Way back in 1903, cars were pretty new. The first practical gasoline powered car came along in 1885, and the first American manufacturer got going eleven years after that. At the turn of the century, fewer than one in 10,000 Americans owned a car. Horatio Nelson Jackson, a Vermont doctor, wasn’t one of them, although he did think that cars were a damn cool thing.

He and his wife Bertha (He called her Swipes for some unfathomable reason) were in San Francisco in 1903, preparing to return to Vermont. While hanging out in the club with some other gents, Jackson went against the grain and declared that the automobile would someday be far more than an expensive toy for the rich, and to prove it, he took a $50 bet that he could drive from San Francisco to New York City in less than three months.

I’m sure Swipes thwocked him with a rolled-up newspaper or something. Nevertheless, he sent her on back to Vermont by more conventional means (no, not an airplane — this was May, and Orville Wright didn’t crank the engine on the Wright Flyer I until December), while he hired a young mechanic named Sewall Crocker to take the trip with him and plunked down $3,000 for a slightly used 1903 Winton Touring Car that Crocker suggested would be best suited for the trip.

Alexander Winton, like the Wright brothers a former bicycle guy in Ohio, had launched the Winton Motor Carriage Company in 1897, leading to the first automobile dealership in America (HW Koler’s in Reading, Pennsylvania) and the first auto hauler to get the Wintons from Ohio to Pennsylvania. Winton even tried a cross-country trip of his own in 1901, but the desert sands of Nevada defeated him before he really got going.

Jackson decided to skip Nevada, plotting a route north through Oregon then roughly following the Oregon Trail across Idaho, Wyoming and Nebraska. Instead of heading to the OT’s starting point in Independence, Missouri, Jackson’s plan was to cross Iowa and Illinois to Chicago, then Indiana, Ohio and a corner of Pennsylvania into New York state.

Jackson and Crocker took only four days to prepare for their journey — including buying the car, which Jackson named the Vermont after his home state — and left San Francisco on May 23. They crossed the Harlem River into Manhattan 63 days, 12 hours and 30 minutes, 5,600 miles, 800 gallons of gas and $8,000 later at 4:30am on Sunday, July 26.

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Along the way, nearly every part of the Winton had to be replaced, at times causing lengthy delays while they waited for replacement parts or hired a blacksmith to weld parts back together. The tires were the first to go, understandable, really — paved roads were practically unheard of in the West, and barely heard of in the East, and old wagon trails aren’t the easiest on inflated tires. At times, Crocker and Jackson wrapped rope around their wheels to keep the car moving.

Early on, they lost their cooking equipment, which bounced off as they drove, the noise from the car and the road hiding the sound of pots and pans crashing on the road behind them. They didn’t notice, either, when Jackson’s coat — with all their money in the pockets — flew off the vehicle. Fortunately, Swipes was a wealthy woman who wired them money to continue the trip.

While still in California, they stopped to ask for directions. I’ll let Jackson tell you the story, in a letter to his wife on May 25:

We met a red-haired young woman riding along on a white horse.

“Which way to Marysville?” I asked her.

“Right down that road,” she said and pointed. We took that road for … miles and then it came to a dead end at an isolated farmhouse. The family all turned out to stare at us and told us we’d have to go back.

We went back, and met the red-haired young woman again.

“Why did you send us way down there?” I asked her.

“I wanted paw and maw and my husband to see you,” she said. “They’ve never seen an automobile.”

In Idaho, they acquired a dog. From Jackson’s June 12 letter to his wife:

We left Caldwell at eight o’clock and after running a few miles out of town I found that I had forgotten my coat. On our way back we were stopped by a man and asked if I didn’t want a dog for a mascot. As I had been trying to steal one we were glad to get him so accepted the present (consideration $15.00). So Bud is now with us. 

Bud's goggles
Bud’s goggles

Before long, they were causing quite a sensation, and folks came out to greet them as the journey progressed. Bud was becoming quite the star too, especially in the goggles Jackson and Crocker had fashioned for him after noticing that the dust was as bad for him as it was for them, what with no windshield on the car. Bud even took in some sightseeing in Chicago, running off and delaying the start of the next leg of the trip while his drivers searched for him.

They also had a single-car accident near Buffalo, New York, that tossed all three of the travelers out of the vehicle but did no serious damage. That was on July 21. Five days later, the country’s first cross-country road trip was officially over, nearly a full month under the time Jackson had bet he could beat. He never collected on the bet, but returned home to his medical practice and wife in Vermont with Bud the dog. Much later, Ken Burns made a movie about it, Horatio’s Drive, and the Travel Channel’s “Mysteries at the Museum” did a segment on it:

Jackson’s Winton is now on display at the Smithsonian National Museum of American History, where he donated it in 1944, in a tableaux that shows Crocker using a block and tackle to pull the Vermont out of the mud while Jackson and Bud wait. It’s in much better shape now than it was at the end of the journey.

A hundred years after that first road trip, retired orthodontist and antique auto enthusiast Peter Kesler, with Alexander Winton’s great-grandson Charlie Wake along as his mechanic, duplicated the feat in another 1903 Winton Touring Car. There were almost as many mishaps as the Jackson/Crocker/Bud trip but less mud, hotels every night and no dog.

Oh, and just so you know, in 1909, a 22-year-old woman named Alice Huyler Ramsey and three other women made the New York to San Francisco trip in a green Maxwell 30 in 59 days using the route that later became the Lincoln Highway. Their trip, the first cross-country road-trip by women, was no less eventful than the Jackson, Crocker and Bud journey six years earlier. “They thought I was crazy,” she wrote in her 1961 book about the trip, Veil, Duster and Tire Iron. She drove across Nevada.

And yes, 100 years after Ramsey’s trip, someone repeated it, also in a green Maxwell 30. Her name was Emily Anderson.

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  1. Good read.

  2. Good read.

  3. Good read.

  4. Interesting.

  5. Interesting.

  6. Interesting.

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