From Manhattan, Michael follows his Appleton's General Guide east to Long Island. Beginning in Brooklyn, he hears the moving story behind the construction of the world's first steel suspension bridge high above the East River. Below ground, he investigates the arrival of New York City's first subway and the dangers faced by the men who built it - the sandhogs.

At the Brooklyn Navy Yard, Michael discovers the dry dock where warships were built to defend American trade against the British and tastes the modern day moonshine now produced there. Michael follows in the footsteps of thousands of early 20th-century holidaymakers to what was once America's playground, Coney Island.

Continuing on the Long Island Railroad to Queens, Michael investigates the site of an ambitious engineering project that will transform New York City's rail network. A model town built by an Irish immigrant who became one of the richest men in America is Michael's next stop before he heads to the island's Gold Coast. There, Michael relives the fun of the roaring twenties at Oheka Castle, a vast private residence once home to a rail tycoon before becoming a weekend retreat for New York City's garbage men. In East Hampton, Michael discovers Home Sweet Home before ending his journey at the Montauk lighthouse on Long Island's easternmost tip.