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 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.