Billy begins his journey in Chicago, where he heads to the top of America's tallest building, discovers one of Al Capone's most notorious speakeasies and attends a gospel service in the suburb where rock and roll was born. Leaving the city behind, Billy visits the home of Abraham Lincoln, meets Illinois's champion pie-maker and encounters a 20-foot tall roadside giant. Finally, he heads into Amish country, where he takes the reins for a horse-drawn buggy ride.

Billy continues his journey in St Louis, Missouri, where he climbs the Gateway Arch and lunches at a restaurant where the chef is a soul music legend.

The comedian joins ranch hands on a cattle drive to Oklahoma City before heading into Texas, where he visits the ghost town of Glenrio and Devil's Rope Museum. In Los Alamos, New Mexico, he meets two men who helped create the atomic bomb and attends a rodeo in Arizona. Driving off-route, Billy ends the episode in Monument Valley, where he talks to a Navajo medicine man.

The comedian completes the last leg of his motor-trike journey along the world-famous Route 66. Billy visits a massive meteorite crater in Arizona, before heading to the Grand Canyon. He meets a campaigner trying to keep the historic route alive, and bottle-feeds a lion cub in a sanctuary for unwanted exotic pets. Finally he reflects on his 3,000-mile ride when he ends his travels in Santa Monica, California.