Take this immersive journey into the gritty underworld of 19th-century Manhattan. This tour delves into the notorious Five Points neighborhood, and the 1st through 6th Wards, a melting pot of immigrants and the birthplace of America’s most infamous gangs. We will recount tales of gang leaders like Bill the Butcher and Boss Tweed, the corrupt politician. You’ll explore historic landmarks such as the site of the Old Brewery,  and the remnants of the Tombs prison. You’ll also see where the Ancient Order of Hibernians were founded. We will not only unveil the dark history of gang violence and political corruption but also provide a captivating glimpse into the social struggles and resilience of New York’s early inhabitants. A compelling way to experience the city’s turbulent past.

The River Pirates wreaked havoc along the Hudson and East Rivers. Figures like Sadie the Goat, who led the Charlton Street Gang raided ships, looted cargo, and smuggled goods, exploiting the chaotic, poorly policed waterfront. Their reign of terror, marked by theft and violence, sacking townships and kidnapping victims for ransom highlighted the era’s lawlessness. The formation of a specialized police unit, the Steamboat Squad by George Gastlin,  eventually curbed their activities by the 1880’s. This squad, patrolling the rivers and targeting the pirates’ hideouts, played a crucial role in dismantling the river gangs, restoring some semblance of order to the city’s bustling docks. We will highlight These stories and more when we visit the South Street Seaport during the tour.