Jackson and his mechanic, a bicycle repairman named Sewell Crocker, stopped to ask a young red-haired woman for directions to Marysville, Calif. She pointed to a road that ran for about 50 miles and then dead-ended in front of a small farmhouse.
The farm family all came out to stare, then told Jackson he was headed in the wrong direction and would have to turn back. He did, and ran into the same young woman again.
"Why did you send us way out there?" Jackson recalled asking, in a letter to his wife.
"I wanted paw and maw and my husband to see you," the red-haired woman said. "They've never seen an automobile."
"And that," joked writer Dayton Duncan at a news conference for "Horatio's Drive," a new film about this 100-year-old road trip, "may have been the historical moment when American male drivers stopped asking for directions."
"Horatio's Drive," which premieres Oct. 6 on PBS, is the latest slice of Americana from documentary film director Ken Burns. The film was written and co-produced by Duncan, who also worked with Burns on PBS's 1997 "Lewis and Clark" and last year's "Mark Twain."
Jackson was a wealthy, 31-year-old retired doctor -- he'd given up his practice after a mild case of tuberculosis -- when he fell into a debate about automobile travel at San Francisco's University Club.
The other men in the room scoffed at the notion that the car would ever overtake the horse, insisting that it was merely "an unreliable novelty, a passing mechanical fancy," as Jackson later recalled.
On a whim similar to Jules Verne's fictional one in "Around the World In 80 Days," Jackson put $50 on the table and bet that he could cross the country by car in less than three months.
"I felt the story was wonderful," recalled Burns, who'd been hearing about the historic drive from Duncan, his longtime collaborator, for about a dozen years, "but it hadn't yet come together."
It finally did after the hundreds of calls that Duncan and his wife Dianne (both are former journalists) made to funeral homes and genealogical societies paid off.
They found Jackson's grandddaughters, who agreed to be in the film and share the letters and telegrams the adventurous young doctor had sent to his wife while making the trip.
"At that moment," said Burns, "we had a film." Especially when Tom Hanks, an admirer of Burns and his documentaries, agreed to read the part of Jackson.
"We figured we were dealing with this indomitable optimist, this Teddy Roosevelt, this American Everyman," said Burns, "and who better than Tom Hanks to personify that?"
As Duncan describes Jackson's trip in the film: "This is the story of a whim -- an individual who says, 'I wanna do it.'" And indeed it is the archetypical American story: Huck Finn lighting out for the territories, although in the opposite direction.
Jackson, who was just the third person to even attempt a cross-country drive, paid $3,000 ($500 more than the list price) for a cherry red 1903 Winton Touring Car to a Wells Fargo banker who'd already put 1,000 miles on it.
This at a time when $500 was the average annual wage. The Winton had a two-cylinder, 20-horsepower engine.
"I have a lawnmower at home that has about that much horsepower," Duncan noted. "The car was capable of speeds -- on a nice road, flat surface -- of 35 miles per hour, but if they were lucky they might have averaged 15 miles an hour."
Most days were not lucky. Blown tires, broken springs, snapped-off stud bolts, cracked axles were common.
When the Winton broke down in desolate southeastern Oregon --an area still so unpopulated that a group of 1990 census takers suffering mechanical problems were missing for four days -- it had to be towed to a ranch by a passing cowboy with his horse and lasso.
Jackson had detoured north from San Francisco through Oregon to avoid the Great Basin's sandy wastes. Two years earlier the car's manufacturer, Alexander Winton, had also tried driving from San Francisco to the East Coast as a publicity stunt.
But as soon as Winton got over the Sierras, Burns noted, "he got stuck in the deserts of Nevada and instantly called the thing off."
No wonder the car's sales brochure suggested drivers "maintain a cool head at all times, and master the interesting details of operation before venturing near brick walls and telegraph poles."
As one newspaper headline described Jackson's journey in a report about his arrival in town, the doctor "Declares His Trip Has Been Rather Expensive and Beset With Many Obstacles."
In Caldwell, Idaho, Jackson and Crocker acquired another traveling companion -- a bulldog named Bud, who quickly learned to wear driving goggles (the car lacked a windshield).
As Jackson put it in a letter, Bud was "the one member of our trio who used no profanity the entire trip."
Burns recalled talking about "Horatio's Drive" to a friend, who said, "Look, I'd make this film for one reason only ... the dog in goggles. That's it -- I'm watching."
"I don't know what it is about dogs," added Duncan, but they figure prominently in tales of American road trips from Lewis and Clark to John Steinbeck's "Travels With Charlie." Jackson's first letter home to his wife, in fact, mentioned he was looking for a dog.
"Somebody could get a doctorate degree writing about dogs and transcontinental journeys," Duncan said.
More central to the appeal of "Horatio's Drive" than its canine mascot, however, is the essentially American theme of the open road.
"Walt Whitman's greatest poem is 'Song of the Open Road,'" pointed out Duncan. "Willie Nelson's biggest song is 'On the Road Again,' and Bruce Springsteen's is 'Thunder Road.' It's not because these are all great works, but I think they're tapping into something that Americans in particular respond to."
"We actually invented a government that recognized, for the first time in history, no national religion," said Burns. "So we began to deal with the landscape in kind of religious terms: the Hudson River painting schools, the Transcendentialists."
"And the very nature of our government permitted individual citizens at all levels to move around," Burns added, "something that was not possible in any other culture, at any other time."
Besides all that, there's the irresistable romance of a man and his car. When it comes to the machine that's had the biggest effect on everyone's life in the past hundred years, said Burns, "it would be hard to argue anything more important that the autmobile."
The story of Horatio Jackson and his drive, Burns noted, is "a kind of snapshot of who we were at this incredible naïve and generous and guileless moment, before this unbelievable technology -- and all that this technology would bring -- changes us forever."
Jackson himself, Burns added, "is this irrepressible, wonderfully likeable guy at the turn of the century who embodies, I think, in many respsects, that moment."
On Aug. 7, 1903, Jackson arrived home in Burlington, Vt., 63 days after he set out from San Francisco. The trip cost him $8,000. He won that $50 bet, but never bothered collecting it.
Just as he drove into the garage, the car's drive chain -- one of the few parts that had never broken -- snapped in two.
Many years later, Jackson took his granddaughters to see the original Winton. By then it was in the Smithsonian, where it remains today.
The museum guard warned the girls they couldn't sit in the car. But, as one of the granddaughters recalled for Burns, Jackson told the guard, "I guess I can sit in the car if I drove it across the country."
"And," she added, "I'll always remember that."