AUTHOR NOTE:
Every month here I feature a free book excerpt to give folks a taste of the style and content of the books I’ve written about the Delmarva Peninsula. September is the month when the great Frederick Douglass escaped slavery, so I thought I would include that chapter on that turn of events from my book, Tubman Travels: 32 Underground Railroad Journeys on Delmarva.
Each of the book’s 32 chapters tells a Delmarva-based Underground Railroad story from the life of an American hero (might be Tubman, might be Douglass, might be someone else), and each story is attached to a place you can go visit today to commune with these American heroes.
Here is where you can find info about Tubman Travels, including where to find it in stores, buy it from the author, or get it online. OK, on with this month’s excerpt!
CHAPTER 28
Fred Bailey Finally Finds His Way to Freedom
BIG PICTURE INTRO
In slavery, Frederick Douglass was known as Fred Bailey. The story of young Fred’s second run for freedom starts back in Talbot County, on the Eastern Shore of Maryland. That’s where Fred had plotted his first escape attempt with a group of friends, only to get betrayed and land instead in the Easton jail.
In the wake of that failure, Fred’s owner, Thomas Auld, sent Fred to Baltimore to live with and work for Auld’s brother, Hugh, and Hugh’s wife, Sophia. Fred had lived with this couple in Fells Point in his younger years, but the Baltimore he returned to at the age of 18 was a very different place from the one he knew back then.
During the five short years Fred had been away from Baltimore, the city had changed enormously. A gigantic wave of Irish immigration had led to a bitter, often violent rivalry over job opportunities, pitting these new white arrivals against the population of free and enslaved black locals. The tensions ran especially high in the shipyards of Fells Point, where trouble would find its way to Fred soon enough.
The Taste of Freedom
One day while Fred was on the job in a shipyard, a man named Edward North took a swing at him. North was the leader of a gaggle of white men who were always talking about how the “n******” were trying “to take the country” and “ought to be killed.”
Though still in his teens, Fred Bailey had reached a place in life where he wasn’t afraid to defend himself, despite his lowly legal status as a slave. He promptly picked North up and threw him into the Patapsco River.
On another occasion Fred got into a dispute with a white coworker over who did what wrong that caused a bolt to bend out of shape. One thing led to another, and soon, Fred was brawling with four white apprentices at the same time. A crowd of some 50 whites gathered around, many of them outraged by the sight of a black man swinging fists at white men.
Kill him!—kill him!
Kill the damned n*****!
He struck a white person!
Knock his brains out!
They pretty much did knock his brains out. When Fred got home, Sophia Auld took one look at his bloody face and burst into tears. Hugh Auld flew into a rage over the incident. He marched Fred down to the local Justice of the Peace on Bond Street, demanding the arrest of the men who had beaten up Fred. The Justice of the Peace did nothing.
After his failure in Easton, Fred had vowed that he would be better prepared to make a run at freedom the next time an opportunity presented itself. Whatever pennies he could set aside from his labors in the shipyards, he stashed away in a “Freedom Fund.” He searched high and low for a set of forged or borrowed papers that might help him pass as a free man on ships and trains.
In the spring of 1838, Fred cut a deal with Hugh Auld in which he won a measure of freedom to be in charge of his own life. He would be able to hire himself out to shipyards on the condition that he pay Auld $3 at the end of every week. He would also be able to move out of Auld’s house and into a place of his own, as long as he paid for everything out of his own pocket.
It was during this time that Fred helped form a club called the East Baltimore Mental Improvement Society. Members engaged in debate contests and learned classical theology and philosophy. Fred was already showing signs of a gift for public speaking. He used to bring down the house at society meetings with his parodies of white preachers. He also took up playing the violin, a hobby that he would stick with for a lifetime.
It was at a Mental Improvement Society social event that Fred met a young woman named Anna Murray. Like Fred, she hailed from the banks of Tuckahoe Creek on the Eastern Shore. Unlike Fred, she was legally free, being born one month after her mother received her manumission papers.
In time, Fred proposed to her. Anna said yes.
Getting Ready to Run
That August, Fred left Baltimore to spend a few days in the countryside at a religious camp meeting. He stayed longer than planned, then showed up one day late at Hugh Auld’s house to fork over that weekly $3 fee. Fred didn’t think this would be a big deal, but Hugh exploded in anger over his lapse. He ordered Fred to move back into his house. He also made a vaguely threatening comment about how Fred soon wouldn’t have to “trouble himself about finding work.”
Anna Murray Douglass
Fred wasn’t ready to run quite yet. He gave himself a deadline of three weeks. His fiancée, Anna, responded to this turn of events by selling a bed she owned and then giving the proceeds to Fred. She also contributed to his Freedom Fund out of her own savings.
By Monday, September 3, 1838, he was ready. He hadn’t found the perfect “freeman’s papers,” but he had gotten his hands on some sailor’s “protection papers” that might be good enough to get him on board a train in the guise of a merchant seaman.
When Fred showed up at the train station in Baltimore, he had his every step carefully mapped out. He was dressed to look like a free black sailor, wearing a tarpaulin hat and a red shirt with a black cravat tied up around his neck. He chose not to buy a ticket in advance, fearing that an agent in a ticket window might have extra time to inspect
his less-than-perfect papers. Instead, he had a black friend appear at the very last second with all of his luggage so that he would have an excuse for boarding the train in a last-second frenzy.
There were no Jim Crow laws back in slavery times. The car Fred hopped aboard was no doubt full of both blacks and whites. The moment Fred had been dreading arrived when a ticket taker appeared, making his way down the aisle.
The heart of no fox or deer, with hungry hounds on his trail, in full chase, could have beaten more anxiously or noisily than did mine.
By federal law, train companies back then could be held liable if they failed to take steps to identify runaway slaves. These laws worked in the same way as modern-day rules governing the sale of liquor and cigarettes to minors. The moment of truth arrived:
“I suppose you have your free papers.”
“No sir, I never carry my free papers to sea.”
“But you have something to show you are a free man, have you not?”
“Yes, sir! I have a paper with the American eagle on it that will carry me around the world!”
Fred tried to deliver his lines with a patriotic flourish. The conductor barely glanced at his papers, taking the money for his fare to Wilmington and then moving on.
It Almost Went Wrong in Havre de Grace
This brings us to Havre de Grace, the postcard-pretty town you might visit when thinking about this story. It lies along the railroad route between Baltimore and Wilmington. Technically speaking, the town isn’t on the Delmarva Peninsula, but it does brush right up against the edge of the Eastern Shore. Including this “harbor of grace” as the destination for this chapter allows me to include a really important story in this book. Plus, it gives you the chance to spend some quality time in a town full of history and charm.
On the day Fred Bailey passed through in 1838, he was presumably too preoccupied to pay attention to his surroundings. The stately old Concord Point Lighthouse dates to 1827, so it was here that day. The light ran on whale oil back then. There are little museums you can visit while in town that are dedicated to maritime history, waterfowl hunting, and a canal that was under construction when Douglass passed through. It would open for business two years later, in 1840.
A steamboat from the mid-1800s
Do you remember those funny Southwest Airlines commercials in which one important moment in life or another goes horribly awry and the tagline is, “Wanna get away?” That’s the sort of moment Fred Bailey endured here in Havre de Grace, where everyone had to get off the train and board a ferry that would take them across the Susquehanna River. There, they would board another train for the second leg of the journey.
In a dreadful coincidence, one of the workers on that ferry turned out to be an old acquaintance of Fred’s—a black man named Nichols. To make matters worse, this man saw through Fred’s disguise and proceeded to greet his old friend loudly, and by name. He asked Fred where he was going. He asked why in the world he was dressed up in such a silly sailor’s costume.
[Nichols] came very near to betraying me.… I got away from my old and inconvenient acquaintance as soon as I could decently do so, and went to another part of the boat.
Two more near misses followed that encounter. As he got ready to board his train car for the second leg of the journey to Wilmington, Fred looked up into the window of a train that had arrived at the ferry stop from the opposite direction and saw a supervisor at one of the shipyards where Fred worked. If that supervisor had looked out the window at that moment, he would have recognized Fred in an instant.
Then, once on board, Fred found himself sharing a car with another white man he recognized from the shipyards, a German blacksmith.
[He] looked at me very intently, as if he thought he had seen me somewhere before in his travels. I really believe he knew me, but had no heart to betray me. At any rate, he saw me escaping and held his peace.
It’s interesting to ponder how history might have changed if any one of those three close calls had taken a turn for the worse. But they didn’t, of course, and once Fred made it through Havre de Grace, the rest of his journey was smooth sailing.
Freedom in New York City
New York City in about 1840
He reached New York City on September 4 and immediately sent word back to Anna in Baltimore. The two were married on September 15 in a ceremony officiated by another escaped slave, Rev. James Pennington. Fred and Anna thought about adopting the last name of Johnson, but settled instead on Douglass. Later, Douglass would explain that he kept his first name so as “to preserve a sense of my identity.”
In the years that followed, after he had become a famous anti-slavery orator capable of drawing overflow crowds into churches and auditoriums all over the North, Frederick Douglass would sometimes step on stage and begin his remarks with these words:
I appear before you this evening as a thief and a robber. I stole this head, these limbs, this body from my master and ran off with them.
TESTIMONY: ‘The Loneliness Overcame Me’
Author’s Note: At the end of every chapter in Tubman Travels is an afternote section which features voices from slavery times, speaking of their experiences in words from those days.
In the days after he made his way to freedom, Frederick Douglass found himself on an emotional roller-coaster ride that started at the peak of elation but soon descended into the depths of loneliness and uncertainty. Interestingly, the experience he describes in Narrative of the Life of Frederick Douglass echoes quite closely the emotional journey that Harriet Tubman would go through in the wake of her own run to freedom 11 years later.
Here is Douglass:
I have been frequently asked how I felt when I found myself in a free State. I have never been able to answer the question with any satisfaction to myself. It was a moment of the highest excitement I ever experienced. I suppose I felt as one may imagine the unarmed mariner to feel when he is rescued by a friendly man-of-war from the pursuit of a pirate. In writing to a dear friend, immediately after my arrival at New York, I said I felt like one who had escaped a den of hungry lions.
This state of mind, however, very soon subsided; and I was again seized with a feeling of great insecurity and loneliness. I was yet liable to be taken back, and subjected to all the tortures of slavery. This in itself was enough to damp the ardor of my enthusiasm. But the loneliness overcame me. There I was in the midst of thousands, and yet a perfect stranger; without home and without friends, in the midst of thousands of my own brethren—children of a common Father, and yet I dared not to unfold to any one of them my sad condition.
I was afraid to speak to any one for fear of speaking to the wrong one.… The motto which I adopted when I started from slavery was this—“Trust no man!” I saw in every white man an enemy, and in almost every colored man cause for distrust. It was a most painful situation; and, to understand it, one must needs experience it, or imagine himself in similar circumstances.
Thank you for reading this excerpt. Here, again is where to find Tubman Travels and my other books.
–posted by Jim Duffy for Whimbrel Creations/Secrets of the Eastern Shore in August 2025. All rights reserved.
