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This is an excerpt from Tubman Travels: 32 Underground Railroad Journeys on Delmarva. More info about the book is here.

Standing in downtown St. Michaels today, with its tourist-friendly bevy of upscale shops and interesting eateries, it’s not easy to imagine the sort of place this town was when Frederick Douglass arrived from Baltimore in the early 1830s. Still known as Fred Bailey then, he was at this point a city boy through and through. He was horrified to find himself stuck in a rural backwater on Maryland’s Eastern Shore.

Fred lived smack dab in the heart of downtown St. Michaels, near where Talbot Street, the main drag, intersects with Mill Street. There is a historic marker near that intersection, though no one knows precisely where the home of Thomas and Rowena Auld stood in this vicinity. The Aulds were a reasonably prominent family in the community. Thomas operated a store out of the front part of their house. He also served as the town’s postmaster.

THE CRIME: Teaching Blacks to Read

Whether through Fred’s own boasting or by some other means, word soon got out among the blacks of St. Michaels that this newly arrived teen knew how to read and write. In Baltimore, Thomas Auld’s sister-in-law, Sophia, had taught Fred a few basics about the alphabet. Fred then used his own smarts and creativity to parlay that smidgeon of knowledge into full-fledged literacy.

Here in St. Michaels, a man named Wilson asked Fred if he would teach some of the local blacks to read. Together, the two of them set about scavenging for some discarded old books and school texts that Fred could use in a makeshift classroom. One Sunday shortly thereafter, some 20 students gathered in the home of a free black man, James Mitchell. They didn’t try very hard to keep this session a secret. They were operating under the assumption that there was nothing illegal about blacks learning to read. The next weekend, Fred and his students would find out otherwise.

There were quite a few reasons why many whites back then didn’t want blacks to read. They feared literate blacks might be corrupted by all the abolitionist “propaganda” going around. They worried that runaway slaves might be able to forge free papers and travel passes.

Back up in Baltimore, when Hugh Auld had ordered his wife to stop teaching Fred the letters of the alphabet, he had said this:

A nigger should know nothing but to obey his master—to do as he is told to do. Learning would spoil the best nigger in the world. … [T]here would be no keeping him. It would forever unfit him to be a slave. … [And] it could do him … a great deal of harm. It would make him discontented and unhappy.

Many white folks in St. Michaels, then regarded the news of these reading classes as a threat. That next Sunday, a mob of whites armed with clubs and other weapons broke up the class. They claimed the authority of a 1723 law that prohibited “tumultuous meetings of slaves.”

THE PUNISHMENT: Exile to Covey Farm

This turn of events put Thomas Auld in a difficult spot. A shopkeeper’s livelihood depends on the goodwill of his customers, and many of those customers were now watching closely to see how Auld would handle this new slave who had showed up from the big city and commenced trying to teach “their” blacks to read.

Auld did not disappoint those neighbors. He hired Fred out for a one-year term to a farmer named Edward Covey, who had built a reputation for beating the rebelliousness out of even the most difficult slaves.

No doubt Fred was aware of Covey’s reputation on New Year’s Day, 1834, when he set off from the corner of Cherry and Talbot streets on the long seven-mile walk to his new home. You can trace Fred’s steps today by following Route 33 out of town and into the countryside, passing first the turnoff for Neavitt and then the one for Claiborne, and then continuing right on through the little outpost of McDaniel until you come to New St. John’s United Methodist Church on the left.

The Covey Farm is just across the road from here, on the Chesapeake Bay side. The land is private, so you can’t go wandering about. There is nothing left of the Covey farmhouse and outbuildings in any case. In fact, those structures most likely stood on land that is now under water due to the one-two-three punch of erosion, subsidence, and rising sea levels.

Covey was 28 years old on that New Year’s Day when Fred arrived. He stood 5 feet, 10 inches tall. His most notable features were a short neck, a “wolfish” face, and a voice that emerged from the side of his mouth in “a sort of light growl, like a dog, when an attempt is made to take a bone from him.”

There were only three other slaves working on the small Covey farm, so there was no place for Fred to hide. To make matters worse, he had never worked as a field hand. Covey quickly set out to make a fool of Fred. He sent the newly arrived city boy out one day to chop some wood. The next, he gave him a wagon and a team of oxen so he could go fetch those bundles of chopped wood.

Fred went off that second day with no understanding of how hard it can be to manage a few thousand pounds of oxen. The beasts ran wild on him twice. After the first accident, Fred was able to put the pieces of his broken wagon back together. The second time, however, the oxen busted through a fence on Covey Farm, where the master soon discovered that a gate had been damaged because of Fred’s lousy driving.

Covey whipped Fred for that.

Fred received quite a few more whippings in the days and weeks that followed. Covey was a devious, obsessive overseer, always popping up out of the blue at the most unexpected times in hopes of catching a slave slacking off or making a mistake.

He was under every tree, behind every stump, in every bush, and at every window on the plantation.

By midsummer, Fred’s spirit was beaten. It might well have been the lowest point of his life.

I was broken in body, soul, and spirit. My natural elasticity was crushed, my intellect languished, the disposition to read departed, the cheerful spark that lingered about my eye died; the dark night of slavery closed in upon me; and behold a man transformed into a brute!

This bleak period found him gazing out toward the Chesapeake Bay on occasion, feeling great jealousy as the sails of passing vessels blew free in the distance. He was trying in those moments to hold onto the dream that he, too, might find a way to freedom, but the notion was slipping fast from his mind.

CONCLUSION: The Fight of His Life

Tubman Travels: 32 Underground Railroad Journeys on DelmarvaThe Covey Farm nightmare came to a head during wheat-threshing season in August. Fred was hard at work in the fields one day when he collapsed, presumably suffering from heat stroke. Covey was having none of it. He kicked Fred’s prone body and screamed at him to get up and get back to work.

When he finally came to, Fred made a run for it—not towards freedom, but back to St. Michaels where he might be able to plead for mercy from his owner, Thomas Auld. Auld listened to Fred’s story, then ordered him to get out and walk those seven miles right back to Covey Farm.

Fred didn’t return right away. He spent a desperate night in the woods, without food. An older black couple took him in. The man’s name was Sandy, and he had managed to keep hold of his African folkways even after most of a lifetime in American slavery. Sandy dug up a root in the woods and promised Fred that it would protect him as long as he kept it in his right-hand pocket.

It was a Sunday when Fred showed up back at Covey Farm. For all his idle cruelty six days a week, Covey was a devout and careful observer of the Christian Sabbath. There would be no discipline on Fred’s first day back.

Monday morning was a different story, however. Covey sent Fred into the horse stables and then set upon him in fury. He grabbed Fred by one leg and threw him to the ground. He tried to spin a noose around both of Fred’s legs, but Fred scooted clear.

“Do you mean to resist, you scoundrel?”

“Yes, sir!”

Even much later in life, Fred could not really fathom “whence came the daring spirit.”

Could the fight really have lasted two hours? That’s how long the two men wrestled in Fred’s memory many years later, in any case. Their battle spilled out of the stable and into the yard, where Covey demanded that another slave help him subdue the teenager. That slave declined to step in:

“My master hired me here to work, and not to help you whip Frederick.”

It was Covey who broke off the battle and walked away, declaring victory and boasting to Fred about what would happen on their next go-round. But everyone who saw the fight knew that Covey had not won at all. He had not drawn even a drop of blood. He had not managed even one clear swing with his whip.

Fred, too, knew that Covey had not won the fight, that his claims of victory were nothing but idle boasts.

What happened next is hard to fathom: The slave breaker simply let the matter drop. For the last few months of Fred’s term at the farm, Covey made no more efforts to discipline or whip him. He simply ignored Fred’s existence altogether.

Had Covey really convinced himself that he’d won the fight and that was that? Or was it more complicated? Was he now afraid of Fred? Was he backing down? Or perhaps Thomas Auld had stepped in quietly here and told Covey  to keep his hands off of Fred. There is no telling the answers to these questions. What we can say is what was going on in Fred Bailey’s mind.

I felt as I had never felt before. It was a glorious resurrection, from the tomb of slavery, to the heaven of freedom. My long-crushed spirit rose, cowardice departed, bold defiance took its place; and I now resolved that, however long I might remain a slave in form, the day had passed forever when I could be a slave in fact.


This battle with Mr. Covey was the turning point in my life as a slave. I was NOTHING before: I WAS A MAN NOW.

Fred’s time in the grip of the slave breaker came to a close on Christmas Day, 1834. At that point, the Auld family roller coaster took another surprising turn. The very same Thomas Auld who had so mercilessly sent Fred off to be broken on Covey Farm leased Fred’s services for the following year to a farmer named William Freeland, whose reputation in dealing with slaves was one of fair play and gentle treatment.

Many years later, Frederick Douglass would recall Freeland as “the best master I ever had, until I became my own master.” The time when Fred would be his own master was still quite a way off, however.

–Posted by Jim Duffy on 8/4/17

NOTE: This is an excerpt from Tubman Travels: 32 Underground Railroad Journeys on Delmarva. The chapter of the book where this story appears also includes one section on the big-picture story of Douglass’s time with the Auld family and another in which Douglass talks about how he would yearn for freedom during this period while watching the sails of passings boats on the Chesapeake Bay. There is also a collection of travel resources to help you discover interesting things to do and see while visiting St. Michaels and the surrounding area.

More information about Tubman Travels, including where you can buy a copy, is here.


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