In the spring of 1848, a small schooner quietly left the Washington, D.C. harbor with 77 enslaved people on board, marking the largest recorded nonviolent escape attempt from slavery in United States history?
The plan was ambitious. The vessel was The Pearl, a modest two-masted sailing ship. Its goal was deceptively simple: sail from Washington, D.C., down the Potomac River, up the Chesapeake Bay, and ultimately reach freedom in the North. But behind that journey lay months of careful planning, brave conspirators, and an entire system designed to keep human beings in chains.
The escape was coordinated by a biracial network of abolitionists. Among them were William L. Chaplin and Gerrit Smith, white allies from New York, and free Black residents of Washington like Paul Jennings and Daniel Bell. Bell was a formerly enslaved blacksmith whose wife and children were still enslaved. For him, this wasn’t a cause—it was personal.
The captains hired to sail The Pearl were Daniel Drayton and Edward Sayres. Both white men, they had sympathies with the abolitionist cause. On the evening of April 15, 1848, they took aboard the 77 escapees, many of whom were women and children. They departed under the cover of night, hoping to reach the free state of New Jersey by way of the Atlantic coast.
However, fate intervened. The wind shifted southward shortly after departure, forcing the schooner to anchor near Point Lookout, Maryland. There they waited helplessly while slave owners in Washington began to realize what had happened. A furious manhunt ensued. A steamboat, The Salem, was quickly dispatched by enraged slaveholders, and within two days, The Pearl was captured and all escapees were returned to Washington.
The reaction was immediate and explosive. Washington’s pro-slavery faction erupted into riots. White mobs stormed through Black neighborhoods, destroying abolitionist property and threatening lives. One of the targets was the offices of the anti-slavery newspaper The National Era. Though few were killed, the violence demonstrated the fear and fury that slavery's defenders felt in the face of such bold resistance.
Most of the 77 individuals were quickly sold to traders and shipped to the Deep South, ensuring they’d never again be near family or allies. Yet, amid the tragedy, a few stories emerged with remarkable endings. Among the escapees were Mary and Emily Edmonson, teenagers from a devout Baptist family. Their father, Paul Edmonson, worked tirelessly to buy their freedom. With the help of Henry Ward Beecher—brother of Uncle Tom’s Cabin author Harriet Beecher Stowe—Paul eventually raised the funds. The sisters were freed and went on to become prominent figures in the anti-slavery movement. They even attended college, rare for African American women of their time.
Another lesser-known fact is that this failed escape directly impacted American politics. The incident caught national attention and became a focal point in the abolitionist press. It pressured Congress to address the intensifying conflict over slavery in the capital. Just two years later, as part of the Compromise of 1850, the slave trade was officially abolished in Washington, D.C. While slavery itself continued in the city until 1862, this legislative change was seen as a significant symbolic victory.
Captain Drayton, though tried and convicted, used his imprisonment as a platform. He published a memoir from his jail cell, outlining the operation and exposing the inhumanity of slavery. His words added fuel to the abolitionist fire and shifted public opinion in the North.
Though The Pearl never reached freedom, the story of its voyage resonated deeply across the nation. It revealed the extremes to which enslaved people would go for liberty—not just running individually through woods or by night, but coordinating a mass escape by sea. It also showed the extent to which abolitionists, Black and white alike, were willing to risk thei