The grand building sits at 21 Magazine Street

Constructed in 1802, the foreboding structure at 21 Magazine Street (pictured in 1933) served as a city poorhouse and hospital before being repurposed as Charleston’s Old City Jail. Operational through 1939, the jail housed some of the city’s most infamous inmates, ranging from 19th-century pirates to Lavinia Fisher, considered the first female serial killer in the United States. In 2016, Landmark Enterprises purchased the building and transformed it into the Twenty-One Magazine event venue during a seven-year, multimillion-dollar renovation. Its third floor now includes offices, while the ground level is available to explore during nightly excursions hosted by Bulldog Tours, where guides encourage keeping an eye out for ghostly visages of the formerly incarcerated.