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Michael Portillo embarks on a new railroad journey following his 1879 Appleton's guidebook from the city of brotherly love, Philadelphia, 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 its 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, Michael reflects on the 19th-century Pennsylvania system of incarceration at the Eastern State Penitentiary, before heading to the gambling resort of Atlantic City and its famous boardwalk.