Michael Portillo embarks on a new railroad journey, informed by his 1879 Appleton's guidebook, from the City of Brotherly Love south to the first permanent English colonial settlement in North America, Jamestown. He feasts on a gargantuan Philly cheesesteak, then looks to work off the calories with a run past the city's famous landmarks, in homage to one of Philadelphia's most famous sons, Rocky Balboa. All pumped up, he heads to Pennsylvania University to tackle the football team under the instruction of a fearsome coach. In the cradle of American independence, Michael discovers how, in 1776, liberty was proclaimed throughout the land yet millions remained enslaved. Alone in a cell at the Eastern State Penitentiary, Michael reflects on the 19th-century Pennsylvania system of incarceration, before heading to the gambling resort of Atlantic City. Michael hitches a ride with the Amish in a horse-drawn buggy, through rich Pennsylvania countryside. In Traintown USA, he joins the crew of the Strasburg Railroad. After oiling the magnificent engine, he rides on the footplate of the vintage steam locomotive. Next stop is the 'sweetest place on earth', where Michael learns about the world's largest chocolate factory and the town that bears its name. His last stop on this leg is Gettysburg, the most famous battlefield of the American Civil War, where, in 1863, President Abraham Lincoln made a momentous speech.