Jackson's journey from San Francisco to New York City was by no means certain. He faced dirt roads, mountains, mud, breakdowns and mishaps along the way. Two years earlier, the automobile developer Alexander Winton had also attempted to drive across the country, but his car got stuck hopelessly in the sands of Nevada. Jackson learned from Winton's mistake, though, and decided to avoid Nevada completely, driving north to Oregon instead of following a more direct route. Otherwise, when he could, he stayed on roads near railroad tracks, sometimes crossing railroad bridges when there was no clear path.
There was a time before gas stations existed, so Jackson had to buy fuel from general stores that carried it for farm equipment.His Winton car only held about 12 gallons (45.4 liters) of fuel, so he packed extra. Without headlights, he affixed an acetylene lamp to the front of the car. And without reliable road signs, he had to trust local advice and made several wrong turns along the way. Boulders often blocked the road, and occasionally the car would get stuck in deep streams or mud, requiring Jackson and Crocker to pull it out with the block and tackle. Jackson lost several personal items along the bumpy roads, too, including cooking gear and two pairs of spectacles. More than once, he was held up for several days in towns waiting for shipments of replacement parts for the car.
On June 20, about a month into Jackson's journey, two men commissioned by the Packard Motor Company left San Francisco for a cross-country automobile publicity stunt. Unlike Jackson and Crocker, the company planned every step of the trip and sent along an expert machinist. Furthermore, another cross-country team driving an Oldsmobile set out on July 6. Jackson soon learned of the rival trips and was determined to finish before them. Indeed, had the Packard team not made a detour planned for publicity purposes, they would have beat Jackson to the New York City finish line. Eventually, the Winton Motor Carriage Company, which manufactured Jackson's car, learned of his expedition and offered to fund the remainder of the trip, but Jackson refused.
He made it to New York City in 63 days, beating all competitors. His route brought him from California through Oregon, Idaho, Wyoming, Nebraska, Iowa, Illinois, Indiana, Ohio, Pennsylvania and finally New York. His $50 bet ended up costing him $8,000 -- and according to his granddaughters, he never bothered to collect his winnings.