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The Vermont: A True American Road Trip Story

The Vermont: A True American Road Trip Story


The Winton Motor Carriage

Ah, the good ‘ole Winton Motor Carriage. It was once one of few motorized carriages available to people willing to give up their actual horse and carriage for some manmade horse power. Established in 1896, the Winton Motor Carriage Company in Cleveland, Ohio, was a pioneer in the United States automobile manufacturing industry, straight from the mind of the Winton Bicycle Company owner, Scottish immigrant Alexander Winton. But, let’s go a little further in time, to another person in history, shall we? Say, Horatio Nelson Jackson in 1903?


Winton Motor Company Logo

Winton Motor Company Logo


The Young Physician

Young physician and auto enthusiast, Horatio Nelson Jackson had been practicing medicine in Brattleboro and Burlington, Vermont in the early 1900’s. Although Jackson had no mechanical experience he was an early automobile enthusiast and pioneer in his own right. During his time, the automobile was a new up-and-coming machine made available as a viable mode of transportation for man at that time; transportation that didn’t need rest, food, or water like its animal counterparts, the horse and mule. The automobile, given proper terrain, could also go where no one-dimensional mode of transportation (forward/backward), like the steam train, could go that was available to people at that time. With an automobile, the limits of transportation for man were stretched, expanded and made possible the two-dimensional mode of transportation (left, right, backward, and forward) as his trusty four-legged, muscle and tendon, warm blooded vehicle once was for him. The future had come for those who could afford the approximate $1000 expense in the late 19th and early 20th century.


Horatio Nelson Jackson

Horatio Nelson Jackson


The Fad

Back in those days, there was a collective agreement among most that the automobile was a fad, a growing craze of new machinery that would soon pass as a once recreational amusement device composed of cogwheels, steel, rubber, oil and gas. But, for Jackson, it was the vehicle that he knew would eventually allow for people to travel through great regions and distances, much further and faster than what people had imagined in those days for transportation. It seemed that he could see the bigger picture, that the automobile would be a device that could expand the imagination, fuel inspiration, and drive people to explore further than their own city, town, or county. Just imagine, a more efficient mode of transportation that could take you dozens of miles in a day, rather than a dozen miles in a day; one that you could take just about anywhere, whenever you wanted, without feeding it, watering it, or having to buy a ticket to leave on it at a time someone else scheduled for you. It was a machine that was starting to become an opportunity to not only save time for many, but also allow a freedom that many had never experienced before its existence.


The Winton Motor Carriage Newspaper Ad

The Winton Motor Carriage Newspaper Ad


The Wager

Back in 1903, on May the 18th, Jackson was at San Francisco’s University Club as a guest where he had ran himself into a little wager. $50 was on the line, for him to pull off a feat that hadn’t been successfully accomplished by any other man on the planet before him. You see, it seemed that Dr. Jackson was a risk taker and a great adventurous man in his day to have taken such a contract; for to have the gall to volunteer oneself to attempt a feat into an unknown adventure, takes great grit and courage, and maybe a dash of crazy. The wager was set for the 31-year-old Dr. Jackson to prove once and for all that an automobile could be driven clear across the country. There was just one problem though. Jackson didn’t own a car.

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The Plan

Not only did Jackson have no car to attempt this wager, but he practically had no experience whatsoever in driving an automobile either. He didn’t even have any maps that he could follow to help guide him for his quest; a tool we in the 21st century take for granted being in the age of cellular devices that are linked to satellites in low Earth orbit on the shore of space using quantum physics to guide our own routes via GPS devices and applications. How far we’ve come indeed, and how desperate many in our time would be if left without their modern devices to help guide them in their own excursions.

Still in San Francisco, Jackson, along with his wife, had planned to go back to their home in Burlington, Vermont, in just a few days. To attempt this bet they both took automobile driving lessons while in San Francisco in order to learn the basics of operating such machinery. When it was time to bite the bullet, Jackson’s wife returned home by train, leaving Jackson to attempt his cross country drive in an automobile alone.

The Companion

Since Jackson had no mechanical experience, he got wise and decided it best for him to try out his best sales pitch to attempt to persuade someone who was mechanically inclined to tag along with him in order to give him assistance if needed. Jackson was able to convince a young mechanic and chauffeur named Sewell Crocker, to serve as his travel companion, mechanic, and backup driver. 22-year-old Sewell was a bicycle racer from Tacoma, Washington. Sewell was also the fella who taught Dr. Jackson and his wife to drive.


For Hire

The Vermont

It was Sewell Crocker who suggested to Jackson that his first automobile purchase and cross country vehicle for his wager be a Winton. This is where the Vermont came into Jackson’s life. Jackson ended up buying a slightly used, two-cylinder, 20hp Winton. Being from Vermont, Jackson saw fit to name his steel ride the Vermont, in honor of his home state.

Jackson and Crocker left San Francisco on May 23rd, with the Vermont loaded with their road trip essentials. For their first ever cross-country road trip, they sure came prepared carrying items like coats, rubber protective suits, sleeping bags, blankets, canteens, a water bag, an axe, a shovel, a telescope, tools, spare parts, a block and tackle, cans for extra gasoline and oil, a Kodak camera, a rifle, a shotgun, and pistols.[1]

Before leaving, Jackson had recognized that he needed to plan which direction and route he would take for his cross-country feat. Alexander Winton, the owner of the company who manufactured Jackson’s car, the Vermont, had failed at an attempt to cross the desserts of Nevada and Utah. With this knowledge, Jackson had decided that a more northerly route, up through the Sacramento Valley and along the Oregon Trail would be a more successful path to take for his road trip and on May 23rd, 1903, the Vermont was transported on a ferry from San Francisco to Oakland, California, to start his cross-country road trip and to make his way toward the east.


Jackson driving his Winton (the Vermont)

Jackson driving his Winton (the Vermont)


The Road Trip

The time had come. Day 1 of Jackson’s cross-country road trip had begun out of Oakland. He had his Winston car named the Vermont, he had automobile driving practice, he had everything that he thought was necessary for his journey, and he had his companion, Sewell Crocker, also his mechanic who was there for any mishaps or mechanical failures the Vermont might run into. Just as you might expect, there were a few ordeals along the ride. Within 15 miles (24 km) of the start of their journey, the Vermont had a blowout on its rear tire. Luckily Crocker was there to help Jackson change it out with the spare they luckily had, because it was the only right-sized spare that could be found in all of San Francisco. Later that night, their first night, they realized that the side lanterns on the Vermont were inadequate and could not guide them well in the dark, so the next night they stopped in Sacramento to replace them with a spotlight they mounted on the front of the Vermont. While in Sacramento, Jackson and Crocker were assisted by some bicyclists who offered them road maps that were most likely greatly appreciated, since they started out their trip without any to guide them along their way.

Back in the day, cars were not quiet, humming machines like they are today. They were quite noisy, and driving on poor road conditions did not help with the noise level either. Most driving conditions were hard, unkempt terrain that would bump, bounce and toss, and vibrate the driver, any occupants, and items within the vehicle. Due to such racket, it made it nearly impossible for Jackson and Crocker to hear their cooking gear falling off the back end of the Vermont as they drove. On top of that, it didn’t help when they’d meet someone they’d hope to get honest assistance from, to only be misdirected off course. Yes, thanks to some woman they had encountered and asked directions for, she ended up leading them in a 108-mile (174 km) detour toward some relatives of hers, so that they could have their experience at witnessing a real life automobile for themselves, as she had done encountering the gentlemen.

The first leg of their trek led them northward out of Sacramento through the Sierra Nevadas where their Winton waded through streams and meandered along narrow mountain roads not made for automobiles. In order to proceed, Horatio and Sewell at times had to move boulders by hand. Other events delayed their drive, like a broken clutch and a clogged oil line. Yes, just as the first manned missions to go to the moon were struck by obstacles and hardships; attempts to trek across country in an automobile for the first few times in history had its own obstacles and hardships to overcome as well. Luckily though, back on Earth, Horatio and Sewell could find help if stranded, as they had to do when they found themselves stranded with their disabled car for eight hours in the Oregon desert. They received the help of a cowboy who used the help of his horse to tow the Vermont for repair. Back then, it wasn’t like it is today where you can just go down the road to an Advanced Auto Parts store to get the parts you need, or have Joe from Joe’s Mechanic Shop to tow you for service, or call AAA. They had to rely on stagecoaches to bring new parts and blacksmith’s to make repairs.[2]


There were times the men had to get innovative and many times where luck was on their side. If they blew tires, they’d get along by wrapping rope around the wheels in order to get somewhere they needed to acquire new tires. One time Jackson did find a telegraph office where he was able to wire back to San Francisco for replacement tires to be delivered to them along their journey. Another time, after a gas leak left their tank almost empty, Crocker set out on a 26-mile bicycle ride to the nearest town he came across. During this bike ride, Crocker’s bike got a flat tire (this was a common theme for their road trip) and had to walk most of the way back toting along a gas can full of fuel. It took Jackson and Crocker 19 days just to reach Idaho from their start, a drive that would take less than 24 hours today. In Idaho, they picked themselves up another companion, a four-legged one named Bud. Bud was a pit bull whom Jackson purchased for $15. They fitted Bud with his own motoring goggles in order to protect his eyes from all the dirt and dust the Vermont would kick up along the drive as he rode shotgun with the gentlemen. He seemed to wear them with pride now that he had his new owners.


Bud the pitbull

Bud with his motoring goggles on



As you can imagine, a physician, a bicycle racer and mechanic, and a pit bull named Bud who wore motoring goggles, all sitting in a double seat Winston named the Vermont packed with all their road trip essentials traveling across the country made quite the headlines for their day. It seemed the trio was becoming quite the celebrities and the newspaper reporters were coming out of the woodwork from all over to take their photograph and interview them. Oh, if Bud could talk! As they traveled through towns, curious onlookers crowded the car to see the automobile and its occupants. For many, it was their first time seeing an automobile in person. By the time Jackson and his road trip crew arrived in Omaha on July 12th, his bar bet was beginning to catch the attention of many and fascinate the nation.

After many mishaps, mechanical failures, delays, unwanted detours, and distractions, they finally started making good time once they became more adaptive in their journey and began averaging 150 miles a day. They arrived in Chicago on July 17th, where they were greeted warmly, and treated by city officials and automobile dealers with receptions. As you can imagine, an excursion such as theirs would have played in favor for the automobile industry in those early days, by catching the imagination of many across the nation and showing how others too would be able to take road trips for themselves if they were to own an automobile. On the 20th of July, a convoy greeted them just outside Cleveland to escort the Winton back to its manufacturing birthplace.

Throughout their entire road trip excursion Jackson, Crocker, and Bud had many triumphs and pitfalls, but only one accident which tossed all occupants out of the vehicle. But luckily all, including Bud and the Vermont, came out just fine with only dings, bumps and bruises. Although they gained quite the following throughout their entire road trip adventure, by the time they ended their epic travel and arrived at their destination, it was about as quiet as it was at their departure. On Sunday, July 26th, the cherry-red Vermont, covered in dirt and mud, crept into a deserted 5th Avenue in New York City’s Manhattan at 4:30am. Their entire road trip was approximated to be around 4500 miles that took them 63 days, 12 hours and 30 minutes to complete. At the end of it all, Jackson had won his $50 wager with nearly a month to spare. He may have won the wager, the spirit of many, and a great pride for achieving such a feat, but he lost around $8000, due to the expenses of keeping the Vermont, himself and his companions going.



The Threshold

After the excitement of the road trip was over, Jackson left Manhattan to go back to his wife in Vermont, driving the Vermont. About 15 miles outside his home the Vermont broke down on him again, and his two brothers, each driving his own automobile, had to tow him the rest of the way home. The Vermont wasn’t through yet, because once his brothers got back on the road they both broke down and Jackson used the Vermont to tow them both back to their homes. Finally, Jackson returned to his home for good with the Vermont and as soon as he entered the threshold of his garage the drive train snapped in two, right at the last moment of the Vermont’s run. The drive train was one of the few original parts never replaced during the Vermont’s entire journey.


Winton Motor Company Logo

Exhibit at the National Museum of History recreating H. Nelson Jackson's first successful North American transcontinental automobile trip in a 1903 Winton touring car, the Vermont



The story of Horatio Nelson Jackson and his Winton named Vermont is not only about a man and his car set out to prove a wager to be won. Jackson’s story began with his great enthusiasm as to what the automobile was, what it was becoming, and what he saw that it could be for people in the future. The automobile would become a device that would eventually give great freedom to millions, if not billions of people throughout the world for years to come. The automobile would become a freedom not only unique in the North America and Europe, but a freedom that would eventually be shared worldwide.

Recall your last road trip adventure. You may have set out on yours as a vacation to get away from the weekly grind of work and responsibilities. Remember how it felt to get away for a while was for you? Imagine what a feeling like that would have been to someone riding in a car for the first time, or for someone who had never seen one before during Jackson’s era. Automobiles practically didn’t exist for many back then. It must have been a feeling like the early European settlers felt leaving to America a century or two before Jackson’s time. There must have been a feeling of relief, a sense of adventure never experienced before, and a feeling of true God given freedom. So, don’t take for granted your ability to drive and experience freedom for yourself the way you are able to compared to those before you. If possible, take a wager on yourself and go out on a great road trip adventure to create your own story to be shared for the next century to come.

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Page References:

[1] https://en.wikipedia.org/wiki/Horatio_Nelson_Jackson

[2] https://www.history.com/news/the-first-great-american-road-trip

Dustin H.

Lover of road trips, married, a father, an entrepreneur, chaser of dreams.

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