Harriet Tubman and the Dover Eight

This is an excerpt from our book, "They Can't Pull Us Up: Harriet Tubman and Her Life", available on AMAZON.


Available now.

Harriet Tubman, not only escorted escapees to freedom, she also conducted escapes by sending messages and helping to coordinate support--without physically being there. 

Harriet Tubman

Henry Predeaux was enslaved in the Bucktown area in Dorchester County.  This is the same area of Maryland where Harriet and her family were enslaved.  Henry’s owner, one day, threatened to sell him south and in March of 1857 Henry decided to escape.  He was a large man, about 27 years old, and was determined to seek his freedom using the network of people who were willing to try to help escaped slaves.  He was also able to get instructions from Harriet Tubman…probably through her father, and he likely received help from Samuel Green.

Henry Predeaux set out on his journey with Thomas Elliot, Denard Hughes, Lavina Woolfley, James Woolfley, Bill Kiah, Emily Kiah, and at least one other person.   

These eight travelers made the long journey through the landscape of the Eastern Shore…navigating the wetlands, the wooded areas, and its marshes.  When they arrived in Dover, Delaware they were instructed to meet up with a man by the name of Thomas Otwell.  The eight men and women had been given instructions by Harriet Tubman, undoubtedly given to them through other people, and they followed the instructions every step of the way.  When they arrived in Delaware, they did not necessarily suspect that there would be any undue trouble.

Harriet Tubman's Childhood Home

Thomas Otwell was a black man who knew Harriet Tubman and apparently helped her on several of her journeys through Delaware.  Many times Harriet and others would pay people to perform certain tasks in support of the Underground Railroad--housing or picking up someone, escorting escapees to different places, etc.  These tasks were rewarded with a little bit of money to help ensure the assignment got completed and to provide the person with some type of reward for the risks they were undertaking.

Wetlands along the Eastern Shore of the Chesapeake Bay--near Harriet Tubman's most famous escapes.

Wetlands along the Eastern Shore of the Chesapeake Bay--near Harriet Tubman's most famous escapes.

By the time the eight men and women reached Dover, there was a $3,000 reward for their arrest.  Thomas Otwell was supposed to meet the Dover Eight and take them to the home of William Brinkly, an African-American man who sometimes helped escaped slaves get through that part of Delaware.  Otwell, instead of taking the eight people to Brinkly’s house, led them to the local jail.

He had notified the sheriff and others, ahead of time, that he would be bringing by the escapees.  It was night time, and it was a little difficult to see, as Otwell led them up the stairs...remarking that they were “cold, but would soon have a good warming.”  Once they got in, a light was lit and the eight men and women noticed the iron bars.  

A brutal fight broke out between the would-be captives and the sheriff and his men.  The group managed to make it down one flight of stairs and the brawl continued into the sheriff’s private apartment.

The sheriff’s wife and children were awakened and they began screaming and were scared for their lives.  Henry noticed a “shovel of fire” (used to help keep fire places going at that time) and spread its contents all over the floor.  This gave them a little bit of time.  The two women jumped through the window.  Henry then picked up an andiron (heavy iron supports used to hold wood inside a fireplace) and smashed out the rest of the window, through which the other men jumped.  The distance to the ground was about twelve feet and each of them made it out.  Upon hitting the ground they were faced with a wall surrounding the jail, but desperate times will bring out the best of physical efforts.  Seven of them made it over the wall…six of them managed to run off together but, for one of them, it was unclear where he went.

By the time Henry got on the other side of the wall, the sheriff was there facing him.  The sheriff stood there, “...in his stockings without his shoes” and pointed his pistol directly at Henry, but it did not go off.  

Henry was able to get away.


Letter from Thomas Garrett (Abolitionist

and Underground Railroad supporter)

Wilmington, 3d mo. 13th, 1857 (March 1857)

Dear Cousin, Samuel Rhoads:

I have a letter this day from an agent of the Underground Rail Road, near Dover,...saying I must be on the look out for six brothers and two sisters, they were decoyed and betrayed, he says by a colored man named Thomas Otwell, who pretended to be their friend, and sent a white (man) ahead to wait for them at Dover till they arrived; they were arrested...

....they broke jail; six of them are secreted in the neighborhood, and the writer has not known what became of the other two.  The six were to start last night for this place.  I hear that their owners have persons stationed at several places on the road watching.  I fear they will be taken....  I shall have two men sent this evening some four or five miles below to keep them away from this town,... 

Thee may show this to Still (William Still) and McKim, and oblige thy cousin,

Thomas Garrett.


The majority of the Dover Eight (including Henry) made it to William Still and the Vigilance Committee of the Underground Railroad in Philadelphia.  William Still documented their story and sent them on their way with help from the committee.

Area right around the corner from Harriet Tubman's childhood home.

Area right around the corner from Harriet Tubman's childhood home.

Several of the “Eight” were confirmed to have made it all the way to Canada, but nothing is known about what happened to Henry Predeaux after 1857.  This is just one example of the kinds of things people went through to gain their freedom.

You can read more about Harriet Tubman and some of the political actions that supported the existence of slavery in our new book.

Available HERE and on Amazon.

Copyright, Red and Black Ink, LLC 2016.


Maryland State Archives. Henry Predeaux (b. circa 1830 - d. ?).

Still, William.  The Underground Railroad:  A Record of Facts, Authentic Narratives, Letters, etc.  Philadelphia:  Porter & Coates, 1872).


Harriet Tubman, full-length portrait, standing with hands on back of a chair.  Lindsley, H. B., photographer, between ca. 1860 and 1875]

Red and Black Ink, LLC photos, Eastern Shore of Maryland.

Danita Smith