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This is an excerpt from a chapter in my book, Tubman Travels: 32 Underground Railroad Journeys on Delmarva. The book tells true-life tales of brave souls who made their way to freedom during slavery times on the Delmarva Peninsula. Frederick Douglass and Harriet Tubman are here. So, too, are many other, lesser-known heroes. The book not only tells their stories–it helps modern-day travelers follow in their footsteps. More info on the book here.

Young Fred Bailey got his first taste of freedom when he was still too young to understand that a thing such as slavery existed. Later in life, he would describe the freewheeling nature of his first few years by comparing the life of a hypothetical slave child with that of a white counterpart:

[The slave child] seldom has to listen to lectures on propriety of behavior, or on anything else. He is never chided for handling his little knife and fork improperly or awkwardly, for he uses none. He is never reprimanded for soiling the table-cloth, for he takes his meals on the clay floor. He never has the misfortune, in his games or sports, of soiling or tearing his clothes, for he has almost none to soil or tear. He is never expected to act like a nice little gentleman, for he is only a rude little slave. …

He literally runs wild; he has no pretty little verse to learn in the nursery, no nice little speeches to make for aunts, uncles, or cousins, to show how smart he is, and if he can only manage to keep out of the way of the heavy feet and fists of the older slave boys, he may trot on, in his joyous and roguish tricks, as happy as any little heathen under the palm trees of Africa. …

In a word, he is, for the most part of the first eight years of his life, a spirited, joyous, uproarious, and happy boy.

Little Fred passed these carefree if poverty-stricken years at Holme Hill, a farm in the countryside below the modern-day town of Queen Anne, Maryland. Historians place that site a little way southeast of the current intersection of Lewistown and Tappers Corner roads, but there is nothing really to see there today. The farmhouse of Fred’s owner, Aaron Anthony, is gone. So is the cabin where Fred lived with his free grandfather, Isaac Bailey, and his enslaved grandmother, Betsy. The land is all privately owned in any case, so there is no opportunity to get out of a car and wander around.

For a taste of the freedom that young Fred Bailey enjoyed, I would recommend instead a visit to either Tuckahoe State Park or Adkins Arboretum, or both. In these adjacent parks a little bit north of Queen Anne, you’ll still be able to take in the beauty of Tuckahoe Creek and wander the nearby woods and streams. It will be easy there to imagine the life of a little boy in the 1830s who spends pretty much all of his time wandering this paradise in search of fun and adventure. Here, too, it will be easy to picture a little cabin in the woods:

The old cabin, with its rail floor and rail bedsteads upstairs, and its clay floor downstairs and its dirt chimney and windowless sides … and that most curious piece of workmanship, … the ladder stairway, and the hole curiously dug in front of the fireplace, beneath which grandmammy placed the sweet potatoes in to keep them from the frosts, was MY HOME—the only home I ever had; and I loved it, and all connected with it.

Douglass did not recall spending much time in those years with his mother. She was always off working somewhere or another. He was too young at this point to be curious about the fact that his skin color was several shades lighter than hers, a fact that has long stoked speculation—still unconfirmed, as far as I can tell—that he was the son of his owner.

Slowly but surely Fred started to get a sense for the ways of the world, including the notion that the freedom he enjoyed in those early years would be a short-lived affair. He heard about his older siblings, for instance, but he had never met them—they were all off at some faraway place called Wye House. His master, Aaron Anthony, was there, too, working for the Lloyds as an overseer.

The Long Walk to Wye House

On a late summer day in 1824, Grandmammy Betsy packed up a few things and told Fred they were going on an adventure. At one point, Fred grew tired of walking, so 50-year-old Betsy hoisted him up on her shoulder, toting him like a “sack of wheat.” You can trace the 12-mile route they may have taken to Wye House along country backroads, meandering along Tappers Corner and then Cordova, Longwoods, Sharp, and Todd’s Corner roads before heading out towards Bruffs Island.

Fred must have been astonished at what he saw here. Wye House was a place unlike most any other on the Eastern Shore, closer to a giant Deep South plantation than to the small family farms with a handful of slaves apiece that were so much more common in the area. Grandmammy Betsy likely led Fred right past the grand entry lane reserved for white folks of the upper crust, with its elaborate ornamental gate and half-mile-long canopy of decorative trees ending at the meticulously manicured “Long Green.”

Wye House Plantation Eastern Shore Maryland

The Wye House in more modern times …

Instead, they would have taken the service road that lays a little way beyond that. It led through slave quarters that housed nearly 200 souls and had a whole city’s worth of services—icehouse, blacksmith, carpenter, shoemaker, wheelwright, shipyard, windmill, milk house, and more.

Wye House, too, is privately owned and inaccessible to the public today, so there is no opportunity here for visitors to get out and stroll the grounds. Instead, you might consider wandering by car through the backroads of the surrounding Miles Neck area. Some of the farms and estates you’ll pass have the look of old-time plantations. The small towns of Unionville and Copperville date their histories to earlier incarnations as slave quarter districts and free black communities in the time of Douglass and Tubman.

In Copperville, keep an eye out for a sign for Bailey Lane. The path it marks is just a little dirt alleyway, but the message it sends is about the deep roots that the family of Frederick Douglass has in the area—members of the Bailey clan are still living hereabouts today.

Upon arriving at Wye House after their long walk, Betsey introduced Fred to his siblings, a brother named Perry and sisters Sarah and Liza. The children all went off to play together, though Fred seems to have spent that time with his back to a wall, watching warily.

Then his grandmother was gone, headed back to Holme Hill without him. Fred howled in dismay at this realization. His brother Perry tried to console him with some fresh peaches and pears. Fred threw them to the ground and kept right on sobbing.

A Mother to the Rescue

Things did not go well for Fred at Wye House. Interestingly, the bane of his existence was not some cruel slave master, but a fellow slave and family member, his Aunt Katy. The keeper of the kitchen, Katy either took a strong dislike to Fred or decided that he was in need of an extreme run of tough love. She refused to give him enough food—and sometimes any food at all.

She did nothing when other children pushed little Fred aside and stole his portion at mealtimes. Things got so bad that Fred endured desperate moments spent fending off dogs for scraps of leftovers and foraging in creeks for raw shellfish.

One of the trails at Adkins Arboretum, a recommended travel destination near Fred Bailey’s birthplace and old stomping grounds.

Unlike Aunt Katy, the Lloyd family seems to have taken a liking to Fred. Out of the 80 or so enslaved children on the plantation, he was chosen to be the special companion of young Daniel Lloyd. The two became fast friends for a time, exploring every nook and cranny of the farm together.

Some six months into Fred’s time at Wye House, Harriet Bailey came to visit her son. Fred may not have spent much time with his mother up to that point, but he knew enough to trust her with an unvarnished account of his long mistreatment at the hands of Aunt Katy.

I shall never forget the indescribable expression of her countenance. There was pity in her glance at me, and a fiery indignation at Aunt Katy at the same time.

Harriet consoled her son by giving him a piece of ginger cake. Then she turned to Aunt Katy and delivered a blistering rebuke, threatening to tell all to her master and condemning her for the “meanness” and “injustice” she had doled out to the child.

That night I learned the fact that I was not only a child, but somebody’s child. [I felt] prouder, on my mother’s knee, than a king upon his throne.

When he woke up the next morning, his mother was gone. He would never see her again. The adult Frederick Douglass never knew his exact age, or the date of his birthday. After finding his way to freedom, he chose to celebrate the event each year on Valentine’s Day, because he recalled how that piece of ginger cake his mother had given him was cut in the shape of a heart and that while holding him in her arms that night his mother had called him her “Valentine.”

Tubman Travels: 32 Underground Railroad Journeys on DelmarvaA few months after his mother’s memorable visit, another keystone event took place in the life of young Fred Bailey. Word spread through the Bailey clan that two of their members, Jennie and Noah Bailey—they were Fred’s aunt and uncle—had escaped and were trying to make a run for freedom in the North.

Historians who have looked into the case speculate that the couple knew, or at least suspected, that Aaron Anthony was about to put them up for sale. I find it impossible to imagine the turmoil that went into their decision to leave behind two small children, seven-year-old Mary and six-year-old Isaac.

Anthony posted a reward of $150 for Jennie and Noah, but they were never caught. Perhaps in reprisal for the couple’s escape, Anthony soon sold those two young children to a slave trader from Alabama.

In time, word filtered back to the Bailey clan through an early version of the Underground Railroad grapevine that Jennie and Noah had indeed made it to the North and freedom. Looking back on this turn of events in later years, Douglass would see their escape as a first step on his own long journey to freedom. It was the first time he had ever heard that there were places where slaves could become free.

The success of Aunt Jennie and Uncle Noah in getting away from slavery was, I think, the first fact that made me seriously think of escape for myself.… Young as I was, I was already, in spirit and purpose, a fugitive from slavery.

–Written by Jim Duffy for Whimbrel Creations LLC/Secrets of the Eastern Shore. All rights reserved. It’s an excerpt from the book, Tubman Travels: 32 Underground Railroad Journeys on Delmarva.

NOTE #1: The photo up top here is not directly related to the Bailey family or Frederick Douglass. It’s a rare image of an enslaved family that was taken somewhere in Virginia, but it seemed to fit with the story here.

NOTE #2: This is one of four sections in this chapter–it also includes a brief historical overview of slavery on Delmarva; a section in which the adult Frederick Douglass recalls the deeply emotional and musically intricate songs slaves sang while working in the fields; and a guide to sights you can see and travel resources you can access while traveling in the footsteps of Frederick Douglass.

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