast Jackson's unsupported trip with sponsored Packard and Oldsmobile teams and describe gear, route choices and railroad driving.
- 32:23
Through the mountains
The departure from San Francisco, tire troubles, mountain roads, misleading locals, and constant repairs are described.
- 43:46
Segway and Fabio digression
Josh confirms that Segway owner Jimmy Heselden died riding off a cliff, and Chuck recounts Fabio's roller coaster duck strike.
- 47:21
Bud the dog joins
A goggle-wearing pit bull named Bud joins in Idaho and draws press attention as the trip eases east of the mountains.
- 50:41
Cleveland, Buffalo and arrival in New York
Jackson turns down Winton sponsorship, survives a crash near Buffalo, and reaches Manhattan after 63 days.
- 53:03
Aftermath and later records
The hosts cover the later lives of Jackson, Crocker and Bud, Alice Ramsey's trip, and Cannonball Baker's record.
- 57:06
Listener mail
Chuck reads a listener letter about the volume of water flowing out of the Amazon River.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Josh Clark
Clark stated that around 1900 the United States had 2.3 million miles of roads, of which only 150 miles were paved, all within big cities.
“the United States had 2.3 million miles of roads. Sounds like a lot. Pretty impressive. Yeah. 150 miles were paved”
Listen from 7:01 · Roads in the United States in the early 20th century
- Chuck Bryant
Bryant said there were about 14 million horses to roughly 8,000 cars in the United States at the time.
“about 14 million horses in the United States to about 8,000 cars”
Listen from 7:35 · Roads in the United States in the early 20th century
Linked moment · 12:39Skip to 12:39 using a listen link in the info box.
Chuck BryantBryant recounted that the 1899 Davis attempt failed publicly when a one-armed bicyclist given a 10-day head start beat them to Syracuse.
“they got beaten to Syracuse by a one-armed bicyclist who gave them a 10-day head start”
- Josh Clark
Clark explained that Jackson bet $50, roughly $1,500 today, that he could drive from San Francisco to New York in 90 days or less, and set out four days later.
“he slapped down a $50 wager that he could make it across the United States from San Francisco to New York in less than 90 days”
Listen from 15:53 · Horatio Nelson Jackson's 1903 transcontinental drive
- Josh Clark
Clark suggested Crocker recommended a Winton because Winton had already shown confidence in its cars by attempting a cross-country drive in one.
“Winton had already shown that they were making really good cars enough so that they were willing to try to make it a cross-country in one of them”
- Josh Clark
Clark compared the Winton's 20-horsepower two-cylinder engine to a modern John Deere riding mower with 22 horsepower.
“the two-cylinder chain drive engine had 20 horsepower. And my friend, a John Deere X300 series riding mower has 22 horsepower”
- Chuck Bryant
Bryant emphasized that Jackson's trip was unsponsored and assembled in four days, in contrast to corporate teams with advance supplies and mechanics.
“He put this together in four days, including buying the car”
Listen from 25:48 · Horatio Nelson Jackson's 1903 transcontinental drive
- Chuck Bryant
Bryant argued that routing north through Oregon to avoid the Nevada desert was the decision that ultimately made the trip successful.
“avoiding that desert, I think, is what ultimately made them successful”
Listen from 30:20 · Horatio Nelson Jackson's 1903 transcontinental drive
- Josh Clark
Clark called Stand by Me Rob Reiner's masterpiece and said it was far better than he remembered from childhood.
“that was a masterpiece. Like, that is Rob Reiner's masterpiece”
- Chuck Bryant
Bryant said the pair once had to use the block and tackle 18 times in a single day to pull themselves out of ditches, rivers or mud.
“I think the record was 18 times in a day. They had to use that block and tackle”
Listen from 34:59 · Horatio Nelson Jackson's 1903 transcontinental drive
- Josh Clark
Clark recounted that a woman on horseback deliberately sent them down a dead end to her family's farm so her relatives could see a car.
“a woman on horseback, who told them to get to the next town they should go down this road. And it dead-ended in her family's farm”
Listen from 35:39 · Horatio Nelson Jackson's 1903 transcontinental drive
- Josh Clark
Clark said Jackson spent about $8,000 on the trip in 1903, including Crocker's pay, which he equated to $267,000 today.
“It was about $8,000 back in 1903, which is $267,000 today”
Listen from 46:27 · Horatio Nelson Jackson's 1903 transcontinental drive
- Josh Clark
Clark said public interest in the trip surged when Bud joined, partly because of his goggles and his quick adaptation to riding in the car.
“When Bud joined it, people just went berserk over this whole thing. In part because he was wearing these goggles”
- Chuck Bryant
Bryant said Jackson turned down Winton's offer of sponsorship because he did not want the trip to become a corporate venture.
“I don't want this to become like a corporate sponsored thing. Like, we've made it this far. We can make it the rest of the way”
- Josh Clark
Clark said the trio reached Manhattan on July 26 after 63 days, 12 hours and 30 minutes, and Jackson never collected on his bet.
“63 days, 12 hours and 30 minutes after they set out from San Francisco, they made it to Manhattan, New York”
Listen from 52:34 · Horatio Nelson Jackson's 1903 transcontinental drive
- Chuck Bryant
Bryant noted that six years later Alice Ramsey and three friends became the first women to make the crossing, taking 59 days with Maxwell-Briscoe sponsorship.
“a woman named Alice Ramsey and three of her friends became the first woman and women to accomplish this same thing”
Listen from 55:01 · Alice Ramsey's 1909 transcontinental drive
People
In the conversation
- Josh ClarkCo-host of Stuff You Should Know
- Chuck BryantCo-host of Stuff You Should Know
Discussed
- Horatio Nelson JacksonAmerican physician who made the first cross-country automobile trip in 1903
- Sewell CrockerMechanic who accompanied Jackson on the 1903 drive
- Alexander WintonAmerican carmaker who attempted a cross-country drive in 1901
- Ken BurnsAmerican documentary filmmaker
- Dayton DuncanAuthor and documentary writer who wrote a book on Jackson's drive
- Tom HanksAmerican actor, director and producer
- Keith DavidAmerican actor who narrated Horatio's Drive
- Bertha Richardson WellsJackson's wife, from a wealthy Vermont family
- Rob ReinerFilm director allegedly killed by his son
- Wil WheatonActor who called Dwayne Johnson a coward
- Jimmy HeseldenBritish businessman and Segway company owner who died riding a Segway off a cliff
- FabioItalian-American model who was struck by a bird on a roller coaster
- Alice RamseyFirst woman to drive across the United States, in 1909
- Erwin "Cannonball" BakerAmerican driver who set a long-standing cross-country driving record
- Tom FetchDriver of the Packard team's 1903 cross-country car
Topics
- Horatio Nelson Jackson's 1903 transcontinental drive
- Horatio's Drive
- Winton Motor Carriage Company
- Bud (dog)
- Roads in the United States in the early 20th century
- Packard
- Duryea Motor Wagon Company
- Stand by Me (film)
- Segway
- Alice Ramsey's 1909 transcontinental drive
- Cannonball Baker Sea-To-Shining-Sea Memorial Trophy Dash
- Amazon River
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From the publisher
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. See omnystudio.com/listener for privacy information.
Summary, chapters and key points were generated from the episode transcript on September 30, 2026. Quotes are checked word for word against the transcript.