African American History Is American Hstory
African American History Is American History
African American History Is American History 

Lesson Plan 4 - The Underground Railroad in the South


            One of the most amazing parts of the history of the Underground Railroad is the story of how 100,000 slaves managed to successfully flee from the South when law enforcement  in every southern  state was designed to prevent their “slave property” from escaping. Every freedom seeker was faced with a barrage of officials whose duty it was to monitor the movements of all of the slaves living in their region. First there were lawmen of every description from local sheriffs to federal marshal. In addition there were civilian patrollers and professional slave hunters who regularly searched the fields, forests and swamplands with their dreaded blood hounds wherever there was a report of a suspected runaway in the neighborhood. These searchers were frequently joined by  farmers, laborers and other simple folk who hoped that they might collect a little reward money.

            If they were caught, and so many fleeing slaves were caught, the punishments were severe. Whippings, brandings, and mutilation of a runaway were not uncommon.  Some recaptured slaves were beaten to death.  Yet in spite of the risk thousands of slaves made the choice to run away. How did so many of them succeed?

            While a few fugitives succeeded in reaching the North completely on their own and others relied only on family and friends many thousands more succeeded with the help of the South’s secret but well organized Underground Railroad. The Railroad’s hidden weapon was the existence of the thousands of African American watermen (most of them slaves) who played a vital role in the South’s coastal economy.

In the days before railroads crisscrossed the American landscape( most railroad lines even in the 1850 were just local routes)  the only way to move goods economically  from the plantation  to the city was through  the extensive river systems that covered the region. Rivers flowed from the foothills of the Appalachian Mountains down to the south’s sea port cities. A flotilla of vessels of every size and description carried the cotton, tobacco, rice, corn, pork and lumber to a seaside port where sailing ships carried them off to markets in the North and to Europe            The pilots and crew of these vessels were an incredibly skilled collection of men who were expert in navigating these dangerous waterways. They knew every twist and turn of the rivers along their journey.  They had to learn the whereabouts of every swift current, unexpected shallows, and dangerous shoals that were part of every trip they took back and forth down their waterway.  Very few white southerners ever piloted a vessel down one of these vital river highways.  Without these master pilots the South’s economy would collapse.

            Some of these slave pilots were also key figures in the Underground Railroad. Since most of the pilots traveled alone for days and sometimes weeks unsupervised by any white man, they were free to smuggle freedom- seeking men and women aboard their vessels. Piles of cotton, tobacco, and corn made wonderful hiding places.  When a fugitive reached a port city and had to be moved from the safety of the ship into the dangerous world of the city Underground Railroad workers was ready.

            Every wharf district in the South teemed with black workers. Slave stevedores carried cargo on and off vessels. Other workers repaired sea going ships as they lay at anchor. There were always a group of workers busy repairing some part of the dock’s structure.  Women were a key element of the wharf economy. Black laundry women brought newly washed clothes aboard the ships and wandered unnoticed in and out of the cabins. Cleaning ladies kept the ships spotless. Market women carrying food and other supplies sped up and down the gangplanks of every ship getting ready to sail. Among all this hustle and bustle Underground Railroad agents were able to slip hundreds of fugitives aboard north going sailing vessels. Robert Purvis, one of the most important black leaders of Pennsylvania’s Underground Railroad, reminded William Still in a letter written after the Civil War that  “The most efficient helpers or agents that we had were two market women, who lived in Baltimore, one of whom was white, the other “colored”.[1]                        

            Southerners acknowledged that these waterways and port cities had become a sieve through which their slaves escaped to freedom. The Wilmington Journal complained  that “ It is almost an every day occurrence for our negro slaves to take passage [aboard a ship] and go North” [2] While the Norfolk American Beacon insisted that slaves were escaping almost daily from their city. In 1854 the same newspaper estimated that Norfolk, Virginia had lost more than $30,000 worth of slaves that year alone. Yet what could slaveholders do to prevent this endless problem of runaway slaves? Their entire economy depended on the skills of these talented slave pilots since  cotton could only be transported by river boats. Port cities needed a well functioning wharf to attract sea going vessels and without slave labor the entire wharf economy would collapse.  




The story of Captain Daniel Drayton gives us a glimpse of just how the South’s Underground Railroad operated. Even though the rescue failed his story illustrates how the Railroad influenced the dynamics of the struggle to end slavery.  

Drayton’s story began one evening in the summer of 1847 in the nation’s capital.  as the captain sat smoking his pipe on the deck of his ship.  An elderly black man boarded the boat and began a seemingly casual conversation with Drayton.  Within this random chatter a few key questions had been asked. The black man confirmed that Drayton was from the North. He offhandedly mentioned the fact that he had been told that most northerners were abolitionists. The captain paused for a long moment then nodded in agreement. Daniel Drayton explains in his autobiography why this was such a turning point in his life.

Drayton’s life had been an ordinary one filled with the normal ambition to succeed that was the goal of most Americans. Then after almost dying from yellow fever Drayton went through a religious conversion. Drayton explains what happened next “I no longer considered myself living for myself alone. I regarded myself as bound to do unto others as I would that they should do unto me”.[3]  For years Drayton had sailed regularly into southern ports without being disturbed by the morality of slavery. Drayton was never fooled by slaveholders who insisted that their slaves are totally happy and content. It is only mischievous white people from the north who put the idea of running away into their heads.

In his autobiography Drayton states just the opposite  “But there is not a waterman who ever sailed in Chesapeake Bay who will not tell you that, so far from the slaves needed any prompting to run away when they ask you to assist them, to make them take no for an answer. I have known instances where men have lain in the woods for a year or two, waiting for an opportunity to escape on board some vessel. ”[4]  

For years Drayton had resisted these appeals but now he was a changed man. 

This time he nodded his head in agreement knowing that he was committing himself to a new cause. This elderly black man waited a moment before he continued the conversation. This was the dangerous moment  He had no way of knowing whether Drayton was a friend or he might be a spy working for southern officials who were constantly trying to identify slave rescuers. If Drayton was a spy this courageous black man would be facing a severe punishment which could be anything from a beating, jail time, sold on the auction block, or even death.  The man took a deep breath and said to Drayton that he knew of a black woman and her five children who desperately needed to escape. Will you talk to her? The captain’s answer was a solemn yes.  

The mother and her children were smuggled aboard the ship and ten days later the family landed on free soil. It was soon after this successful rescue mission that Captain Drayton received a letter from William Chaplin.

               Chaplin was a member of Boston’s elite and a committed abolitionist who in 1846 had just arrived in Washington D.C. He was a reporter for a number of antislavery newspapers. Chaplin also had another mission which was to rebuild the city’s Underground Railroad. In the 1840’s the nation’s capital had had a thriving Underground Railroad which was led by two men Charles Torrey and Thomas Smallwood. Authorities in both Washington and Maryland were determined to destroy this threat to their “peculiar institution” In 1846 they issued warrants for the arrest of the two men. Thomas Smallwood managed to escape before he was arrested but Charles Torrey was not so lucky. He was tried and convicted of the crime of slave stealing and was sentenced to serve six years in a Maryland jail.

            As soon as Chaplin heard about Drayton’s successful rescue he decided to bring Drayton into his network of rescuers. He wrote the captain a letter telling him that he knew of a number of slaves who were longing to escape. Was Drayton willing to help them? Yes the captain replied but he told Chaplin that there were several steps to be taken before such a rescue could begin. First Drayton would have to rent a ship large enough to hide a number of fugitives and Chaplin would have to raise the money for the rental.  Drayton told Chaplin that he needed to be paid for his time and trouble because, while he was a deeply committed rescuer, he needed to support  his wife and children . It took a while but Drayton finally found a ship owner , Edward  Sayres, who was willing to rent his ship, Pearl, for the rescue. Sayres even volunteered to join Drayton as part of the rescue team. 

            On April 13, 1848 the same day that Daniel Drayton slipped the Pearl into its moorings on the Potomac River, Washington D.C. was celebrating what people were calling  the new French Revolution because  the French people had just overthrown king Louis-Philippe and established the Second Republic.  As Drayton looked out over the city he could see huge bonfires and a grand torch light parade.  Senator Foote from the slaveholding state of Mississippi in one of the speeches during the celebration extolled the fact that this revolution held out the promise of the universal establishment of civil and religious liberty. Drayton thought it ironic that one of the loudest defenders  of slavery would announce such enthusiastic  support for liberty. 

Drayton had promised Chaplin that he was willing to transport as many fugitives as the ship would hold. When Drayton boarded the Pearl on Saturday night ready to set sail he was astonished to find seventy- eight fugitives hiding below deck eager to begin their journey north.

Drayton’s plan was to sail down the Potomac and reach the open sea before daybreak but the weather was against him. There was no wind so the ship could only move very slowly down the Potomac. The Pearl was never able to reach the Chesapeake Bay. On Sunday the weather was even worse. This time the wind blew with such a gale force that Dayton decided it was too dangerous sail his small sloop into the bay itself. The captain was forced to keep his vessel moored on the river for a second day. This delay was fatal for the success of the mass escape.

Meanwhile on Sunday morning many slaveholders  woke up to find  no breakfast on the table and  their servants missing  As the bewildered southerners began talking to one another they were shocked to realize that there had been a mass escape of slaves out of Washington. They rushed to consult with the local authorities about what to do next.  These slaveholders were in luck because of the treachery of one black drayman who told the authorities that he had seen groups of blacks slipping aboard the Pearl.   Washington D.C. magistrate W. C. Williams piled thirty armed volunteers on to the steamer, Salem and set out in hot pursuit of the Pearl. Two o’clock Monday morning Williams and his posse found the Pearl still anchored in the river. The fugitives, caught by surprise, had no chance to resist. They were chained and forced below deck. Drayton, Sayres, and English were arrested and taken aboard the Salem.

At seven- thirty Tuesday morning the city awoke to see 80 prisoners in chains being marched along Pennsylvania Avenue towards the jail. Among the fugitives were thirty eight men, twenty six women, and thirteen children, some of them infants in their mother’s arms. The prisoners had to face an angry mob that lined the street shouting curses and threats. The mob’s fury rose to a fever pitch when they saw rescuers Drayton and  Sayres. They began screaming lynch them! Lynch them! One man even leaped out of the crown and tried to stab Drayton.

President James Polk hoped that now because the fugitives had all been recaptured the capital would settle down. Washington D.C. however was a southern city surrounded by the slave states of Maryland and Virginia and angry southerners had just begun to wreak their revenge on those people who had organized the largest mass escape in American history.

The crowds singled out a few new targets to attack. The first was Chaplin  the suspected leader of the Underground Railroad but he, had been warned and he went into hiding. The second target of southern anger was Gamaliel Bailey the publisher of  one of the most prominent abolitionist newspapers, The National Era.  Tuesday night several hundred people gathered in front of the building that housed the newspaper and began smashing windows and doors. Only the intervention of the police prevented the crowd from destroying the structure. The next night an even larger crowd assembled in front of the building and demanded that the entire edifice be torn down. Only when Walter Lenox, a member of Washington D.C. Board of Aldermen along with other leaders of the community promised the mob that they would get Gamaliel Bailey, publisher of the National Era, to immediately stop publishing his newspaper did the crowd disperse.

A committee walked to Bailey’s home. They begged the publisher to take his press and leave the city before more violence broke out. Bailey told the delegation “that he would rather die than surrender his rights as a ‘representative of the free press”[5]  

While the committee was impressed by the publisher’s principles Bailey’s friends were even more worried about the safety of his family. When the waiting crowd was told of Bailey’s answer their response was to try once more to burn the structure down. Only the intervention of the police and a resolute group of prominent citizens managed to save the National Era building.

While the riotous crowd continued to challenge the police in front of the National Era Building a group of Bailey’s friends raced to his house, lifted up his six sleeping children and carried them off to a safe house. These friends were right to be concerned. As soon as the police forced the demonstrators to leave the National Era Building the frustrated mob hurried over to Bailey’s house with every intension of taring and feathering the publisher. Somehow Bailey managed to convince the throng that he had nothing   to do with the Pearl rescue and they left without harming him.

  For three days mobs seemed to be taking over the city. President Polk, in a desperate effort to bring peace back to the capital appealed to government clerks to help the police restore order. This expanded law and order battalion finally brought order back to the capital.  

President Polk was very worried by the violence that had broken out in the city. This spring, the president believed, American should be celebrating. The war with Mexico was over. The peace treaty had just been signed on February 2, 1848. Manifest Destiny, the belief that United States must possess all of North America, had been one of the main planks of Polk’s Democratic Party platform. Now that America stretched from the Atlantic to the Pacific Ocean the whole country should be rejoicing. But instead of the celebrations Polk was expecting something ominous was happening in the nation.

It began in December 1846 during a debate in the House of Representatives on an appropriations bill to fund the Mexican War. Surprisingly when Democratic Representative David Wilmont stood up to speak in support of the appropriations bill he offered an amendment  which changed the entire debate on the Mexican war forever. “that, as an express and fundamental condition to  the acquisition of any territory from the Republic of Mexico….neither slavery nor involuntary servitude shall ever exist in any part of said territory”[6] Shocked as he was by this abrupt reversal by one of his own party members President Polk expected most northern Democrats would support his demand to defeat the Wilmont Proviso and then go on to pass the appropriation bill. The president was stunned when  northern Democrats defied party discipline and voted with northern Whigs  to support the Wilmont Proviso. Polk never got his appropriation bill passed because in every session for the next fifteen years the Wilmont Proviso was passed by the House and defeated in the Senate. Something new had entered  America’s political life. No longer was the nation divided into the two political parties, Democrats and Whigs now the main split in the country had just developed between the North and South.

This division needed to be healed as soon as possible because Congress had to deal with the issue of slavery in the conquered territories. Polk worried that press coverage of the arrest of Captain Drayton and the Pearl fugitives would fan the flames of this sectional controversy.           

But with the capital engulfed in a three day riot there was no way that northern press would ignore such a story. Reporters continued to write stories about the fate of the fugitives. They wrote poignant articles about what they saw at the railroad station after the notorious slave trader, Hope Slatter ,purchased 50 of the Pearl fugitives. Reporters described how disturbing it was to see men and women chained like animals dragged to the depot and loaded onto the train like cattle. Other stories described how they saw hundreds of African Americans filling the streets in front of the station watching tearfully as the train pulled out carrying their loved ones away forever. One reporter described how “ A sobbing mother aboard the train told her teen aged son. “Be a good boy, and take care of your little sister,-We shall meet soon in heaven”. [7]         Southerners were still trying to convince Americans that it was the evil

Captain Drayton who had talked their 78 slaves into running away. They found it impossible to admit that southern slaves had the same desire to be free as Americans who had just that weekend celebrated the French revolution.   At the same time lawmen tried to convince Drayton to incriminate not only William Chaplin but  antislavery congressmen, Joshua Giddings and  Senator John P. Hale as the chief organizers of the escape. If he agreed to publically denounce  these three men lawmen promised Drayton they would drop charges against him. Drayton refused.     

The story of the Pearl fugitives remained a continuing issue because of the actions of William Chaplin.  Chaplin, as soon as he reached the safety of the North, began a campaign to rescue some of the prisoners who had still not been sold. While fifty captives had been sold to Hope Slatter and were beyond rescue there were others still waiting in jail.

Chaplin mounted a national campaign to raise enough money to purchase the freedom of at least a few of these captives. A group of prominent antislavery advocates quickly began their own  fundraising campaign and also reached out to other leaders in the antislavery community to join them in their crusade. Appeals were launched from the pulpit and the lecture circuit all over the North.  

Stories about the special plight that some of the captives faced shocked Americans when they learned that slave trading companies were placing a high price on some of these young girls. Reporters revealed that as one example the slave trading company of Bruin and Hill were demanding $2,250 for two sisters Mary and Emily Edmonson. (that would be over 45,000 today) When reporters questioned the reason why these young ladies were worth such a high price they were given this chilling answer. It was of course that in the South there was a great demand for attractive women. It was obvious to readers just why beautiful girls commanded such an extraordinary price. This was not just slavery it was prostitution a sin denounced in every church in America no matter whether you hated slavery or supported it.  Advocates all over the North redoubled their effort to free at least some of these young girls. They were somewhat successful. In spite of the prohibitive cost the money was raised to free the  Edmonson sisters. Some of the other captives were freed as well.

The publicity surrounding the rescue of the Pearl freedom seekers had an important effect on the struggle against slavery. Slaveholders had developed a public relations campaign that flooded the North with rosy pictures of plantation life. They promoted stories about a lovely peaceful world where a benevolent master became a surrogate father to his slaves. These slaves were always pictured(no matter what their age) as childlike creatures grateful for this tender loving care and repaying this devoted protection with a simple innocent adoration for  their masters. Now northerners were hearing a different story. Newspaper articles and lecturers were describing the real reason that seventy- eight slaves chose to take the risk of running away. Parents learning that they were about to be sold away from their children, the beatings and other harsh realities of slave life and then the final shattering of the caring master when  pictures of lovely young girls were held up during a lecture or published in the local newspaper with the plea that you can save this innocent young girl from being forced into a life of sin by just by donating whatever sum you can to rescue her.     

   Congress was also in an uproar over the Pearl rescue. The day after Drayton and Sayres were arrested Congressman Giddings  stood up in Congress and demanded to know just what crime the two men had committed. How he asked how in one day these two men had managed to steal 76 slaves from the homes of so many slaveholders. Was it really stealing when the so called “property” fled to you? A few days later Giddings delivered his most inflammatory speech stating that the Pearl Negros had “the same right to liberty as any Congressman”. [8]     

Southern Congressmen responded with anger. Senator John C. Calhoun of South Carolina declared that the Pearl rescue was a northern attack on a southern port  and stated that “slave escapes to be “the gravest and most vital of all questions to us and the whole Union”.[9] The debate over the Pearl raged unchecked for several days and was reported in newspapers throughout the nation. Giddings believed that the issue raised by the Pearl rescue had advanced the cause of antislavery more than any other event in recent years. He might have been right.  

That summer a new antislavery party was born, the Free Soil Party. The party’s  slogan was Free Soil, Free Speech, Free Labor and Free Men. In the election that fall the Free Soil Party elected 2 senators and 14 representatives. Because the Democratic and Whig Parties were almost equally divided in the 1849 House of Representatives  the Free Soil Party members played a pivotal role in deciding what legislation would be passed simply by voting with either the Democratic or Whig party.

The growing importance of this new antislavery party can be seen in the fate of the Pearl rescuers Daniel Drayton and Edward Sayers. The two men had been sentenced to 20  years for slave- stealing but in August 1852 Charles Sumner, the Free Soil senator from Massachusetts, approached President Millard Fillmore with a proposal to grant both men a presidential pardon, his request was quickly granted and both men were freed.      






Millstein Evelyn The Underground Railroad: A Movement That Changed America. St. Clair Press, 2015  Chapter 3  pg. 48-74

This chapter describes how the Underground Railroad operated in the South


Cecelski, David S. The Waterman’s Song: Slavery and Freedom in Maritime North Carolina.  Chapel Hill: The University of North Carolina Press, 2001

             This book is a remarkable study of the important role that black pilots played in the economy of the pre Civil War South and the part they played in the Underground Railroad. The last two chapters of the book tell how these seamen helped the Union win the war.


William Still The Underground Railroad. Chicago: Johnson Publishing Company Inc. 1970.

            This book originally published in 1872 is written by the head of the Underground Railroad in Philadelphia. The book describes the passengers who arrived in his office after escaping from the South.  Still kept a journal of the workings of the Railroad and it is the best source we have for learning how the Railroad operated in the South.





Potter, David.  The Impending Crisis 1848-1861. New York: Harper& Row 1976

(pg. 1-89)

            This book gives a very detailed description of the general political situation in the United States between 1846 and 1848 including the Wilmont Proviso and the founding of the Free Soil Party.




Buckmaster, Henrietta. Let My People Go: The story of the Underground Railroad and the Growth of the Abolitionist Movement. South Carolina: University of South Carolina Press,1941. (pg.152-156)

This book gives a good description of the Pearl rescue attempt.


Drayton, Daniel Personal Memoir of Daniel Drayton for Four Years ad Four Months A Prisoner (for Charity’s Sake) In Washington Jail. New York: Negro Universities Press reprinted 1969.


Harrold, Stanley. Subversives: Antislavery Community in Washington D.C. Baton Rouge: Louisiana State University Press, 2003 (pg. 116-145)

This book has the most complete description of Captain Drayton and the Pearl rescue attempt as well as an excellent account of the antislavery movement in the nation’s capital.


Harrold, Stanley. Gamaliel Bailey and Antislavery Union. Kent: The Kent s State University Press, 1986 (124-137)

This book is a good biography of an important player in the antislavery movement.


Stewart, James. Joshua R. Giddings and the Tactics of Radical Politics.  Cleveland: The Press of Case Western Reserve University, 1970 (pg. 103-160)

This book is an excellent biography of one of the leading antislavery members of the House of Representatives




Blue, Frederick. The Free Soilers: Third Party Politics 1848-54. Urbana: University of Illinois Press, 1973.

This book is an excellent study of this important movement


Sewell, Richard. Ballots for Freedom: Antislavery Politics in the United States 1837-1860. New York: W.W. Norton & Company, 1976.

This book is another outstanding study of antislavery politics during this era.


[1] Smedley, R.C. History of the Underground Railroad. New York: Arno Press and the New York Times, 1969 (pg. 355)

[2] Cecelski, David. The Shores of Freedom: The Maritime Underground Railroad in North Carolina 1800-1861. The North Carolina Historical Review April 1994 (pg. 177)

[3] Ibid (pg. 15)

[4] Drayton, Daniel. Personal Memoir of Daniel Drayton. Originally published in 1855 by Bela Marsh reprinted  New York: Negro University Press, 1969 (pg.22)

[5] Harrold, Stanley. Subversives: Antislavery Community in Washington D.C. Baton Rouge: Louisiana, Louisiana State University Press, 2003. (pg. 122)

[6] Potter, David M. The Impending Crisis.  New York: Harper & Row, 1976 (pg. 21)

[7] Harrold, Stanley. Subversives: Antislavery Community in Washington D.C. 1828-1865. Baton Rouge: Louisiana State University Press, 2003 (132)

[8] Stewart, James Brewer. Joshua R. Giddings and the Tactics of Radical Politics. Cleveland: The Press of Western Case University, 1970. (pg. 153)   

[9]  Harrold, Stanley. Subversives: Antislavery Community in Washington D.C. (pg. 142)

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