On September 4, 1838, a twenty-year-old fugitive slave named Frederick Bailey arrived in New York City. He had long hoped to escape from bondage, gazing out at the ships on Maryland’s Chesapeake Bay as a child and seeing them as “freedom’s swift-winged angels.” He secretly taught himself to read and write, understanding, he later wrote, that knowledge was “the pathway from slavery to freedom.”
Bailey’s first attempt at flight came in 1836, when he and four friends devised a plan to abscond by canoe onto the bay and make their way north. But the plan was discovered, and the five…
