Horatio Nelson Jackson finds himself at the University Club in San Francisco, CA in May of 1903. He makes a $50 bet with a fellow patron that will change his life (and the world!) forever.

Swipes agrees to fund the trip, but only if Jackson can convince Sewall Crocker - the young man who recently gave a driving lesson to the couple - to accompany him. 

Driving through northern CA without proper roadmaps, Jackson & Crocker must rely on directions from strangers, including a mysterious red-haired woman on a white horse. 

The duo begins their difficult journey into the Cascade Mountains. Their path is often blocked by obstacles like trees, boulders, and streams. They must get creative when rocks pop their tires.

The duo embarks on a harrowing ride into SE Oregon and suffers multiple breakdowns while crossing 200 miles of desert. 

Continuing across Idaho, the trio accidentally goes 80 miles the wrong way. Jackson loses his jacket and wallet, and heavy rains wash out the roads. They camp by the car at Green River. 

Two automobile manufacturers, Oldsmobile and Packard Motor Company, begin cross-country attempts in their new 1903 models, creating a race across the nation in the press.

The Vermont suffers its worst breakdown yet in Rawlins, WY and continues to struggle as the crew makes its way toward Nebraska.

When the trio reaches Omaha, the Winton Company offers to take over the drive and sponsor the rest of The Vermont's journey. 

The crew zooms across the upper Midwest, driving through Iowa, Illinois, Indiana, and Ohio in about a week. They stop in Cleveland at the Winton Factory, where The Vermont was made. 

After the accident, The Vermont is bruised, but not broken. The trio gets an update on Packard and Oldsmobile. They approach NYC after passing Schenectady, Albany, and Poughkeepsie.

Jackson and his wife Bertha are reunited at the end of the race. Jackson assesses his physical and financial losses, despite winning his bet. The celebration continues in NYC. 

After making the bet, Jackson returns to his wife Bertha (also known as Swipes) and asks for permission -and funding- to complete his automobile adventure across America. 

Jackson and Crocker have packed up their motorcar (named The Vermont) and head north from San Francisco to try to avoid the sandy deserts of Nevada. 

Jackson & Crocker sit around a campfire and discuss the obstacles and aspirations of their drive, and learn more about each other's backgrounds and motivations.

Jackson & Crocker stop in Alturas, CA for supplies to be delivered, but leave after waiting 5 days. A front spring breaks and they crawl to the next town under 10 mph. Supplies arrive 3 days later.

Despite difficult days of driving through deserts and downpours, the duo decides to adopt a dog named Bud in Idaho.

Jackson and his wife Bertha (Swipes) exchange letters between WY and VT.. Swipes provides support and Jackson expresses confidence as The Vermont approaches Rawlins, WY. 

The trio wanders through the wilderness of Western Wyoming. They encounter a shepherd who feeds them and leads them to the nearest railroad to help get their route back on track. 

Massive storms in western Nebraska dampen the roads, but not the mood. The terrain gets easier as the Vermont zooms toward Omaha.

Alexander Winton sings about Jackson, Crocker & Bud making their historic drive across the nation, and the dawn of the automobile revolution.

The Vermont drives along the coast of Lake Erie to avoid the Allegheny Mountains. After days of downpours, they arrive in Buffalo, NY on July 23. East of Buffalo, The Vermont gets in an accident. 

The trio drives through the night, and arrives in NYC at 4:30am on July 26, 1903. They reflect on the impact of their accomplishment, and the next day is full of crowds and celebrations.

Jackson, Bertha, and Bud start driving back to Burlington in The Vermont on July 30. The journey home takes over a week. As Jackson finally pulls the car into his own shed, the drive chain snaps.