From Slavery to Freedom


“Give him a bad master and he aspires to a good master; give him a good master, and he wishes to become his own master”


After Douglass’ first failed attempt to escape he was sent to Baltimore to live with Hugh Auld, brother of Thomas Auld. His master never found prove that he intended to run away but he was not a welcome slave in St Michael. Baltimore had a large ship building industry and Douglass was hired as an apprentice to William Gardner. He learned how to caulk ships and worked side by side with white workers for a short period of time until the white workers found out that he was not a freedman and declined to work. He was severely beaten.

Hugh Auld found Douglass another apprentice job. He worked hard to learn and after a year he had become one of the most productive workers earning the highest wages. But at the end of the week he was obliged to give all his earning to Master Auld.

Most colored workers in the shipyard could read and write and attended the East Baltimore Mental Improvement Society. Douglass was dissatisfied even though he enjoyed more freedom than he had previously in the plantation. He started planning his escape, but this time he had to make sure he would be successful.

Plan to escape

It was 1838 and Douglass was 20 years old. He was determined to escape but he needed to save money so he hired his own time as a caulker. Planning his escape from Baltimore to the north was a difficult task. Trains were constantly watched for runaway slaves, free colored people needed free papers and could not ride at night and during the day they were fully inspected. Steamboats were under the same regulations.

The only way for him to escape was to obtain free papers. Free colored men owned free papers which included a description of the holder with the name, age, height, weight, visible scars, shape of face and body and any other marks that would help identify the holder of the document. A free man would lend his free papers to the fugitive and have it returned ones he/she had reached his destination. This was a very dangerous operation for both the lender and borrower and an act of total trust as the lender was in danger of losing his freedom. Because of Douglass’ physique it was difficult to find a free colored man that met Frederick’s physical description, though many were willing to sacrifice. Douglass had a friend who was a sailor who lent him his papers, a sailor’s protection which served much as free papers. The description did not totally match Frederick but he was willing to risk it.

On the Underground Railroad


Underground railroad map

The Underground Railroad was a network of secret routes and houses that led slaves to freedom in northern states or in Canada.

The day of his escape was Monday September 3rd, 1838. He dressed as a sailor and played its part, he had thorough knowledge of ships and could talk like a sailor. He boarded the train to Philadelphia aboard the colored people car when the inspector came to check for free papers.

“Seeing that I did not readily produce my free papers, as the other colored persons in the car had done, he said to me in a friendly contrast with that observed towards the others: “I suppose you have your free papers?” To which I answered: “No, sir; I never carry my free papers to sea with me.” “But you have something to show that you are a free man, have you not?” “Yes, sir,” I answered: “I have a paper with the American eagle on it, that will carry me round the world.”

He passed the inspection but not yet the danger. The train passed Maryland and then Delaware, another slave state in the border between slavery and freedom and therefore more risky for fugitive slaves. Once they reached the head of the Chesapeake Bay they had to cross the Susquehanna River by ferry. Once across the river they boarded the train again towards Philadelphia. In Philadelphia he waited until night to take the train to New York, he reached NY Tuesday morning. The journey from Baltimore to New York took him less than 24 hours.

Once in New York Douglass met a sailor named Stuart who took him to David Ruggles, the Secretary of the Vigilance Committee of the Underground Railroad. In NY he reunited with Ana Murray, who came from Baltimore as soon as she found out of Frederick’s save arrival, they were married by Reverent Pennington. Because Douglass’ occupation was that of a caulker they sent him to New Bedford, Massachusetts as it had a large ship building industry and would be easier to find a job in his trade. In New Bedford he started a new life as a free man.

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