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This is an excerpt from my book, Tubman Travels: 32 Underground Railroad Adventures on Delmarva. The book tells keystone stories about the Underground Railroad, with each story attached to place or places that you can go visit. More info about the book here.

BIG PICTURE: A Ride for the Ages

American history has its share of famous horseback rides. There is the “Midnight Ride” of Paul Revere, of course, in which the Massachusetts patriot spread the news that the British army was on the move. Then there is Delaware’s Caesar Rodney, who made a mad dash to Philadelphia so as to cast the last-minute vote that put Delaware in support of the Declaration of Independence on July 4, 1776.

If things worked a little differently in the field of history, the name of Harriet Shephard might rank on that level in the annals of the Underground Railroad. But alas, what stories we end up hearing about depends on what survives over the centuries. There are no old records, letters, account books, or court cases that have much to say about this other Harriet from the Eastern Shore of Maryland. When was she born? When did she die? Who was she married to? And what happened to her after she made her mad dash out of bondage?

STORY: The Other Harriet’s Wild Ride for Freedom

What we do know is Harriet Shephard was born into slavery somewhere in the town of Chestertown in Kent County, Maryland. We can be kinda sorta sure that her owner there was a man named George W.T. Perkins, since the census records listing the first names of Perkins’s slaves are a pretty close match with the names of Harriet and her children.

By 1855 Harriet had given birth to five children, ranging in age from newborn to about 12. Their names were Anna Maria, Edwin, Eliza Jane, Mary Ann, and John Henry.

The town those children grew up in was already thick with history. Today, Chestertown ranks as the colonial king of the Eastern Shore, as more buildings from that pre-independence era are still standing here than anywhere else in the state outside of Annapolis. There is no historic marker or specific site here that will put you in touch with the story of the Shephard family, but the sights you’ll see while strolling the town today include a good number of buildings that Harriet and her children likely walked past as well.

There seems to have been something contagious about escapes along the Underground Railroad. They came in batches, as if some runaway fever were making the rounds. I’ve touched elsewhere in these pages on the rash of runaways that had Harriet Tubman’s home turf of Dorchester County in such an uproar in the spring of 1857.

The fall of 1855 was like that here in Chestertown. One group of 10 slaves made their escape in September. Another group of seven fled on October 20.

William Still Photo

William Still

Harriet Shephard caught the fever on October 26, a Friday. We have only vague hints as to why she ran. The Underground Railroad chronicler William Still met Harriet during her escape and later recalled her saying that she had not received “kind treatment” from her master. Still also praised Harriet for a strong desire to see her children grow up free of slavery.

Harriet’s ride was a remarkable affair, even by the standards of the Underground Railroad. Not many women led their own escapes in the manner of these two Harriets, Tubman and Shephard. And there may not be any comparable case at all in which that woman was the mother of five, with all of her children in tow.

In all, there were 11 people in Harriet Shephard’s party. Seven were minors—Harriet’s five children and two enslaved teenagers, William Thomas Freeman and Thomas Jervis Gooseberry. We do not know the names of the other three, though two of them were reportedly an aunt and an uncle of Harriet’s.

Another remarkable element of this escape is its sheer brazenness. At some point in the afternoon or evening of that Friday, Harriet and her makeshift band of runaways simply absconded with two carriages and several horses from Harriet’s master.

Most of the other escape stories in this book are secretive affairs involving nighttime travel, hopscotching from one hideaway to another. Harriet and her runaways didn’t do that—they just ran, flat out and as fast as they could. While you stroll the streets of Chestertown today, put an image in your mind’s eye of that carriage and those horses flying by.

Harriet must have pushed those stolen horses to the limits of their endurance, considering that her party of 11 rolled into Wilmington, Delaware, 45 miles away, the next morning. She was there almost before the white folks back home had a chance to notice she was gone.

“It is but reasonable to suppose that the first report [of this escape in Chestertown] must have produced a shock scarcely less stunning than an earthquake…,” Still would write in his journal a few weeks later, adding a bit of speculation about the “cursings and threatenings” that likely filled the air in town when the news broke.

Harriet and her compatriots don’t seem to have had much in the way of a plan beyond running those horses as hard as they could. It’s probably safe to assume that they took the straightest possible route to Wilmington. The modern-day Route 301 is one candidate, though perhaps some other road ran along a parallel route back then.

Once in Wilmington, the 11 runaways made no effort to disguise themselves. They simply “ventured up into the heart of town in carriages, looking as innocent as if they were going to a meeting to hear an old-fashioned Southern sermon,” Still reported.

Underground Railroad Conductor Thomas Garrett

Thomas Garrett

But luck was on Harriet’s side. One or more sympathetic souls spied her party’s arrival and guessed their predicament. They got word to Underground Railroad conductor Thomas Garrett, who soon advised the runaways to simply abandon those horses and carriages right in the middle of the street.

Slave hunters arrived on the scene a few hours later, on Saturday afternoon. They found the stolen horses right away, but Harriet and her crew were another matter. By then, Garrett had the runaways in disguises and on their way north via a string of safe houses in southern Pennsylvania, first in Longwood and then in Pocopson and then in Kimberton. It was early November by the time Harriet and her children arrived in the Philadelphia office of William Still.

We don’t know what happened after that. The historians who’ve looked at the flight of Harriet Shephard speculate that she and her children were transported into upstate New York and on across the Canadian border, but no one knows for sure where they landed, or what became of them later in life.

The only fleeting mention of Harriet that appears in the historical record after her mad dash to freedom is from back in Chestertown. There, a notation in the Maryland census records from 1860 shows Harriet’s former owner reporting to the government that several of his slaves belonged in an official category called “fugitives from the state.”

In other words, they were still free.

BONUS STORY: Fortune Tellers and Perfidious Scamps

Tubman Travels: 32 Underground Railroad Journeys on DelmarvaI have not come across an estimate of how many slaves escaped from Chestertown and Kent County in the years after Harriet Shephard’s ride to freedom, but the numbers must have been significant.

In 1858, slave owners were once again up in arms over the matter of runaways. This time, they were taking the law into their own hands in a desperate, violent campaign to prevent any more of their “property” from running off.

On June 23 of that year, a stranger approached the house of James Bowers, a white, anti-slavery Quaker who had been acquitted a couple of years before on charges of aiding a runaway. That stranger asked Bowers for help with a broken-down carriage and then led him into an ambush by a group of 30 men. Bowers was soon dragged into some nearby woods, where he was tarred and feathered and then told to leave the state immediately, or else.

Bowers was forced to leave his pregnant wife behind that day. The local press branded him a “perfidious scamp” and an “evil doer.” Despite this public disparagement, Bowers returned to Kent County after the Civil War, moving onto a piece of property near the modern-day town of Worton. He is buried in a Quaker cemetery near the town of Lynch.

In the days after the Bowers ambush, Kent County’s proslavery vigilantes went after another target, a free black woman named Harriet Tillison. This woman apparently had a habit of wandering the backroads of Kent and Cecil counties, where she had earned a reputation for her skills in “conjuration and fortune telling.”

According to a local newspaper account, however, Tillison’s various comings and goings were often suspiciously “followed by the escape of slaves.” That same article describes her as “dwarfish in appearance, scarcely weighing 50 pounds,” and perhaps quite light-skinned, as if she “has a strong infusion of the Anglo-Saxon.”

This is tantalizing stuff: Was she, perhaps, a Tubman-style conductor operating on the Upper Eastern Shore? Alas, there is nothing else in the way of surviving evidence about her. All we know is that Tillison, too, was tarred and feathered by that mob. There is no definitive record of what became of her after that.


• Downtown Chestertown is full of shops, restaurants, parks, and other amenities. Information for visitors is available from the Downtown Chestertown Association.

• Information about things to do both in Chestertown and throughout Kent County is available from Kent County Tourism. The tourism department operates the Kent County Visitor Center at 122 North Cross Street in Chestertown, 410.778.0416.

–posted by Jim Duffy on March 4, 2021 and updated in September 2023 for Secrets of the Eastern Shore/Whimbrel Creations LLC. All rights reserved. The content is an excerpt from the book Tubman Travels: 32 Underground Railroad Adventures on Delmarva.





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