Skip to main content


This is an excerpt from my book, Tubman Travels: 32 Underground Railroad Journeys on Delmarva. The book first came out in 2017. I released an updated version here in 2022. More info about the book here.

BIG PICTURE: Where Slavery Meets Sadism

If a movie ever gets made about the life of Isaac Mason, it would need to be done by a director who comes to the project half-crazy to begin with—Quentin Tarantino say, or better yet, one of those twisted South Korean directors who are always shifting from sadistic horror to slapstick comedy in the blink of an eye.

At times, the stories that Mason tells in his autobiography are quite excruciating. His journey, like so many others along the Underground Railroad, started from a place of powerlessness. Usually, the situations that sparked slaves to make a run for freedom had some semblance of logic about them. A farmer in need of money decides to sell his “property” at the auction block. An overseer determined to keep his charges in line relies too heavily on the whip.
Isaac Mason’s story is in another category of powerlessness altogether, one that is all the more surreal and terrifying for the sheer randomness of its violence.

STORY: ‘We All Knelt Down on the Snow-Covered Ground’

Mason was born in 1822 in the town of George Town Cross Roads, on Maryland’s Upper Eastern Shore. Today, that town is called Galena. It had 500 residents in Mason’s day. It has 600 residents now.

The town is just off Route 301, the pretty four-lane highway that runs between Kent Island in Maryland and Wilmington in Delaware. Downtown Galena is a tiny, quiet affair, but interesting. There are a couple of places to enjoy down-home food, a couple of antiques shops, and an interesting grocery store that specializes in healthy foods.

North of town, Main Street changes its name to Augustine Herman Highway en route to the town of Georgetown, on the Sassafras River. That’s the direction you’ll find Toal Park on the right-hand side, a little way outside of Galena. The entrance to the park is a nondescript affair; it looks like a facility that will be of interest only to the families of Little League kids, but if you drive all the way to the tree line in back, you will find your way to a hilly little stroll through some woods with intermittent water views—a perfect setting for giving some thought to days gone by and the strange saga of Isaac Mason.

He was the oldest of five siblings. His enslaved mother, Sophia, worked as a housemaid for her owner, a widow named Hannah Woodland. His free father, Zekiel, helped run the Woodland family farm. All seems to have been relatively calm with Isaac’s young life until the age of 13, at which point Hannah Woodland passed away.

In time, her estate sold the farm (and young Isaac, and his mother) to a man named Isaac Taylor. Somewhere in the transition, Mason’s family watched one of its elders endure a casual bit of cruelty that was all too common in slavery times:

My grandfather, in consideration of his old age and the time being past for useful labor, was handsomely rewarded with his freedom, an old horse called the “old bay horse”—which was also past the stage of usefulness—and an old cart; but, alas! no home to live in or a place to shelter his head from the storm.

This new owner rented the teenaged Isaac out to a family with the name of Hyde. All went reasonably well there until the day when Isaac returned from a rabbit-hunting expedition with friends and entered the kitchen on one of his routine chores, fetching a milk pail.

For no apparent reason, Mrs. Hyde locked the kitchen door behind him and ordered him to remove some of his clothing. Then she commenced whipping him with “well roasted hickory wottels.” Mason endured it for a time, but then resisted, pushing Mrs. Hyde aside and jumping out a window.

He hid out for a while, first with his mother and then with the aforementioned grandfather. When things calmed down and Mason was able to show his face again, he was rented out to a different family, the Wallises. They in turn assigned him to work for a cabinetmaker and casket-maker, James Mansfield, who lived just outside of nearby Chestertown in a building occupied as of this writing by the nonprofit Kent Cultural Alliance.

Mason promised this new master that he would be a good slave. Mr. Mansfield seemed pleased with his new hire.

I got along for the first two weeks very nicely.… I concluded I was all right and was going to have a nice time at my new home. At this time there was not the dread of a daily whipping and the loss of one meal a day. It was not long before I was to learn that storms followed calms, and war came after peace.

One Friday morning about four weeks into his new assignment, Mason’s new mistress, Mary Mansfield, approached and asked him what he was working on.

[H]er face was awfully red; there was something wrong but I could not divine it. She hurriedly went out of the room where I was, into the back room, and got her cowhide; without the least ceremony she lit on me—the same as a hungry hawk on an innocent chicken.

Mason begged her to stop, but she kept at it even as blood streamed from his head and back. She relented only when she herself was overcome by exhaustion. Mason had no idea what, if anything, he had done wrong.

Isaac Mason Underground Railroad

Isaac Mason

Then things got really weird. Mary Mansfield never raised a whip against Isaac again. Instead, she demanded that her husband do the deed on a regular basis while she watched. James Mansfield did not have a reputation as a gentle sort of slave owner, but the sick nature of this ritual proved too much even for him. Mason overheard James tell his wife one day that “he would not do it any more to gratify her.”

Mansfield eventually moved young Mason away from his home, and from Mrs. Mansfield. He assigned Isaac to work on farmland outside of town and had him work as well on the casket-making end of his business, transporting dead bodies to cemeteries.

On one occasion I went to bury the wife of a high sheriff, and to my surprise and confusion found that all the men were drunk. When they arrived at the burying ground they were just fit for business—not to bury, but to quarrel.

Those men proceeded to drop the casket while pulling it off of the wagon that served as a hearse. See what I mean about the need for a little slapstick comedy in the midst of that potential horror movie about Mason’s time in slavery? Not knowing what would happen next, Mason fled the scene and returned to the Mansfield farm.

He worked five years on that farm and never once got whipped. While on a business trip with his master to Baltimore, however, Mason found himself alone with a bit of free time and decided to walk the streets of the city. Two white strangers beat him savagely for the offense of walking between them on a sidewalk instead of circling around them by way of the street. Even Mason’s master had no idea that this rule existed in the city.

Back in Kent County, things went completely off the rails. When Mary Mansfield gave birth to a child, a neighbor came calling to mark the occasion and help out with chores. Mason was back at the house on this day, and so he was there when this woman served plates full of rotten meat to the slaves. Mason gave his share to some dogs.

Seeing this, the woman decided that it was some sort of terrible offense against her. She demanded that Mason be punished. James Mansfield began beating Mason with a stick. The slave fought back, pushing his master over a pile of wood. Mansfield called for his gun. Mason fled, leaping over one fence and making his way toward a second one.

As I ascended the second fence … he aimed his gun, firing three shots at me. The first shot grazed my head, removing a little hair; the second touched my ear, and the third passed through my hat; but they did not stop me from running.

Again, Isaac Mason went into hiding. Mansfield eventually sent word out through the grapevine of slaves and free blacks that everything would be fine if he returned to the farm. He did, but things were not fine at all. The woman who had served up that rotten meat was a member of the Wallis family, which was renting Mason out to the Mansfields. Her father, Hugh Wallis, saw Mason one day and commenced, out of the blue, beating him with a pitchfork.

It was around this time that Mason heard rumors that he was about to be sold to a slave trader from New Orleans. He decided that he had no choice but to run. He talked two fellow slaves into joining him on the journey.

Mason planned his escape carefully, working out the details during a meeting with a free black Underground Railroad conductor in George Town Cross Roads named Joe Brown. They set a rendezvous for Brown’s cabin one night the following week. The price of transit would be $9. But this is what Mason and his compatriots found when they showed up at Brown’s house at the appointed time:

To the horror of all we found Joe lying on the floor dead drunk. Joshua and George did not know Brown’s failings; they became alarmed at the situation and talked strongly about going back home.

Mason convinced his companions to stick it out for one more day. Mason’s mother lived nearby. The trio hid in the attic at her place until Brown emerged from his stupor the next afternoon. Snow covered the ground when they set out that evening on the walk to Wilmington, Delaware, 35 miles away.

They got within eight miles of their destination when Brown called the march to a halt. He told his passengers to hide in a wooded area and wait for him to return and fetch them. In the woods, the trio found a seemingly perfect bit of shelter, a gigantic white oak that had fallen to the ground so recently that it was still full of foliage.

Fox Hunt 1800s from painting by John Nost Sartorius Tate Gallery

A fox hunting scene from the 1800s by artist John Nost Sartorius (Tate Galleries, London)

Shortly after daybreak, Mason found himself enduring another round of slapstick comedy. He and his friends heard the baying of fox-hounds in the distance. As that sound grew closer, they spied a party of white hunters on horseback, riding in after the hounds. The fox that those hounds were trailing was desperate to return to the safety of its home.

To my great astonishment, I discovered that we were lying over the hole that led to the reynard’s den. He made two or three attempts to get into the hole but we succeeded in beating him off.

The hunters stayed in the vicinity for much of the day, but somehow never discovered the runaways. When darkness came at last, Mason decided to give up on his missing conductor, who had been gone almost a whole day by this point. Mason located the North Star up in the sky, remembering how an old man had once told him that the “Lord had placed it there to lead people out of slavery.”

The Snow-Covered Ground, as depicted by the painter Claude Monet in The Magpie collection of Musée d'Orsay

The Snow-Covered Ground, as depicted by the painter Claude Monet in The Magpie (Musée d’Orsay)

Five miles into this leg of their journey, they ran smack dab into Joe Brown. He gave the famished runaways some food, then handed them off to an elderly man Mason had never seen before.

There are a great many venturesome things a man will do, when determined to escape from danger or an evil, that he would not do when otherwise situated. To think that we had placed our fate in the hands of a man who was, to us, an utter stranger. … The experience of the past had taught us the lesson to trust and go forward, and forward we went.

Mason had lost track of what month it was, but he kept up with the days of the week. He knew that it was a Tuesday “when our eyes rested on [the state of Pennsylvania,] where liberty for the negro slave could be enjoyed.” Mason asked that stranger of a conductor if it would be all right to pause there and say a prayer.

The old man readily consented to the proposal, and we all knelt down on the snow-covered ground and offered up humble thanksgiving, and petitions for future protection and guidance, to the Great Supreme Ruler of heaven and earth.

Amen, Mr. Mason.

POSTSCRIPT: A ‘Premature Graveyard’

Even in freedom, Isaac Mason continued to endure one close call after another. He initially settled on a farm in Pennsylvania, where he met a woman he planned to marry. Those plans were put on hold, however, when slave catchers from his native Kent County appeared in the area and kidnapped another former slave from a neighboring farm.

Mason went back on the run at that point. He did marry that woman eventually, and they settled in Philadelphia. But then, in another turn of slapstick coincidence, he crossed paths one day with a member of the dreaded Wallis family and ended up on the run yet again. He went to Boston this time, and then joined the larger black exodus to Canada that greeted the passage of the Fugitive Slave Act of 1850.

A decade later, Mason signed on to join a group of blacks who had been recruited to leave the country and establish a new settlement on the island of Haiti. He had high hopes at the time of his departure, but nearly died in the storms his ship encountered en route. His experiences on the island amounted to nothing but disaster and disappointment. In the end, he came to regard the whole scheme to encourage the emigration of blacks out of the country as nothing but a “premature graveyard.”

He finally ended up in Worcester, Massachusetts. It was there, he decided, that “I should dwell until the end of my days.” He was in his 70s when he published his memoir. No one seems to know for sure when he died. I hope and trust that he passed away in the comfort of the home he had found at long last.


Galena is in Kent County, as is the nearby town of Georgetown. Information about things to do in both of those towns as well as the surrounding countryside is available from Kent County Tourism.
• Kent County Visitor Center, 122 North Cross Street, Chestertown, Maryland
•; 410.778.0416

–written by Jim Duffy for the book Tubman Travels: 32 Underground Railroad Journeys on Delmarva, which is published by Secrets of the Eastern Shore for Whimbrel Creations LLC. All rights reserved. More info on all of the Secrets of the Eastern Shore books here.

Leave a Reply