Skip to main content


This excerpt from the Secrets of the Eastern Shore book, Tubman Travels: 32 Underground Railroad Journeys on Delmarva, tells the story of Harriet Tubman’s own run for freedom in September of 1849.  More information about the book, including where to buy it in stores and online, is available here.

BIG PICTURE: Strangers in a Strange Land

The first time I went looking for Red Bridges Road in Greensboro, Maryland, I got lost. I had checked Google Maps in advance, but my eye went straight to the line for a Red Bridges Road on the east side of the Choptank River, and I ended up wasting quite a bit of time roaming up and down Draper’s Mill Road when I should have been on the west side of the river, along Greensboro Road.

It was a minor mishap, of course. This is the 21st century. I had a smart phone. I had plenty of gas. The nearby town of Greensboro is full of friendly folks who will happily help out a stranger.

I found my way soon enough to the right place, a little park hidden away at the end of a winding dirt road. Historians recommend a visit to Red Bridges because it’s the kind of place where runaways might have crossed the Choptank River. The river isn’t two miles wide here, like it is down in Cambridge. It’s more of a creek, actually. You can stand on its banks here and imagine splashing across under the cover of darkness and ending up soaked only up to your thighs.

But my little mishap on the way there left me with another question: How would a slave in the 1840s know how to reach this spot? Some had conductors to guide them, of course. But oftentimes slaves ran away in complete ignorance of the simplest matters of geography: Where in the world is Pennsylvania? How far away is it? What towns lie along the way? What rivers need crossing?

This is, in fact, the state that Harriet Tubman seems to have been in on her first run for freedom. She and a couple of her brothers left without a conductor, or even much of a plan. They just started wandering north.

Standing with a cup of coffee on the banks of the Choptank at Red Bridges one winter morning, I tried to come up with a way to imagine their predicament. The best I could do was to imagine myself on the run from the powers that be in a foreign land. I picked the steppes of central Asia, actually, in the time of Genghis Khan and the Mongols.

I pictured in my mind’s eye the way that vast landscape might look in the dark of night. Then I got to asking obvious things: What if heavy clouds obscured my view of a guiding star? What if the moon was too bright, making it hard to stay out of sight? What would I do if and when some wide, impassible river forced me to steer away from that guiding star? Was that the baying of bloodhounds I heard in the distance?

I had no map and no road signs and no cell phone. I imagined that the strangers in nearby towns were more likely to be dangerous foes than friendly souls. Would I have pressed on? Or would I have played it safe and turned back?

STORY: ‘I’m Sorry I’m Gwine to Lebe You’

As the summer of 1849 drew to a close, Harriet Tubman made the decision to run. Rumors were flying in the wake of her owner’s recent death about the imminent sale of some of his slaves in order to pay off some of his debts. Tubman was not the sort of woman who was going to wait around in such circumstances. Those recurring dreams she had in which evil horsemen kept swooping down on her were only getting more intense.

Liberty or death: She would have one or the other.

In mid-September, she convinced at least two and perhaps three of her brothers to join her in the flight to freedom. By the standards of most other slaves on the Eastern Shore, this was a reasonably worldly bunch. They knew their way around the shipyards in Madison. They had probably heard quite a bit through the Underground Railroad grapevine about the lay of the land and the turns in the river on the way north.

But they seem to have set off with no real preparation beyond wishful thinking. There is no indication that Tubman and her brothers ever made it all the way up to Red Bridges on this trip, but the point of setting this chapter at this particular spot is that it’s the kind of place they needed to be able to find.

All they had, however, were those strange dreams and visions in Tubman’s head, and perhaps that North Star up in the sky, if it wasn’t too cloudy. According to the biographer Sarah Bradford, that first escape attempt ended this way:

[T]hey had not gone far when the brothers, appalled by the dangers before and behind them, determined to go back, and in spite of her remonstrances, dragged her with them.

Knowing what we now know about how Harriet Tubman’s story turned out, it’s easy to jump to the conclusion that those brothers made a dumb decision. They were going back to a life in slavery and even, God forbid, the risk of getting sold off away from their family and loved ones.

But what if the brothers were right? What if their sister wasn’t actually ready that first time out? What if she needed this sort of miserable failure in order to become the famed “Moses” of her people? If she and her brothers had gotten caught on that first blind flight, would Tubman ever have gotten the chance to cross into freedom?

The actions Tubman took after returning home from this failure imply that deep down she knew that her brothers had a point. She reached out quietly to the Underground Railroad network, telling a white neighbor about her situation, and about her plans to run.

No one knows for sure who that mysterious woman was, but the speculation centers on Hannah Leverton, a Quaker woman who lived with her husband, Jacob, outside of modern-day Preston and just a few miles away from the cabin of Tubman’s parents on Poplar Neck.

In any case, the white woman gave Tubman a slip of paper with two names written on it. She also must have provided Tubman with directions to the first station on her journey. Tubman was so filled with gratitude toward this woman that she gave her a hand-stitched quilt as a gift.

It was only a few days after she and her brothers returned that Tubman decided to set out on her own, perhaps after hearing another rumor that she herself was headed to the auction block. She did not say goodbye to her mother. Instead, she offered to take on her mother’s chore of milking cows so that Rit could quit working a little early that day and relax.

Tubman did seek out a friend named Mary, finding her in the kitchen of the home of slave owner Anthony C. Thompson, who owned much of the forestland on Poplar Neck. The room was too crowded with people for a private conversation, so Harriet coaxed Mary outside in hopes of finding a little privacy, but then Thompson himself rode up on a horse and Mary scurried back inside at the sight of him.

Tubman then stood outside and sang a song of farewell to Mary:

I’m sorry I’m gwine to lebe you,
Farewell, oh farewell;
But I’ll meet you in the mornin’,
Farewell, oh farewell.
I’ll meet you in the mornin’.
I’m boun’ for de promised land,
On the other side of Jordan,
Boun’ for de promised land.

And she was off, alone this time. When she found her way to that first station and showed off the piece of paper with two names on it, the woman of the house told Tubman to grab a broom and start sweeping up. Tubman caught on quickly—this was a cover so that passersby or neighbors wouldn’t get suspicious. Sometime after dark, that woman’s husband told Harriet to climb into the bottom of his wagon. He then piled that wagon with enough supplies so that his human cargo would not be seen.

And that’s it. We don’t really know what happened after she got in that wagon. What other stations did she stop at? Which conductors helped her? Did she have any close calls? All we really know is that she was in Philadelphia soon enough.

Later, Tubman would describe her feelings at the end of this journey as a mix of elation and loneliness. What about her family back in Maryland?

To dis solemn resolution I came; I was free, and dey should be free also; I would make a home for dem in de North, and de Lord helping me, I would bring dem all dere. Oh, how I prayed den, lying all alone on the cold, damp ground: “Oh, dear Lord,” I said, “I haint got any friend but you. Come to my help, Lord.”


TESTIMONY: ‘Gloom and Melancholy Spread Through My Soul’

James Pennington

James Pennington

We have no way of knowing today exactly what happened on Tubman’s first run to freedom, the one that ended with her brothers insisting that they give up and return home. But they may have endured the sort of anguish that James Pennington went through on the first night of his run to freedom. This is from his autobiography, The Fugitive Blacksmith or, Events in the History of James W. C. Pennington, Pastor of a Presbyterian Church, New York, Formerly a Slave in the State of Maryland, United States.

I now found myself under cover of night, a solitary wanderer from home and friends; my only guide was the North Star, by this I knew my general course northward, but at what point I should strike [Pennsylvania], or when and where I should find a friend, I knew not.

The night was fine for the season, and passed on with little interruption for want of strength, until, about three o’clock in the morning, I began to feel the chilling effects of the dew. At this moment, gloom and melancholy again spread through my whole soul. The prospect of utter destitution which threatened me was more than I could bear, and my heart began to melt.

What substance is there in a piece of dry Indian bread; what nourishment is there in it to warm the nerves of one already chilled to the heart? Will this afford a sufficient sustenance after the toil of the night?

But while these thoughts were agitating my mind, the day dawned upon me, in the midst of an open extent of country, where the only shelter I could find, without risking my travel by daylight, was a corn shock, but a few hundred yards from the road, and here I must pass my first day out. The day was an unhappy one; my hiding-place was extremely precarious. I had to sit in a squatting position the whole day, without the least chance to rest. But, besides this, my scanty pittance did not afford me that nourishment which my hard night’s travel needed.

Night came again to my relief, and I sallied forth to pursue my journey. By this time, not a crumb of my crust remained, and I was hungry and began to feel the desperation of distress. As I traveled I felt my strength failing and my spirits wavered; my mind was in a deep and melancholy dream. It was cloudy; I could not see my star, and I had serious misgivings about my course.

–written by Jim Duffy; posted on Sept. 12, 2019

–Copyright Secrets of the Eastern Shore/Whimbrel Creations LLC. All rights reserved.

This is an excerpt Tubman Travels: 32 Underground Railroad Journeys on Delmarva. Learn more about the book, including where to buy a copy, here. The artwork up top here is by Lisa Krentel and appears on the cover of the book.

NOTES: Travel Resources & Info

(1) The crossing at Red Bridges is part of Christian Park, which is on Red Bridges Road just north of Greensboro along Greensboro Road. There are no amenities of note at this isolated little park, but it is a beautiful spot for a shady stroll along the banks of the Choptank in one of its skinniest stretches.

  • 26041 Red Bridges Road, Greensboro, Maryland
  • 410.479.8120

(2) Information about things to do and places to go here in Caroline County is available from Caroline County Tourism.

(3) The Harriet Tubman Underground Railroad Byway runs through both Dorchester and Caroline counties in Maryland and then on into Delaware.

• Maryland:;; 410.228.1000

• Delaware:

Leave a Reply