From Manhattan, Michael follows his Appleton's Guide east, travelling on the Long Island Railroad. He begins in Brooklyn, where he learns the incredible story behind the world's first steel suspension bridge.Divided by a common language, Michael struggles to order a pizza before continuing to Queens and the site of an ambitious engineering project that will transform New York City's rail network.

Moving east through Long Island, he visits one of the country's most decadent mansions, owned by an oil tycoon known as Mr Monopoly, where he gets into a flap dancing the Charleston, before ending his journey on Long Island's eastern most tip at New York's first lighthouse.

Michael Portillo continues his railroad journey through New York State following his Appleton's Guide. Beginning in the city of Poughkeepsie, he visits a famous all-female university, alma mater of Jane Fonda and Meryl Streep. He discovers the tumultuous history of the Poughkeepsie-Highland Railroad Bridge and follows the train line up to the Catskill Mountains, admiring its picturesque scenery from an altogether different type of line - a zip wire.

Back on safe ground, he discovers that the dramatic landscape inspired artists of the Hudson River School. Arriving in New York's state capital, Albany, he samples a drop of Albany Ale before rubbing shoulders with the State Senator.