Oliver Gilbert escaped slavery at Richland Farm, a Maryland house revered by his descendant

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She’d rehearsed what to say and written a letter explaining herself.

Now, on an afternoon in early May, Stephanie Gilbert pulled up to a liquor store on a busy stretch of highway in Ellicott City, Md. Customers streamed out the door of Pine Orchard Liquors carrying cartons, bottles clinking.

Gilbert, a 55-year-old African American woman with fair skin, green eyes and curly blond hair, had traveled with her fiancé, Steve Brangman, from a Philadelphia suburb, intent on speaking with the store’s owner, Jungsun Kim.

She’d strategized how best to approach Kim, the right words to use.

Gilbert was running through them in her head, standing with Brangman in the parking lot, when she noticed a thin, Asian woman with shoulder-length black hair gesturing to an employee near the back of the building.

“I think that’s her,” whispered Gilbert, a former AT&T executive who now helps run a Black-owned technology firm.

She and Brangman positioned themselves so the owner would need to pass them to enter the store. As Kim approached, Gilbert stepped forward.

“Ms. Kim,” she said, tilting her head and smiling warmly.

Kim stopped and looked at her, uncertain.

“I’m Stephanie Gilbert. I came to meet you. You bought Richland Farm. My family was there. Did you read the history?”

Kim smiled and nodded. “I read the history,” she said, then paused.

“Oliver Gilbert was my great-great-grandfather,” Gilbert interjected. “I wrote a whole letter for you in case you weren’t here.”

“Thank you. Thank you. That was very nice of you,” Kim said.

Gilbert handed her two pages of white paper, folded in thirds.

“Warm greetings on behalf of the family of Oliver Cromwell Gilbert,” Gilbert had begun, trying to channel the ingratiating letters her great-great-grandfather had written to achieve his ends with little power.

“Please accept this introduction and greeting in the spirit in which it is intended: one of the utmost respect and regard for our time on this earth as temporary stewards of our family legacies. …”

In a handful of paragraphs, Gilbert had laid out the three centuries of remarkable history it had taken her a decade to unravel: the five generations of her enslaved ancestors who had labored at Richland Farm and a neighboring plantation in Clarksville for one of Maryland’s most prominent families, Oliver Gilbert’s escape in 1848 via the Underground Railroad, his successes as a free man and his return to Maryland in 1908, when he boldly presented himself to his enslaver’s grandson, Edwin Warfield, the state’s 45th governor. The many years of correspondence between the political scion and the African American lecturer and musician.

In her letter, Gilbert explained that she’d established a relationship with the White descendant who had inherited Richland — the woman who had just sold the estate to Kim for $3 million. During a decade of visits to Richland, she said, “we’ve celebrated Juneteenth, commemorated the ancestors, wept for their trials, and celebrated their triumphs.”

Then, with an audacity her great-great-grandfather might have appreciated, Gilbert made a request: Would Kim allow Gilbert, a complete stranger, to continue to visit the 133-acre estate where her enslaved ancestors are buried? Would Kim agree to take part, she wrote, “in the long and complicated process of healing as African American families search for a … sense of peace with the past”?

Now here was Kim in front of her, smiling agreeably, letter folded in her hand. Gilbert, who knew this might be her only chance to connect with Kim in person, started to make her plea. The path forward depended on whether Kim would listen.

Gilbert was researching her family history in 2010 when she came across a runaway slave ad. The notice had been published in the Baltimore Sun in mid-August 1848, two days after a group of enslaved people had slipped away from a Methodist tent revival.

“$600 reward will be given for the delivery in Baltimore or Howard District Jail, or $200 for either, of the following described Negro Boys, who left the Camp Meeting at Hobbs’ School House.”

The third listed was Oliver, then 16, who was described as “a stout, thick set Black … about 5 feet 7 inches high.”

She stared at the words, imagining her great-great-grandfather’s peril.

“I realized, wow, you ran away and they were really coming for you. There was a reward. There was a bounty on your head,” she said. “You’re 16, and you decide that you’re going to leave your family, leave everything you know behind and go to some unknown place that you don’t even really know if it exists.”

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Oliver, she said, was now alive for her.

A waiter at Richland, he’d been born on the 600-acre estate next door known as Walnut Grove, owned by Col. Gassaway Watkins, a Revolutionary War hero. Oliver, who had nine enslaved siblings, was the son of an enslaved cook at Walnut Grove, Cynthia Snowden, and Joseph Kelly, a free Black man. After Watkins died in 1840, his daughter Margaret inherited Oliver, but, with more servants than she could manage, she gave the boy — then about 8 years old — as a gift to her brother, William Watkins, a physician and the owner of Richland.

There, as he served Watkins in his dining room, the boy bore witness as the plantation’s enslaved people escaped or were sold down South.

First, Oliver’s sister Sarah fled. Then in 1842, his older brother Remus ran away. Later, he listened to the frantic protests of his cousin’s wife as Watkins sold William Dorsey — a trauma that would sear itself into Oliver’s memory.

In 1848, amid rumors that Watkins was considering selling all his enslaved people, a slave trader arrived at Richland and attempted to buy Oliver.

It was clear the time had come to find freedom.

Oliver would later recall listening at the camp revival as the Rev. R.W. Brown, an enslaver himself, warned the human property present to “obey your masters … be faithful, upright and industrious and great will be your reward.”

The teen was disinclined to wait.

As the White worshipers took an evening recess, he and 14 other enslaved people slipped out, with Oliver wielding a revolver “borrowed” from his owner. (“O you my dear reader will call that stealing,” he later wrote in an unpublished memoir.)

The sound of wind rustling tree branches and the rush of the river accompanied the enslaved people as they tried to make haste. “It was very dark and raining and we went feeling our way,” Oliver wrote.

Gilbert had stumbled upon the existence of the memoir from a librarian at the University of New Hampshire who referenced Oliver in her research on the Underground Railroad. Jody Fernald told Gilbert about a Black antiques dealer in Philadelphia who had acquired items belonging to Gilbert’s great-great-grandfather. Gilbert coaxed the woman into selling all but the handwritten narrative.

Finally, Gilbert secured a copy. She read it raptly, thrilled by her great-great-grandfather’s wit and sense of self-worth. Allowing that some might think “it sounds crazy,” Gilbert said she felt her ancestors “calling” her to share her great-great-grandfather’s legacy of resilience, creativity and achievement.

The memorabilia dealer had also mailed Gilbert a large, framed photograph of Oliver as a free man — broad-shouldered and square-jawed with a generous mustache and serious eyes. She propped it up on an easel in front of the desk in her study, a silent sentry urging her on.

By then, Gilbert and Fernald were combining what they knew and expanding their research, leading Gilbert to the archives at the University of Maryland, where she found the correspondence between Oliver and former governor Warfield. Gilbert and Fernald would later publish their discoveries in an academic essay from which some of the history here is taken.

After Oliver and the small band of his enslaved brethren crossed into Pennsylvania the morning after their escape, an abolitionist guided them to the Lancaster home of famed anti-slavery lawyer — and later congressman — Thaddeus Stevens. They were advised to change their names, with Oliver swapping Kelly for Gilbert.

Oliver made use of his skills as a waiter before a relative of his former enslaver spied him working in a New York hotel. He had to flee to Boston, where he befriended famous abolitionists, including William Lloyd Garrison, Harriet Beecher Stowe and Wendell Phillips.

He described working in the offices of Garrison’s newspaper, the Liberator, and meeting William Cooper Nell, a prominent Black activist who at one point edited Frederick Douglass’s newspaper the North Star.

In February 1851, after the passage of the Fugitive Slave Act, Oliver wrote, he watched from a window as Shadrach Minkins, who had escaped slavery in Virginia and was waiting tables in Boston, was arrested by two federal marshals. He recalled running with a crowd to the courthouse to free Minkins, who was whisked away on the Underground Railroad.

For Oliver, the time had come, again, to head further north.

On April 16, 1851, Oliver wrote, he arrived during an early morning snowfall in New Hampshire bearing a note of introduction from Garrison. He stayed in the small town of Lee with the family of abolitionist Moses A. Cartland for two years, working as a cook in their kitchen.

On a trip to Lee during their research together, Fernald introduced Gilbert to Cartland’s great-grandson, Carl Lomison, and his wife, Mary Anne.

Mary Anne went upstairs to the library and retrieved the leather-bound Methodist hymnal that Oliver had left at their home. She placed it on the table for Gilbert to admire and photograph. Gilbert opened the cover to see “Oliver C. Gilbert, Boston” inscribed by her great-great-grandfather and thought “how incredible that I get to sit here and touch something that he touched, that belonged to him.”

Then Mary Anne reached for it. “‘I have to go put it back now,” she said. It belonged with the family’s collection.

Gilbert felt frustrated. The Cartlands, who are now deceased, had a whole library to ensure their ancestors’ legacies; she had comparatively little to show the worth of Oliver’s life. It felt to her that he was still owned by others, what remained of his life theirs to do with as they wished.

In 1884, Gilbert’s great-great-grandfather purchased an expensive suit, donned a hat and a silk umbrella, and returned to Walnut Grove in a horse-drawn carriage driven by a White coachman. He had something to prove.

“When I left there I was very coarsely dressed in rags,” Oliver wrote. “Now that I am a freeman, I want those who are still at the old home, let them see what freedom has done for me.”

He was greeted at the old plantation home by the son of Gassaway Watkins, his first enslaver.

By that time, Oliver was the married father of five children. He and his wife, Maria Thompson, had run a comfortable boardinghouse in Saratoga Springs, N.Y., hosting Douglass and other influential Black lecturers. He took to the lecture circuit himself, yet tellingly, Oliver listed his occupation to census takers as musician.

After settling in Philadelphia, the family formed the Gilbert Jubilee Singers and “became noted near and far for such,” Oliver wrote. They traveled throughout the Northeast, performing at opera houses, masonic temples and other large venues, singing Methodist hymns, opera and plantation songs.

On an early February day in 1908, at the age of about 76, he returned again to Maryland for a visit. Warfield, who had been a baby the year Oliver escaped, had just finished his term as Maryland’s governor.

A Baltimore Sun reporter wrote a story about the encounter, with a racist headline: “Back to Massa Edwin.”

“ ‘It’s been a mighty long time since I runned away from your father,’ said the Negro in a quavering voice. ‘I reckon it was mighty 60 years ago, but I reckon you’ll forgive me this time.” Warfield, according to the Sun, threatened Oliver to “send you around to ‘quarters’ and … cowhide you.’ ”

Oliver, who spoke perfect English, saw the article and took deep offense.

In a letter to Warfield, he wrote, “Old things have passed away and all things have become Negro; though once a slave, to use such language has passed, and we don’t do much reckoning up this way.”

By that point, the two men had been corresponding about their intertwined family histories for at least a decade.

Warfield’s tone was warm but paternalistic.

“I am very proud of the fact that you and your children have been making such an honorable record in life, because it bears out what I have always asserted — that the relationship existing between the master and his servants in the old days was one of affection and loyalty,” the former governor, 16 years younger, wrote Oliver in 1908.

Oliver was ingratiating, careful not to offend; Warfield on occasion sent him money.

“I called because I know you to be friendly to the colored race and in my public speeches, I have had occasion to say a good word for you and your family,” Oliver wrote him.

Finally, in 1911, Oliver decided to answer Warfield’s request for memories of his “boyhood days.”

“There are some very pleasant memories of the house, and some that are not so pleasant to recall,” Gilbert wrote. “You said, when I met you in Baltimore, ‘That I did not run away because I was treated so badly, but that I had a burning thirst for liberty, and could not resist the temptation.’ That was just it, a love of liberty, a desire to be free is an element inherent in man’s nature. When I saw your Uncle William Watkins sell poor cousin William Dorsey to the slave trader … his wife begging so hard, in vain … it set me to thinking.”

The following year, Oliver died.

A century later, on a sunny May day in 2011, Stephanie Gilbert and her cousin arrived on the broad, covered porch of Richland.

They’d been invited to lunch after Gilbert tripped upon yet another Sun article. The story detailed the lavish efforts by Melanie Dorsey and her husband, Dan Standish, to restore the 300-year-old property to its former glory.

Gilbert had called Dorsey and explained her family connection to Richland.

Now the couple, both attorneys, greeted their guests and ushered them inside. Dorsey was nervous, she remembered in an interview, wanting to say the right thing.

When she inherited the estate in 2005 from her great-aunt and great-uncle, Dorsey had been left a key to the attic. It was full of the home’s original 18th- and 19th-century furnishings, hair still in the brushes.

Gilbert could picture Oliver whisking past the grand staircase, taking dishes out of the built-in china cabinets, setting tea and coffee down on the pie crust tables, moving between the kitchen and the dining room. She felt as though she could reach out and touch him.

“You’re here,” she imagined him saying. “You’ve made it all the way back.”

The foursome sat down for lunch at a long wooden table in the original log kitchen. She marveled that she, Oliver’s great-great-granddaughter, was now being served by a descendant of his enslaver. Then Dorsey, a soft-spoken woman with wispy blond hair, apologized to Gilbert for the harm that her ancestors had caused Gilbert’s ancestors.

“I know that there would have been enslaved people in the family, but I never really considered it,” she said. “I should have.”

Gilbert felt profoundly moved. She knew by then, through DNA testing, that her family was also directly descended from the Watkins family.

“I think we should both be glad that we didn’t live 150 years ago,” Gilbert said.

Standish had poured himself into restoring the house as close to its beginnings as possible, hiring Amish workers from Pennsylvania to restore the horsehair plaster in the spacious home and a contractor to replace damaged siding with North Carolina pine cut with the same unusual saw as the original. Over time, he collected enough documentation to put Richland on the National Register of Historic Places.

Dorsey had grown up hearing her father, Benjamin Dorsey — a prominent D.C. attorney — talk about losing baseballs out in the Richland countryside as a child. Yet she had never been to visit the property herself until she learned that it had been bequeathed to her, somewhat inexplicably, by her father’s sister, Achsah Bowie Dorsey Smith, a society editor for the Washington Times-Herald.

She was largely incurious about her family’s history, she said, even more so after she learned from Gilbert about her ancestors’ lives as enslavers. And yet Dorsey, too, felt something when she spent time at Richland — a strange sense of safety, she said.

Years passed, with Gilbert visiting to commune with her ancestors on the land. Then in 2020, the couple asked Gilbert and Brangman to join them for a Juneteenth picnic on the side porch. Gilbert and Standish swapped fresh history findings, while Dorsey took in the pastoral vista, as rain began to pour from the sky.

The next morning, Gilbert received an email from Dorsey. She and Standish had not wanted to ruin the picnic with the news, she said, but they had decided to divorce. Even so, she assured Gilbert that as long as she was alive, she would be Richland’s owner, and Gilbert would always be welcome to visit.

Yet in the end, Dorsey said, she did not feel she could keep the house. Now retired with a progressive disability that has required surgeries and sapped her energy and mobility, how could she possibly continue to maintain such a large estate?

First, Dorsey offered to sell the house to Standish, but he declined. Then she put Richland on the market.

“I was in shock,” Gilbert said.

In May of last year, Gilbert and Brangman volunteered to drive south, pick up Dorsey, who was too disabled to drive, at her home in Chevy Chase, Md., and take her to Richland in advance of selling the home.

Gilbert asked Dorsey whether she would give her something that her enslaved ancestors may have held or gazed upon. Dorsey asked her what she wanted. Gilbert chose a rusted brown kettle on the kitchen floor, thinking that it was perhaps from Oliver’s era. She would eventually discover that it was from a later period.

Gilbert said she also asked Dorsey whether she could spend just one night in the house by herself before it was sold, to feel her ancestors alone, to say goodbye. But Dorsey doesn’t recall the request.

Gilbert left the house at the end of the visit fuming inside. Her ancestors’ labor — not just on the plantation but as workers the family hired out, keeping their wages, Gilbert said — had allowed Dorsey’s forebears to build their wealth and status. Now Richland would be “sold to the highest bidder,” Gilbert said, and she was powerless to do anything about it.

Oliver’s history is also hers, she said, and yet “I’m not allowed to have any tangible part, because quite frankly, the White folks who were involved are just hoarding everything.”

In March of this year, after reaching a deal with Kim that required her to empty the house before the closing, Dorsey auctioned the home’s furnishings. Although Gilbert had asked Dorsey in a Feb. 13 email to let her know if she planned to auction Richland’s contents so she could purchase items, Dorsey let her know on March 21, the evening before the week-long bidding period ended. Dorsey said in an interview that she had to act more quickly than anticipated, but Gilbert said she felt unheard.

“The auction of our fragile history is underway and ends tomorrow?!” she wrote Dorsey in an email, “Well, we have ended an era. Several eras.” Still yearning for something tangible, she spent more than $5,000 bidding on Richland’s remains, including an Edwardian Mahogany dressing mirror, a late-18th-century Chippendale pie crust table, and an embroidery sampler stitched by Dr. Watkins’s daughter, who was Dorsey’s great-great-grandmother.

The day after, on March 23, Gilbert wrote Dorsey a blistering email.

“When I think about Richland and its contents, I am not interested in such for the monetary value or desirability of a piece. Truly what matters most is what those items have ‘witnessed’ of my family’s past.

“… You are the descendant of a shameful legacy and had/have been granted a powerful opportunity to course-correct, yet you have squandered that in a continuum of self-serving actions driven by a lack of reflection, sensitivity and awareness.”

Dorsey was stunned. “I offer my deepest apologies, knowing that likely means nothing to you,” she emailed back. “I do not know how to undo the hurt, pain I have caused you and your family.” She’d freely given Gilbert the kettle that she wanted, she said. Now she offered to mail her three more items from the kitchen hearth. They have not arrived, Gilbert said.

In a May interview, Dorsey said she has been sensitive to racism since she was a child, asking her mother to stop the car so they could be witnesses for a Black man who had been rear-ended, so certain was she that he would be ill-treated because of his race. She had seen firsthand how race plays out in society.

Dorsey said she believes in reparations for the descendants of enslaved Americans under consideration by elected officials across the country and has been following closely as Harvard University, her law school alma mater, debates what to do about its ties to slavery. But what, if anything, did she owe Gilbert for her family’s sins of slavery and the wealth they built on the backs of Gilbert’s ancestors? It was a new thought.

“I felt I owed her decency as I would any human being,” she said softly. “I accorded her a lot of respect because of her tenacity, my goodness, and her strong ties to her roots. She was insatiable in wanting to know all of that.

“I never thought of it as owing, as owing access or something like that. I just thought of it as something you do.”

Outside Pine Orchard Liquors, Gilbert made her appeal to the new owner of Richland. She did not know how much Kim, a South Korean immigrant, knew about the history of American slavery. Yet here was her one shot.

She explained to Kim the connection she had forged with Dorsey and Standish. “My family is buried on the site,” Gilbert said. “They’re buried in the back behind Richland,” which, according to Oliver’s memoir and other documents, had served as the main slave quarters for both plantations. Following common practice, the graves of the enslaved would have been unmarked.

Kim said that she was not yet living there. She hoped to build a greenhouse and a distillery on the property. “These are things I’ve been dreaming of,” Kim said over the roar of traffic. “I don’t know if it will happen, but at least I am going to try.”

Kim mentioned that the house was still unfurnished.

“Would you let me spend the night there?” Gilbert asked.

“Of course,” Kim said.

“And you don’t have to have furniture in there for me to spend the night,” Gilbert said. “I would spend the night when it’s empty. I like to connect with my ancestors. Do you understand that?”

“I’m sorry,” Kim said, her eyes darting to the store.

“You have to go in now?”

“Yes. I’m sorry. Give me your phone number. … Yes, you can stay. Give me a call.”

Gilbert offered her phone, and Kim created a contact for herself.

“Thank you,” Gilbert said as Kim headed past her.

Over the next two weeks, Gilbert said she called and texted Kim. She came down twice from Philadelphia and dropped into the store, hoping to find Kim there again. The second time, Kim’s son, who was at the register, promised to give the message to his mother.

On a Saturday morning in late May, Gilbert said she received a call from Kim’s 24-year-old daughter. She said her mother had asked her to call. Their family is very private, she explained. They had bought Richland because it was secluded. They didn’t want other people around them.

A week later, Gilbert received a text from Kim asking her to call. Kim apologized for not reaching out directly earlier, but repeated what her daughter had said.

In an interview with The Post, Kim said Gilbert’s visit caught her by surprise. She had purchased Richland as a retreat for herself and her children. She said she has had a difficult life and finds it wearing to be around people. “I am not a social person, whatsoever,” she said.

After consulting with her daughter and son and a couple of her children’s Black friends about Gilbert’s request, she said she does not feel obligated to grant access. She knows the history of Richland and slavery in the United States, but that was “over a hundred years ago.” There are historic sites all over the country where Gilbert can go to engage with the enslavement of African Americans, she said.

Unlike Melanie Dorsey, she said, her family’s history is not entwined with Gilbert’s: “This is independent, private property. It’s not open to the public. … My children, everyone says ‘no.’”

She also shared Gilbert’s letter with a Howard County planning official who, while curious about the possibility, said the county has no record of enslaved burials at Richland. This was enough for Kim. “I did my duty and try not to harm anybody,” she said.

The rejection of her request hit Gilbert like “a door slam.” That familiar sense of frustration and powerlessness welled within her.

“I feel like this is the end,” she said quietly. “It’s the end of Richland. It’s the end of the connection.” And then she thought about her great-great-grandfather.

Oliver’s courage, the road he had paved for her, Gilbert decided, wouldn’t allow her to walk away from his story. He “gave me the power and the privilege,” she said, “to go back and say, ‘Knock, knock, knock. We need to have a conversation.’

We are not going away — right? Ever. Here we are. Generation after generation after generation, you will answer to us.”

Story editing by Lynda Robinson. Photo editing by Mark Miller. Copy editing by Mina Haq and Wayne Lockwood. Project editing by Jay Wang. Design by Kathleen Rudell-Brooks.