Douglass's First Attempt to Escape Slavery
After working for Covey for a year, Frederick was sent to work for a farmer named William Freeland, who was a relatively kind master.
But by now, Frederick did not care about having a kind master. All Frederick wanted was his freedom. He started an illegal school for blacks in the area that secretly met at night and on Sundays, and with five other slaves he began to plan his escape to the North. A year had passed since Frederick began working for William Freeland and his plan of escape had been completed. His group planned to steal a boat, row to the northern tip of Chesapeake Bay, and then flee on foot to the free state of Pennsylvania. The escape was supposed to take place just before the Easter holiday in 1836, but one of Frederick's associates had exposed the plot and a group of armed white men captured the slaves and put them in jail.
Douglass first unsuccessfully tried to escape from Mr. Freeman, who had hired him out from his owner Colonel Lloyd. In 1836, he tried to escape from his new owner Covey, but failed again.