.Anon thoughts of escape attempts entered his mind. Frederick was sure not to exclude his family and friend, and also his pupils. These included Henry and John Harris, Sandy Jenkins, Charles Robertson and Henry Bailey. Although Douglass was the youngest, he had some knowledge of the geography of the surrounding area and was very persuasive, so he became the leader of the pack. They were to escape in a stolen canoe and paddle to the head of Chesapeake Bay, then follow the North Star to freedom. Sandy withdrew from the plan following a nightmare about Frederick in the claws of a giant bird. On the day of the planned escape, as it happened, they were betrayed and jailed. Thomas Auld sent him to work with his brother Hugh and learn about trade and the caulking business. He made a promise at to Frederick at this time, if he behaved, he would be free by 25. Shortly, Douglass was transformed into a skillful caulker. He began to make friends at secret meetings he attended for free blacks, like the East Baltimore Mental Improvement Society. Here he met the love of his life, Anna Murray. They planned to marry as soon ad Frederick could escape. The time for his freedom was now. September 3rd, 1838, dressed as a sailor and carrying the papers of a retired black merchant sailor, he took a train from Baltimore to the Susquehanna River, crossed the ferry to Wilmington, Delaware, and never looked back. From there he traveled to Philadelphia by steamboat and caught another train to New York City. Eleven days later he and Anna were married by J.W.C. Peterson. They decided to settle in New Bedford, Massachusetts, to avoid the slave catchers who ran so rampant in New York. He would have been most happy as a ship caulker, but due to opposition by whites was forced to become a common laborer. The quality of life here was a big improvement from the South but racial prejudice was still far and wide.Frederick Bailey wanted to assume a name tha...
