On the morning of April 16, 1848, three slaves belonging to Francis Dodge Jr. were missing. He wasn’t alone. Forty other local slave owners were missing a total of 77 slaves. That number included 15-year-old Mary Edmonson and her 13-year-old sister, Emily, two intelligent and attractive young women from Montgomery County who fled with four of their older brothers.

The plan had been in the works for some time. For several years, New York abolitionist William Chaplin had been working with black activists in Washington to free slaves. This was their most audacious plan so far. In March, Chaplin wrote to wealthy New York abolitionist Gerrit Smith — the likely financier of the venture. Chaplin told Smith that they were waiting for a ship and that “[t]he number of persons here, who are anxious to immigrate, is increasing on my hands daily — I believe there are not less than 75,” including two sisters “of great interest” as well as their brothers.

One month later, a 54-ton vessel named the Pearl tied up at a quiet spot near the Seventh Street wharf. By prearranged signal, the escapees quietly slipped through the streets, crossed the Mall, where construction was just beginning on the Washington Monument, and made their way onto the ship. Their destination — by way of the Potomac River south to Chesapeake Bay, then up the bay to the Chesapeake & Delaware Canal — was freedom in the North.

Inside the ship, Mary and Emily Edmonson settled on boxes placed between two portholes with their brothers surrounding them. A few small lanterns illuminated the faces of their fellow fugitives — adults and children — who bore the surnames Bell, Brent, Calvert, Dodson, Marshall, Pope, Queen and Smallwood — names well known here today. Some, including Mary and Emily, were related to free blacks who already owned homes. The slaves who crowded together in the Pearl’s hold on that April night in 1848, 13 years before the outbreak of the Civil War, were forebears of Washington’s black middle class.

Near midnight, the schooner pulled away from a drizzly city, where slave traders legally operated in and around the Center Market at Seventh Street and Pennsylvania Avenue NW, about a mile north of the wharf. But when Sunday dawned under a blanket of still fog, the ship’s two white captains, Daniel Drayton and Edward Sayres, had barely budged the ship past Alexandria. Inside the cramped quarters, the passengers anxiously prayed for wind. By afternoon, the sun broke through the clouds and a brisk breeze filled the sails of the little schooner. The Pearl was finally on its way down the Potomac.

The sisters began an incredible journey that spring, one that extended far beyond 1848. Ordinarily, scant information would be found concerning two enslaved teenage girls from Montgomery County. But there is, in fact, a wealth of information.

The Pearl soon ran into trouble. It had the misfortune to pass a steamer whose captain made note of the suspicious-looking schooner and reported its movements on reaching Washington. Then, when the Pearl reached the mouth of the Potomac, a fierce storm cut off any chance to sail up Chesapeake Bay.

The Pearl was towed back to Washington, where angry crowds began to gather. With all of the men’s hands bound, the fugitives were marched north from the steamboat wharf to the D.C. jail at Judiciary Square. Drayton reported that when the procession approached the hotel where slave trader Joseph Gannon plied his business — the current site of the National Archives — Gannon lunged at him with a knife. Authorities threw the two captains into a horse-pulled hack to haul them safely to jail.

Attention shifted quickly to the slaves. A voice from the crowd taunted Mary and Emily, asking them if they were ashamed for causing all this trouble. Emily replied that they would do the same again. When the girls’ brother-in-law John Brent saw the runaways paraded by — the brothers shackled and Mary and Emily walking with their arms around each other’s waist for support — he collapsed in the street.

Like many African American families in the Washington area, Mary and Emily’s was an amalgam of free and enslaved individuals intertwined through marriage and circumstance. According to the 1850 U.S. Census, the population of the District of Columbia was just over 43,000. About 10,000 were free African Americans. About 3,600 were enslaved.

Paul Edmonson, Mary and Emily’s father, was listed as a free man in a special 1832 Maryland census conducted for the purpose of encouraging free blacks to emigrate to Liberia. He chose to stay and three years later purchased 20 acres in the Norbeck area of Montgomery County, just east of what is now Georgia Avenue. Twelve years later, just months before six of his children boarded the Pearl, he purchased another 20 acres.

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In 1848, 77 enslaved African Americans, including the Edmonson sisters, attempted to escape their bondage in Washington, DC, by fleeing north to freedom via the ship the Pearl. Unfortunately, unfavorable winds slowed their escape, the ship was captured, and the escapees were brought back to Washington. This newspaper article details the attempted escape, capture, and a minor riot which broke out on the land that would become the National Mall as the Pearl’s passengers were transported to jail.

The Underground Railroad Virginia Midwest and South – Haki Kweli Shakur