-The slave breaker- had Frederick beaten daily for the slightest violation of his strict rules. After spending approximately six months working for Edward Covey, he was then sent to work for a farmer named William Freeland, who was a relatively kind master. But, by this time Frederick had not cared about how nice his master was. The only thing Fredrick cared about, was gaining his freedom. He started an illegal school for blacks, in which he and five others would meet after hours to plan escape routes. .
A year had passed since Frederick began working for William Freeland and his plan of escape had been completed. They planned to steal a boat, row to the northern tip of Chesapeake Bay, and then flee on foot to the free state of Pennsylvania. Their plan was jeopardized when one of Frederick's associates exposed the plot, and they were captured and thrown into jail. During the week Frederick spent in jail, he feared that he would be sold to a plantation deep in the south, where slavery was said to be very harsh. To his surprise, Thomas Auld, (his previous master) came and released him from jail and he was sent back to his first master Hugh Auld. .
Frederick was now 18 years old, 6 feet tall and very strong from working in the fields. Hugh Auld decided that Frederick should work as a caulker (a man who forced sealing matter into the seams in a boat's hull to make it water tight) to earn his keep. During this time he learned to write by tracing the letters on the sides of these ships. In Frederick's spare time, he met with a group of educated blacks who had formed an association called the East Baltimore Mental Improvement Society. At one of the society meetings, Frederick met a free black slave from Baltimore, Anna Murray, who was a servant for a wealthy Baltimore family. They fell in love and became engaged in 1838. .
In September 1838, Frederick obtained papers supplied by a free black seaman and, dressed as a sailor just back from sea duty, took a train from Baltimore to New York.