King Of The Road

More than a century after a Vermont doctor crossed the country over "ruts, bumps and thank-you-mams," memories of America's first road trip still linger on the nation's psyche

Story by Benjamin Pomerance

It really wasn't so different, that mother of all American road trips. There was adventure. There was booze. There was a dare that started it all. And there were plenty of the death-defying, teeth-gritting, knuckle-whitening, don't-tell-the-kids-you-did-this-when-you-were-their-age escapades now synonymous with the cross-country misadventures of America's wanderlust youth. Horatio Nelson Jackson did it in 1903. Adolescents with a few bucks in the glove compartment, responsibility in the rearview mirror and a makeshift sign reading "California or Bust" merely began doing it a few decades later. Otherwise, their stories merge as nicely as an entrance ramp with the interstate. There isn't a contrast to be found.

Except one. Jackson was first, America's original king of the road — or, at least, king of the road trip. At a time when the "horseless carriage" was nothing more than childish folly, the retired doctor from Burlington, VT, somehow managed to put the automobile on the map. He didn't mean to. All he wanted was $50 in cash and a lifetime of men's club bragging rights. Instead, he wound up with something greater, paving a road into the American psyche that has wound around potholes, roadblocks and speed bumps the size of Everest — and continues on today, greater and better than ever, with a story and a legacy that has lasted longer than the good doctor ever imagined it would.

"I think he knew his cross-country drive was important. But I don't think he ever would have predicted the degree of quality attention his story is receiving today."

Just ask Ann Wall. Growing up under the watchful eye of her daring Grandpa Jackson, Wall barely remembers the road trip being mentioned within the walls of their Burlington home. "The road trip was just something he did," Wall recalls. "And the way he was, when he did something, he did it as best he could, and then he moved on to a new great adventure. I think he knew his cross-country drive was important. But I don't think he ever would have predicted the degree of quality attention his story is receiving today."

Or ask Dayton Duncan. When it comes to preserving Jackson's legacy, few have done it better than Duncan, co-creator (with Ken Burns) of the PBS documentary Horatio's Drive and 18-year student of Jackson's travels. It was Duncan who, in 1990, pulled Jackson's trip out of the historical cobwebs, begged Burns to consider the story for a film, set out on a road trip of his own to follow the doctor's skid marks in a GM Suburban. "Horatio's drive by itself was not an event that so much changed history as reflected history," Duncan explains. "It signaled a new era in American history, heralding the true advent of the automobile age in our country. It was a more than deserving subject for a documentary."

Or even ask Peter Kesling, orthodontist by trade and vagabond by blood, the Indiana auto enthusiast who couldn't resist turning Jackson's road trip into a cross-country adventure of his own. "I didn't know anything about Horatio Nelson Jackson until I saw an old book called The Mad Doctor's Drive, or Sixty-three Days on a Winton Motor Carriage" Kesling says. "It sounded like me, so I got the book. That was where I first heard about Jackson. It piqued my curiosity, and I asked myself, ‘Could such a trip ever be done again?'" On the hundredth anniversary of Jackson's travels, Kesling sets out to find the answer.

Yet we're getting ahead of ourselves.  There's a bet to be won, a cross-country trip to make, a million surprises to be found on a road that winds through the century and connects the most unlikely companions imaginable in the same route. Like any good road trip, it isn't about the destination. It's about the journey. Let's get started.

It starts, as road trips do, in the bar. The year is 1903. The place is the University Club of San Francisco. The topic is cars. The tone is one of ridicule. Automobiles are too new, too dangerous, too expensive and too slow to ever catch on with the American people. They're a novelty now, laugh the rich men at the counter, but wait a few years and see what happens. We'll be back to horse travel in no time.

A man rises from the corner. It's Jackson, traveling through in San Francisco with his wife, chasing after one of his frequent strike-it-rich schemes. Not that he needs the extra cash. He's already married to one of the wealthiest heiresses in Vermont, allowing him to  retire early from his medical practice. He already owns a beautiful home, a stable of thoroughbreds, an island in the middle of Lake Champlain. What Jackson needs is adventure, and plenty of it. He's about to get more than he ever bargained for.

"My grandfather was someone who was always driven by a challenge"

"My grandfather was someone who was always driven by a challenge," Wall says of Jackson's impulsive personality. "Someone was always telling him, ‘No, you can't do that.' If somebody told him that, he was always quick to respond, ‘Yes, I can, and I will.'"

The men at the bar can't believe their ears. Jackson is actually arguing for the merits of the automobile. He suggests that cars not only will last a few years, but will become the main mode of transportation in America within a decade or two. Then he drops the hammer. A car, he says, can even carry a man across the country. 

"Everyone," Jackson later would recall, "pooh-poohed the idea of even attempting such a journey." The doctor persists in his claim. One of the men tries to call his bluff, throws down a $50 wager that nobody could drive from San Francisco to New York City in less than three months. Jackson takes the bet. He doesn't own a car and hasn't the foggiest idea how to drive one, but the die has been cast. Let the road trip begin.

"In a way, I wish I could've been there," Kesling says. "Can you imagine the faces of those people when he (Jackson) told them he was going to drive cross-country in one of those things?" He laughs. "Probably about the same reaction I got when I said I wanted to do the same thing."

Jackson's isn't about to let disapproving bystanders change his mind. He buys his first automobile, a bizarre-looking Winton touring car with a top speed of 30 miles per hour, for the shockingly high price of $3,000. He hires a mechanic, 22-year-old bicycle mechanic Sewall Crocker, after a one-candidate job search on the streets of San Francisco. With few maps, no experience, and only 150 miles of paved highways in the entire country, the doctor sets out to conquer the open road.

Twenty minutes later, the conquest comes to a halt — temporarily. It's a flat tire, a contingency Jackson has no idea how to overcome. Three blocks from their starting point, the road trip seems on the brink of a premature ending. Thankfully, his traveling companion has seen deflated wheels of rubber all the time in his bike shop. Before long, they're on the road again. The first day's misadventures have proven something to Jackson. Crossing the country in a car won't be as easy as it may have seemed.

"The road trip was really who my grandfather was"

"Whenever I hear about my grandfather on the trip, or read the letters he sent home to his wife, my grandmother, I can feel how much this meant to him," Wall says. "I can understand how many challenges he faced, and how proud he was when he overcame them. The road trip was really who my grandfather was."

Yet no amount of gumption and support could surmount the unavoidable delays of road travel in early-20th century America. Eleven days into the trip, he and Crocker are trapped at a stagecoach inn in Alturas, California, showing the Winton to slack-jawed bystanders and waiting for a shipment of new tires to arrive. For five days, the men wait.  Jackson, though battered, is hardly beaten. "Just as soon as we get good tires, we will make a record run," he writes in a letter to his wife. "I feel more confident that I can make New York." Sure enough, he makes a record drive after Crocker repairs the tires, going all the way to Lakeview, Oregon, on Day 12. Then comes another delay after the engine blows, three more days wasted, and even Jackson begins to wonder how he can ever make it across the continent. Worst of all, an enterprising Lakeview merchant charges him $3 for a gallon of gasoline, ten times the average price at the time. At this point in the journey, one can only imagine how far away New York must have seemed.

Not that the in-transit phases of the trip are much better. When the car actually works, most of the day is spent "bouncing over unmarked paths that were a compound of ruts, bumps and thank-you-mams." Writing home after a particularly rough day, Jackson describes the experience as "alternately working on the car, pulling it out of mud holes, teetering on the edges of cliffs or simply getting lost." On a particularly harrowing road in the Cascade Range, their mess kit bounces from the car and over a cliff, but Jackson and Crocker decide starvation is preferable over turning back. They press on. 

Then Jackson finds what he's looking for. It's not a paved highway or an accurate map or even a new car. It's a dog, the road trip mascot Jackson has craved. A light-colored bulldog, bought in Idaho, christened "Bud", and outfitted with a custom pair of goggles for the expedition. "He was," Jackson later recalled, "the only member of our trio who used no profanity on the entire trip." Perhaps he's a good-luck charm, too. The going's still slow, but Jackson and Crocker…and now Bud…start to pick up speed. On July 1, they cross the Wyoming border. Twenty-one days later, they're in Buffalo, New York. Incredibly, journey's end is in sight. 

"When he got close to the end, he must have been somewhere between exhausted and ecstatic," Kesling says. "I don't know, because I obviously wasn't there, but after what he went through, he must have felt like he'd conquered the world."  

On July 26, 1903, a banged-up Winton touring car containing Horatio Nelson Jackson, Sewall Crocker and Bud the bulldog arrives in New York City. They have made the trip in an astounding 63 days, well ahead of schedule and leaving behind, in Jackson's words, "a littering of broken parts, tools, flat tires, clothes and tears." After nearly three months of well-documented adventures, America's first road trip is over.

"As someone who's spend a lot of his adult life traveling across America in a car, it had a special appeal to me"

Wait. There's still a bit more gas in the car. Let's press on, all the way down a road that transfigures time and space, winding through the decades all the way to the year 1990 and a film studio door in Walpole, New Hampshire. Dayton Duncan stands at that door, trying to convince his friend Ken Burns to make a documentary out of some road trip that nobody's ever heard of. "It seemed to have great story potential," Duncan says of Jackson's trip, a vignette he learns by accident while doing research for another book. "As someone who's spend a lot of his adult life traveling across America in a car, it had a special appeal to me." Burns doesn't take the bait. No chance, he tells Duncan. Not for a story no one's ever heard of.

Burns isn't the only one to doubt the significance of Jackson's tale. Ann Wall recalls traveling with her family to Washington, D.C.'s Smithsonian Museum of American History to see the famous Winton, which her grandfather donated to the museum's collection after returning home from his trip. "When we got there, my grandfather wanted to inspect his car and see what they had done with it," Wall remembers. "And he actually went up and sat in the car. A security guard came running over and said, ‘Sir — you can't sit there.' And my grandfather, with a shower of expletives, looked the guard in the eye and told him ‘Well, I guess I can sit in it if I want. I drove it across the country.'" She laughs at the memory. "The guard didn't know what to do. Finally, he just walked away."

Like the Smithsonian security guard, Burns eventually gives in to Jackson's story. "It took me a decade to convince him," Duncan says. So the two traveling companions hit the road, Duncan and Burns replacing Jackson and Crocker in the driver's seat of America's first road trip. Like Jackson and Crocker, their voyage required some creative problem solving techniques. "Our intention from the start was to put the viewer in the front seat and see what Jackson saw," Duncan says. "So we put our cameraman, Allen Moore, on the front hood of the GM — strapped to a harness for safety — and had him film old wagon roads we discovered to give the sense of moving through space, just as Horatio would have experienced it."

Then came the triumph, two disparate roads merging into one. One evening, Wall's husband answered the phone to hear an unfamiliar voice at the other end of the line. It was Duncan's wife. After years of searching, she had finally located someone related to the subject of her husband's documentary. "Needless to say, we were amazed," Wall says. "We didn't really know, of course, that anyone was doing a film about my grandfather. The fact that Dayton had taken such an interest in his story was wonderful." The aura of amazement, Duncan says, was mutual — particularly when Wall agreed to give him the packet of letters Jackson had sent his wife during the road trip. "When I heard that," Duncan remembers, "I knew we could now tell Jackson's story with a greater degree of intimacy."

On the 100th anniversary of Jackson's trip, Florentine Films releases Horatio's Drive, the final fruit of Duncan's and Burns' labor. Neither man has any expectation for public acclaim. Both are wrong. The story of America's first road trip becomes a national sensation. "Ken and I are happy that so many other Americans saw in Horatio's story the same things we did: an interesting moment in American history, an indomitable character, and a rollicking take of a road trip," Duncan states. The documentary is a success, spurring an expedition by the Smithsonian Institution on American travel that features Jackson's story as the main attraction. The once-obscure story is now squarely in the national spotlight. 

"When you're lying in the hospital bed, and your wife says ‘You're not making the trip,' that's a bad sign"

And through a series of odd twists and turns, Horatio's drive finds its way to the doorstep of Peter Kesling. After reading the book about Jackson's trip, the 71-year-old Indiana orthodontist decides he has to try the impossible: recreating the doctor's journey 100 years later. He begins buying Winton automobile parts from around the country, assembling them into the same model of car Jackson drove on his now-famous voyage. Even a road test accident in 2002 which totals the car and send the orthodontist to the emergency room doesn't deter his adventurous spirit. "When you're lying in the hospital bed, and your wife says ‘You're not making the trip,' that's a bad sign," Kesling says. "But I got very stubborn, and decided nothing and nobody was going to stop me." He begins re-building the antique auto — and starts finalizing plans for the journey.

On June 17, 2003, two Winton touring cars depart from San Francisco: one driven by Kesling, the other piloted by Charlie Wake, great-grandson of the original Winton company owner. Much has changed in the 100 years since Jackson's journey — most notably, Kesling says, the rise of the tractor trailer. "Jackson had it easier," Kesling laughs. "There were hardly any other drivers on the road then. Now, you're going 30 miles per hour, and you've got an 18-wheeler bearing down on your back. It comes as a surprise when you realize how hard it is to handle one of those old cars."

Kesling says no surprise was greater than the one he had waiting for him in Bellevue, Ohio, a place where the byways of this century-long road trip ran together again. Pulling into town in the late afternoon, Kesling was shocked when a woman walks up to him and introduces herself as Ann Wall, granddaughter of the man who had inspired Kesling to make this incredible journey. "I almost fainted," Kesling remembers. "She was there with her son and his sons, and they climbed all over the car. We talked all about her grandfather. I feel as if I understand his trip better after talking to her." Along the way, Kesling also meets Duncan, who interviews him for Horatio's Drive. "That documentary is incredible," Kesling says of Duncan's creation. "That's the main reason why people are talking about Jackson today."

On July 27, 2003, 100 years to the day after Jackson arrived in New York, Kesling's Winton wheezes down 42nd Street to the delight of a cheering crowd, an automotive hero just as Jackson had been a century ago. Five years later, the orthodontist still savors the memories of his 3,720-mile odyssey. "I'd do it again," he says, a schoolboy's enthusiasm evident in his tone. "I'm still in pretty good shape." Yet the rigors of such a trip it is dangerous, a fact Kesling wholeheartedly acknowledges. "In Wyoming, a state trooper pulled us over for going too slow," Kesling says, "and he told me ‘I'm worried about your safety.' I told him, ‘Me too. But I'm not stopping now.'" He pauses. "And I'm glad I kept going."

"That's at the heart of every road trip, and it certainly is the heart of Horatio's drive."

The century-long road trip of Horatio Nelson Jackson is over. Yet the road continues on, twisting into infinity and gaining more traffic every time an American speaks those sacred words: "Let's take a road trip." The roads are paved, the cars are faster and goggle-wearing dogs rarely ride shotgun anymore, but the principle is the same. "We're a restless people for whom ‘freedom' is often equated with traveling across some portion of this immense and beautiful continent we inhabit," Duncan explains. "That's at the heart of every road trip, and it certainly is the heart of Horatio's drive."

Yet perhaps the most enduring testimonial of American road-tripping comes from the man who did it first. "I have had," Jackson told the press upon arriving in New York, "the finest adventure of my life." In the realm of road trips, one can't think of higher praise than that.

Have you ever heard of Horatio Nelson Jackson's cross-country drive?