The Charlton Street Gang was one of the earliest river pirates raiding small cargo ships in the North River of New York Harbor during post-Civil War period of the 1860s. With the well protected ocean liners and major shipping vessels reserved for the Manhattan Westside dockyards however, the gang began to raid merchant shipping upriver.
Under the leadership of Sadie the Goat, the gang stole a sloop in 1869 and soon began raiding merchant shipping and raiding homes along the Hudson River from the Harlem River as far as Poughkeepsie and Albany, New York. Flying the flag of the Jolly Roger, the gang was extremely successful soon becoming known for kidnapping wealthy men, women, and children for ransom. According to newspapers of the period Sadie the Goat allegedly had forced several male victims to walk the plank. However after several victims had been murdered by the gang local Hudson Valley residents formed a vigilante group and, after several members were killed in a series of violent battles, the gang decided to return to the New York waterfront where they returned to street crime eventually dissolving by the end of the decade.