In this episode of Stuff You Should Know, the hosts explore Horatio Nelson Jackson's 1903 cross-country automobile journey, a trip that demonstrated the potential of cars as viable long-distance transportation at a time when such travel seemed impossible. The episode details the state of American roads and transportation in the early 1900s, when horses vastly outnumbered automobiles and only 150 miles of America's 2.3 million miles of roads were paved.
The discussion covers Jackson's spontaneous $50 wager, his decision to purchase a 1903 Winton touring car, and his recruitment of mechanic Sewell Crocker. The episode examines the numerous technical and environmental challenges they faced, from constant tire failures to treacherous mountain roads, as well as the key figures who supported the journey, including Jackson's wife and Bud, the pit bull mascot. The hosts also touch on the trip's lasting impact and Jackson's later life accomplishments.

Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.
In the early 1900s, America's transportation landscape made long-distance automobile travel seem virtually impossible. The transcontinental railroad, completed in 1869, dominated long-distance travel, while horses remained the primary means of local transportation. With about 14 million horses compared to only 8,000 cars, automobiles were viewed as expensive toys for the wealthy, with the cheapest car costing more than the average American's annual income.
Of America's 2.3 million miles of roads, only 150 miles were paved, confined to major cities. The remaining roads were rough, rutted, and often impassable, especially west of the Mississippi. Navigation relied on inconsistent local knowledge and landmark-based directions, with no standardized road names or route numbers. The novelty of automobiles was so great that locals sometimes misdirected travelers just so their families could witness the rare sight of a car—one woman deliberately sent early motorists down a dead-end road to her family's farm for this very purpose.
Horatio Nelson Jackson, a retired doctor, made a spontaneous $50 wager at San Francisco's University Club that he could drive across the United States in under 90 days. With only four days of planning, Jackson assembled his expedition, recruiting Sewell Crocker, a talented 22-year-old mechanic whose skills would prove essential throughout the journey. On Crocker's recommendation, Jackson purchased a used 1903 Winton touring car for $3,000—equivalent to nearly $100,000 today—and named it Vermont.
The Winton was an open-air vehicle with no roof, windshield, or doors, featuring a two-cylinder engine with 20 horsepower, roughly equivalent to a modern riding lawn mower. A crucial decision in their success was choosing the northern route through Oregon rather than the more direct Nevada desert, which had defeated previous attempts. Though this detour added hundreds of miles, it provided more manageable terrain, including wagon trails and railroad right-of-ways that offered reliable, if still precarious, paths.
The journey faced countless technical and environmental challenges. Tire failures were persistent and major, with blowouts happening constantly despite stockpiling every available spare tire tube. The clutch repeatedly failed under strain from steep grades and rough terrain, requiring Crocker's mechanical expertise to keep them moving. Jackson and Crocker frequently became stuck—sometimes 18 times in a single day—using block and tackle to haul Vermont out of mud holes, riverbeds, and ditches. The vehicle's inadequate rubber brakes posed particular danger on steep, narrow mountain roads with cliff edges, while unreliable maps forced them to rely on directions from locals when navigating across unfamiliar landscapes.
Jackson's wife, Bertha "Swipes" Richardson-Wells, offered vital emotional support throughout the expedition, with their letters revealing deep affection and unwavering encouragement. Sewell Crocker received a substantial portion of the $8,000 Jackson spent on the journey—equivalent to roughly $267,000 today—reflecting the value placed on his crucial mechanical skills. In Caldwell, Idaho, the team was joined by Bud, a white pit bull who became a beloved mascot, riding between them while wearing custom "doggles" to protect his eyes from dust. Jackson adopted Bud for $15, and following the trip's completion, Bud lived out his days on Jackson's Burlington, Vermont farm.
Jackson's 63-day journey proved that cars could serve as viable long-distance transportation, defying prevailing beliefs about automobiles. Despite opportunities for lucrative sponsorships, Jackson turned them down to maintain the purity of his adventure, never even collecting on his original bet. Six years later, Alice Ramsey and three women completed the same route in 59 days driving a Maxwell Briscoe, proving both the viability of long-distance travel and women's capabilities under challenging circumstances.
Jackson went on to run multiple businesses, served as a decorated World War I officer in his 40s, and ran for governor of Vermont. He donated the Vermont and his driving goggles to the Smithsonian, ensuring that the story of his groundbreaking journey would remain accessible for future generations as a symbol of the transformative moment when automobiles proved themselves as practical tools for adventure and progress in American life.
1-Page Summary
In the early 1900s, America confronted significant challenges in transforming its transportation landscape. The nation was dominated by trains and horses, with automobiles a rare and impractical luxury. The state of the roads, lack of infrastructure, and primitive navigation systems made long journeys by car virtually impossible, highlighting just how audacious any attempt at cross-country automobile travel would have seemed.
The completion of the first transcontinental railroad in 1869, and the first cross-country train trip in 1876, solidified rail as the primary mode of long-distance travel for Americans. Even 25 years later, trains remained the default for anyone undertaking significant travel. For local movement within towns and communities, horses—sometimes with buggies, carriages, or stagecoaches—served as the principal means of transportation. There were about 14 million horses in the United States, compared to only around 8,000 cars.
Most Americans rarely ventured more than a dozen miles from their homes, often staying within just a few miles of where they lived. Cars were new, expensive, and regarded largely as toys for the wealthy. The cheapest car cost more than what the average American earned in a year. This exclusivity led to widespread skepticism about cars as a viable means of transportation, with a prevailing belief that trains and horses would remain dominant and that "cars will never amount to anything."
Of the 2.3 million miles of roads in the United States around 1900, only 150 miles were paved, and these were confined to major cities. The rest of the roads were rough, rutted, dusty, or muddy, and often in such poor condition that even walking them could be a challenge, let alone driving an early automobile. The roads west of the Mississippi were particularly primitive, further complicating overland travel.
East of the Mississippi River, rudimentary maps and guidebooks were available. These offered directions based on prominent local landmarks since there were no road names or route numbers; instructions might read “turn right at the old stone horse trough. ...
Early 1900s America: Roads, Infrastructure, and why This Journey Seemed Impossible
Horatio Nelson Jackson, a retired doctor, makes a spontaneous $50 wager at San Francisco's University Club that he can drive across the United States from San Francisco to New York in less than 90 days. At the time, this was about $1,500 in today’s money. With only four days of planning and preparation, Jackson assembles his expedition, lacking even a suitable car at the outset.
Jackson, already an enthusiastic car collector, is not driven by a desire for publicity or corporate recognition. Unlike contemporaneous efforts by major car manufacturers such as Packard and Oldsmobile, which were corporate-backed with advance supplies and teams of mechanics, Jackson’s journey is entirely self-directed. He undertakes the challenge to defend the honor and potential of the automobile, embracing it as an adventure rather than an orchestrated marketing effort.
Jackson’s financial independence comes in part from his marriage to Bertha Richardson-Wells, whose wealthy New England family amassed a fortune from celery tonic compounds. This background gives him the resources and time required for such a daring feat.
Recognizing the technical challenges ahead, Jackson selects Sewell Crocker, a talented 22-year-old small engine mechanic, to be his traveling partner. Jackson is in his early thirties at the time. Crocker’s essential mechanical skills are crucial throughout the trek, solving a wide array of problems, from clutch issues to tire and engine repairs. On several occasions, Crocker must bike dozens of miles on borrowed bicycles to acquire gasoline or parts—since there are no established gas stations in most of the country, especially the West.
The partnership between Jackson and Crocker is marked by genuine mutual respect and affection. Despite the hardships, the pair endure their journey together without resentment over their respective roles, adapting to frequent setbacks with optimism and perseverance.
On Crocker’s recommendation, Jackson buys the best vehicle available: a used 1903 Winton touring car for $3,000—a price equivalent to nearly $100,000 today. He names the car Vermont, in honor of his and Bertha’s home state.
The Winton is an open-air vehicle offering no protection from the elements: it lacks a roof, windshield, doors, and back windshield. The two-cylinder, chain-drive engine has 20 horsepower—roughly equivalent to a modern riding lawn mower, such as a John Deere X300, which has about 22 horsepower. Comfort is minimal and the car’s maximum speed is 30 miles per hour, but actual travel is much slower due to challenging road conditions, frequent breakdowns, and long waits for repairs.
Traveling the nation in su ...
Horatio Nelson Jackson's 1903 Cross-Country Automobile Journey
The early cross-country automobile journey faced countless technical and environmental challenges. Horatio Jackson and Sewell Crocker encountered continual setbacks due to unreliable equipment, inhospitable terrain, and poor infrastructure.
Tires were a persistent and major issue throughout the journey. At the time, car tires were prone to frequent blowouts and punctures. Jackson and Crocker tried to prepare by stockpiling as many used tire tubes as towns could provide, buying up every available spare despite the secondhand quality. Nevertheless, blowouts happened constantly, often leaving them stranded. There was a scarcity of replacement parts in rural America, especially as few people had ever seen a car. This shortage forced Jackson and Crocker to rely heavily on local blacksmiths and mechanics, who often had little or no experience with motorized vehicles, to perform makeshift repairs that could keep them going until the next breakdown.
The terrain and road conditions took a severe toll on the vehicle’s clutch, which was not designed to handle steep grades and the rough, unpaved surfaces they encountered. The clutch failed repeatedly under the stress, frequently rendering the car inoperable. Sewell Crocker had to diagnose and fix clutch issues with only basic tools and parts, demonstrating essential mechanical skills without which the expedition would have failed. His ability to restore the clutch after repeated breakdowns was as crucial as the block and tackle they used to free the car from difficult spots.
Jackson and Crocker frequently became stuck—sometimes as many as 18 times in a single day—requiring the use of block and tackle to physically haul their car, the Vermont, out of mud holes, riverbeds, and ditches. Each extraction was an ordeal, and the process was made even more difficult because their gear and supplies were often unsecured, routinely shifting or falling off during these events. They regularly lost valuable equipment such as cooking utensils and eyeglasses along their route, usually without realizing until it was too late to recover them.
The expedition also contended with daunting mountains and hazardous terrain, most notably when traversing the Cascade Mountains. The primitive roads were often no wider than a single car and bordered by cliffs, making progress slow and dangerous.
Challenges and Obstacles: Mechanical Failures, Tires, Terrain, Navigation, Getting Stuck
Jackson’s wife, Bertha "Swipes" Richardson-Wells, played a crucial role in emotionally supporting her husband as he undertook the daring cross-country expedition. According to Chuck Bryant and the letters exchanged between them, their relationship was marked by deep affection and unwavering encouragement. Jackson affectionately referred to her as "Swipes" in his letters, signing off with sentiments like "Yours Forever Nelson" and "My Dearest Swipes," underscoring the strength of their bond and her belief in his capabilities. Bertha’s enthusiastic support extended to her willingness to celebrate his achievement in person; she planned to take a train to Burlington, Vermont to welcome Jackson home and join in commemorating the successful journey.
Sewell Crocker, Jackson's mechanic and traveling companion, was fairly compensated for his expertise and crucial role in keeping the vehicle operational throughout the journey. Of the $8,000 spent by Jackson on the trip—an amount equivalent to roughly $267,000 today—a significant sum covered Crocker’s wages. After accounting for hotels, food, supplies, repairs, and other expenses, Crocker’s pay reflected the value placed on his mechanical skills, ensuring his interests aligned fully with Jackson’s goal to successfully complete the expedition across the country.
During their trek through Caldwell, Idaho, Jackson and Crocker were joined by Bud, a white pit bull gifted to them as a mascot. Bud quickly became an essential part of the adventure, riding between them and captivating crowds wherever they traveled. To protect Bud’s eyes from dust and debris during open-air driving, the team outfitted him with custom “doggles,” a detail that made Bud even more endearing and memorable to onlookers. The spectacle ...
Key Figures: Jackson, Sewell Crocker, bud the Dog, and Their Relationships
Horatio Nelson Jackson’s 63-day transcontinental journey in an automobile showcased that cars could serve as viable long-distance transportation, defying the prevailing belief that trains or horses were the only practical means to travel across the country. As Jackson and his companion neared the end of their trip, the journey became smoother, especially after Omaha, as cities and better roads appeared more frequently. Railroad right of ways provided remarkably flat and usable routes. With these improvements, the team’s progress accelerated, generating significant press coverage and public fascination. As Jackson neared his destination, New York City, throngs of press, journalists, and automotive company representatives greeted him, further amplifying public interest in the potential of the automobile for mass transportation.
Despite opportunities for lucrative sponsorships, Jackson consistently turned them down, such as when the Winton car company offered to sponsor him in the latter part of the journey. He chose to continue with support from Packard and Oldsmobile and kept his adventure independent to maintain purity of purpose. Jackson’s satisfaction came not from any financial reward—he never collected on the original bet he made—but from proving the viability of automobiles and the achievement of his bold goal. This decision reflected his adventurous spirit and confidence in his accomplishment.
Six years after Jackson’s feat, Alice Ramsey and three women became the first all-female team to cross the country by automobile, this time in a Maxwell Briscoe car. Their 59-day journey faced roughly the same obstacles and road conditions as Jackson’s, relying on similar technology. The press covered their trip extensively, and their success offered tangible proof that long-distance automotive travel was not only feasible but accessible to women as well. Their expedition advanced the accep ...
Legacy and Impact: Validating Automobiles as Transportation and Inspiring Future Cross-Country Journeys
Download the Shortform Chrome extension for your browser
