1 INTRODUCTION: RETHINKING THE UNDERGROUND RAILROAD he nineteenth century’s most celebrated black American first Ttasted freedom on September 4, 1838, when he arrived in New York City as a nineteen-year-old fugitive slave. Frederick Bailey had long hoped to escape from bondage. As a youth in Maryland he gazed out at the ships on Chesapeake Bay, seeing them as “free- dom’s swift-winged angels.” He secretly taught himself to read and write, understanding, he later wrote, that knowledge was “the path- way from slavery to freedom.” In 1836, he and four friends devised a plan to abscond by canoe onto the bay and somehow make their way north. But the plan was discovered, and before their departure the five were arrested, jailed, and returned to their owners.1 Two years later, while working as a caulker in a Baltimore ship- yard, Bailey again plotted his escape, this time with the assistance of Anna Murray, a free black woman he planned to marry. She provided the money for a rail ticket, and Bailey borrowed papers from a retired black sailor identifying him as a free man. Dressed in nautical attire, he boarded a train, hoping to reach New York City. Maryland law required black passengers on the Philadelphia, Wilmington, and Baltimore line (which opened only a year before Bailey’s escape) to apply for tickets before eight o’clock in the morn- gateway to freedom pass5.indd 1 10/31/14 9:13 AM 2 gateway to freedom ing on the day of travel so that their free papers could be examined and, if necessary, investigated. But the measure remained largely unenforced. Bailey used a printed timetable to arrive at the station at the moment of the train’s departure and purchased his ticket on board to avoid scrutiny. Despite the short distance—less than 200 miles—the trip proved arduous and complicated. Thirty-five miles north of Baltimore the passengers had to disembark to cross the Susquehanna River by ferry. At Wilmington, they boarded a steamboat for Philadelphia. There, Bailey later recalled, “I enquired of a colored man how I could get on to New York.” The man directed him to a depot where Bailey took a ferry to Camden, New Jersey, then the Camden and Amboy Railroad to South Amboy, then another ferry across the Hudson River to a dock at the foot of Chambers Street. Less than twenty-four hours after leaving Baltimore, he disembarked on free soil. “A new world burst upon my agitated vision,” he would later write.2 In spite of his exhilaration, Bailey was frightened and alone, and he had no real plan about what to do next. He encountered Jake, a fugitive slave he had known in Maryland, who warned him that although they were in a free state, slave catchers roamed the city’s streets. Shortly thereafter, a “warm-hearted and generous” black sailor directed him to the home of David Ruggles at 36 Lispenard Street, not far from the docks. Ruggles was secretary and prime mover of the New York Committee of Vigilance, founded three years earlier to combat an epidemic of kidnapping. Many years before Solomon Northup drew attention to this problem in his widely read memoir, Twelve Years a Slave, free blacks, frequently young children, were abducted on New York’s streets for sale into southern slavery.3 The committee also provided fugitives from the South with shelter, transportation, and if they were apprehended, legal representation. By 1838, Ruggles was the leader of a network gateway to freedom pass5.indd 2 10/31/14 9:13 AM introduction: rethinking the underground railroad 3 with connections to antislavery activists in Baltimore, Philadel- phia, New England, and upstate New York. He regularly scoured the wharfs, on the lookout for fugitive slaves. Ruggles took Bailey into his home and advised him to change his name to help avoid recapture. Frederick Bailey now became Frederick Johnson. Rug- gles then gave him his first introduction to antislavery activities and mailed a letter to Anna Murray, urging her to come to New York at once. A few days later the couple married in Ruggles’s parlor. The Reverend James W. C. Pennington performed the ceremony.4 Like Bailey, Pennington (born James Pembroke) was a fugi- tive slave. He had escaped in 1827, at the age of twenty-one, from Washington County, Maryland, just south of the Mason-Dixon Line, leaving behind his parents and ten brothers and sisters. Pem- broke’s journey to freedom proved far more harrowing than Bai- ley’s. He started out on foot, but with “no knowledge of distance or direction,” he ended up heading southeast, toward Baltimore, not north. He received advice from a number of people, white and black, about how to avoid slave catchers, but at one point a group of men seized him, hoping to claim the $200 reward his owner had advertised for his return. Pembroke managed to escape from his captors and eventually made his way to southern Pennsylvania, where a Quaker couple, William and Phoebe Wright, sheltered him for six months, paid him for work as a farm laborer, and taught him to read and write. Pennington moved on to New York City in 1828. He found a job in Brooklyn, attended classes in the evening, and became a teacher in a black school on Long Island. By the time he officiated at the Baileys’ wedding, Pennington had become pastor of a local Congregational church.5 Unlike Pennington, Frederick Bailey did not remain in New York. He considered himself “comparatively safe,” but Ruggles appreciated the precarious situation of fugitives in the city. Soon after their wedding he gave the couple five dollars (more than a gateway to freedom pass5.indd 3 10/31/14 9:13 AM 4 gateway to freedom week’s wages for a manual laborer at the time) and told them to head to New Bedford, Massachusetts, where another black abo- litionist would receive them. A major port city, New Bedford was the world’s whaling capital. Its shipyards and oceangoing vessels provided employment to many free blacks and escaped slaves. Indeed, because of its strong abolitionist movement and thriving black community long accustomed to sheltering runaways, the city was known as the “fugitive’s Gibraltar” (or, as a Virginia newspaper put it, “a den of negro thieves and fugitive protectors”). In the fall of 1838, having discovered that in New Bedford, Johnson families were “so numerous as to cause some confusion in distinguishing one from another,” Frederick Bailey changed his name one last time. Henceforth, he would be known as Frederick Douglass.6 I It is impossible to say how many slaves escaped to freedom in the decades before the Civil War. Contemporary sources are often of little help. For very different reasons, both abolitionists and slave- owners had a vested interest in exaggerating the numbers—the former to emphasize the black desire for freedom and their own efforts “like noble heroes . for suffering and oppressed human- ity,” the latter as evidence of a northern conspiracy to undermine the peculiar institution. Estimates—guesses, really—suggest some- where between 1,000 and 5,000 per year between 1830 and 1860. This was hardly enough to affect the growth of the slave population (which approached four million in 1860), but sufficient to become a cause of alarm in the slave states and of contention between North and South, not to mention significant monetary loss for affected slaveholders.7 There were enough escapes that the southern physician Sam- uel A. Cartwright claimed to have identified a malady previously gateway to freedom pass5.indd 4 10/31/14 9:13 AM introduction: rethinking the underground railroad 5 unknown to medical science: “drapetomania,” a “disease caus- ing Negroes to run away.” (Frederick Law Olmsted, the New York journalist and landscape architect who wrote popular accounts of his visits to the South in the 1850s, noted that white servants had long been known to abscond. Perhaps, he suggested sarcastically, blacks had caught this disease from them.) Each escape had its own character and faced its own dangers, but those of Douglass and Pennington were in some ways typical. Most fugitives, like them, were young men who escaped alone. Those with immediate fami- lies often sought to retrieve their wives and children after reach- ing the North. Some, like Douglass, planned for months; others, like Pennington, decided to run away because of an immediate grievance—in his case, his owner’s threat to whip his mother for insubordination.8 All fugitive slaves faced daunting odds and demonstrated remarkable courage. Slave patrols and armed private groups ded- icated to apprehending fugitives could be found throughout the South. Their numbers were augmented following Nat Turner’s rebellion in Southampton County, Virginia, in 1831, which resulted in the death of over fifty whites. The authorities regularly searched ships, railroad cars, and highways for fugitives. In the slave states, to aid a runaway slave carried severe legal penalties. Most slaves had little knowledge of geography or how to locate sympathetic per- sons outside their immediate neighborhoods, although many seem to have been aware that there were people, black and white, will- ing to help them. They often envisaged dangers even greater than those that actually existed. In the first of his three autobiographies, published in 1845, Douglass recalled that he imagined watchmen everywhere—“at every ferry a guard, on every bridge a sentinel, and in every wood a patrol of slave hunters.” He memorably explained his anxiety by asking the reader to imagine himself in “a land given up to be a hunting-ground for slaveholders .