On the night of April 15, 1848, at about 10 pm, the Pearl, a small rickety schooner departed from the Wharf in Southwest Washington with 77 enslaved persons. The escapees were assisted by Daniel Drayton, the captain in charge of the ship and Edmund Sayres, the captain in charge of the cargo. Paul Jennings, an enslaved person of Senator Daniel Webster approached Daniel Drayton earlier in March 1848 to plan the escape. The Pearl departed Washington from the Anacostia River and sailed down to the Potomac River in Alexandria where it spent the day.

The next day the Pearl set sail for the Chesapeake River, but the trip was interrupted due to a windstorm. Sayres ordered the ship to take refuge at Point Lookout, and Drayton agreed because he was convinced that they were safely out of the reach of slaveholders in Washington.

Slaveholders in Washington quickly recognized that many of their servants were nowhere to be found; and it was discovered that the chores regularly performed by them were left unattended.

Immediately upon recognizing an escape of enslaved persons had occurred, a steamship quickly sailed 140 miles down the Potomac River and captured the Pearl at Point Lookout with the captains and 77 escapees.

Emily and Mary Edmonson were among the fourteen children on the Pearl. All of the escapees, including the Edmonson sisters were transported back to Washington and incarcerated in the local jail. Emily and Mary were sold to slaveholders from New Orleans, a market known for fancy girls. They were returned to Alexandria, and a campaign was lead to free them. On November 4, 1848, Emily and Mary were freed, and they became instance celebrities. As celebrities, they united with Frederick Douglass in the abolitionist movement.