Illinois’ Underground Railroad: The Stories Of Descendants

There is a beautiful duality to the first Chicago site recognized as part of the Underground Railroad.

In front, a historical plaque unveiled in 2019 solemnly marks the former Jan and Aagje Ton Farm, 557 E. 134th Place, as part of the National Park Service Network to Freedom program.

Chicago’s Finest Marina exists in the back, the sole Black-owned marina in the city. Ronald Gaines Sr. bought the farm in 2005 after enjoying the marina as a boater in the 1980s, and now plans to offer event space to those wanting to make memories in a historic place.

“It’s a little getaway for ourselves, but because of the rich history, we felt obligated to open it up more, so other people can enjoy and see it,” said Gaines, 71, a retired Chicago police sergeant. “Because it’s not only my history — it’s everybody’s history.”

Over the past eight months, the Chicago Tribune has embarked on an in-depth examination of the journeys through Illinois of enslaved people who sought better lives for themselves. We have visited the state’s Underground Railroad sites that aided in their escape, spoken to descendants of those freedom seekers, and delved into our archives. The resulting series depicts what life was like during a time when thousands of people made this pilgrimage in the hopes of finding freedom — and how their history ripples into the present day.

This week, we’re sharing what we learned through profiles, an interactive map detailing the Illinois Underground Railroad, and interviews with the historians who helped tell these stories.

We start with six descendants of freedom seekers with ties to Illinois. Their stories chronicle their knowledge and pride of being connected to American history.

Gaines of the trade

Underground Railroad Ronald Gaines Jr., left, and his dad, Ronald Gaines Sr., stand at the Chicago’s Finest Marina, owned by the elder Gaines, on Aug. 2, 2023, in Chicago. The family’s genealogical hunt uncovered they are descendants of a freedom seeker who settled in Michigan. (Terrence Antonio James/Chicago Tribune)

In some ways, Ronald Gaines Sr.’s property reflects the multitudes of the man himself: fun-loving and spirited, but with a deeply rooted interest in the colorful and, at times, painful past of the Gaineses who came before him.

“To have a connection with some of these people, you start to wonder how much of him is in me?” Gaines said. “You never know what you will find; it’s a treasure hunt.”

That genealogical hunt first led Gaines and his son, Ronald Gaines Jr., to Marquette, Michigan, where their ancestor William Washington Gaines sought freedom after fleeing Virginia. Washington Gaines was the biological son of Virginian enslaver Pitt Gaines and an enslaved woman he owned, Nancy Wheatley.

Underground Railroad William Washington Gaines sought freedom in Michigan after fleeing Virginia. Gaines was the biological son of Virginian enslaver Pitt Gaines and an enslaved woman he owned, Nancy Wheatley. (Marquette Regional History Center)

Pitt Gaines freed his son when he reached adulthood, and Washington Gaines then bought the freedom of his wife, Mary. After Washington Gaines was injured working in the copper mines of Michigan’s Keweenaw Peninsula, the couple settled in Marquette.

With the less restrictive society of the Lake Superior frontier and without the risk of slave catchers traveling as far north as the Upper Peninsula, the two lived for decades in an area known to this day as Gaines Rock. Their story eventually became part of Betty DeRamus’ book, “Forbidden Fruit: Love Stories from the Underground Railroad,” which is where the younger Ronald Gaines came across it.

Further research over some two decades led Gaines Jr. to a cousin in Central America, whose family tree yielded another fascinating connection. The Gaineses, he found, are distantly related to Josiah Henson, whose autobiography inspired the groundbreaking anti-slavery novel “Uncle Tom’s Cabin.”

The revelation — and the newly discovered relatives it yielded — shows how powerful it can be to look into histories that can be fraught with tragedy, Gaines Sr. said.

“I think we have been put off from trying to discover who we are,” he said. “We can’t be fearful where the path takes us. … You’ve got to take the good, the bad and the bittersweet.”

Lt. Gov. Juliana Stratton, left, and U.S. Rep. Robin Kelly, center right, unveil an Illinois State Historical Society marker at the site of the former Jan and Aagje Ton Farm in Chicago on Sept. 24, 2022. The farm, which is now Chicago’s Finest Marina, was used as a stop on the Underground Railroad. (John J. Kim / Chicago Tribune)

Washington Gaines’ birth, for example, was the result of the ugly practice of slave owners impregnating women who were not free to refuse them. But from that came a happy life he built for himself, and the generations that followed.

Gaines Sr. has built quite a legacy himself, with six children, 14 grandkids and one great-grandchild. All but one — a Seattle resident — live in Illinois.

He’s also excited to share the Chicago’s Finest Marina space with tour groups and community members. He envisions a business plan that melds the history of the land with momentous life events, such as weddings and family reunions. Gaines Sr. is currently seeking funding to expand programming and offer boat rentals for those who want to explore the African American Heritage Water Trail.

Your genealogy “makes you want to grasp” the details and try “finding out what they actually did in their lives,” Gaines Sr. said.

His son agreed.

“We all came from somebody, somewhere,” he said. “The truth is out there. You just got to look for it, turn over the stones.”

The memory keeper’s daughter

Underground Railroad Leanna McGee stands at The Mother Rudd Barn, a site believed to be connected to the Underground Railroad, in Gurnee on Aug. 21, 2023. McGee is a descendant of William Donnegan, who was a shoemaker who aided freedom seekers crossing through Illinois. (Terrence Antonio James/Chicago Tribune)

Leanna McGee is one of Connie McGee’s four children and the namesake of her great-great-great-grandmother, Leanna Donnegan Knox. And like her mother, Leanna McGee, 39, has taken up the mantle as holder of the family tree.

Unlike her mother, Leanna McGee has the modern convenience of online databases — and a history degree — to aid in her quest to fill out every ancestral branch.

“Once you start, it’s addicting,” said the Waukegan School District 60 teacher, who lives in Gurnee. She juxtaposed her genealogy research with her knowledge of American history, she said, “to fill in blanks and get a picture of what life was like for my ancestors. And the more I dug into it, the more interested I became.”

She has always been a history buff. In high school, the Springfield native volunteered as a guide for historical reenactments at the Old State Capitol. Nowadays, she and her mother go on research trips to Kentucky — where Donnegan Knox was born free in Hopkinsville in 1794 — to pore over court records, where Donnegans pop up in a variety of spellings.

The most well-known among them is William Donnegan, the youngest of Donnegan Knox’s children. He was a shoemaker by trade — and was said to have made shoes for Abraham Lincoln — and owned his own business and property. He also aided freedom seekers crossing through Illinois.

William Donnegan The Chicago Tribune published a story on Aug. 17, 1908, describing the Springfield race riot, including a youth who confessed to helping lynch William Donnegan. (Chicago Tribune)

He was murdered at 80 years old during the 1908 Springfield Race Riot, where a racist mob beat the elderly Donnegan senseless and slit his throat before lynching him in a schoolyard.

Donnegan is buried in Oak Ridge Cemetery, which is also Lincoln’s final resting place. Unlike the former president’s, his grave is not marked. It rests in a portion of the cemetery designated as the “Colored Section.”

“The name became infamous because of the tragedy around William Donnegan, but there were so many other Donnegans that were foundational in building the Black community in Springfield early on,” McGee said. Two of William’s siblings helped create the St. Paul African Methodist Episcopal Church in 1843, and another worked to establish Black education in Illinois.

The family came to Springfield from Hopkinsville, where Donnegan Knox had owned property, birthed 10 children and married a man after she bought his freedom from his enslaver. She was the biracial child of a Black father and a white woman, whom Leanna McGee said she believes was an Irish woman in indentured servitude.

The first Leanna’s mother was never listed by name, but court documents showed Leanna Donnegan Knox was free because of her birth mother’s race, her namesake said.

“Which is ironic, because if it was flipped the other way, and her father had been a white man (instead), she would have been enslaved,” Leanna McGee said.

Leanna McGee Leanna McGee looks over genealogical information collected about her family at her home in Gurnee on July 3, 2023. McGee is a descendant of William Donnegan, who aided freedom seekers crossing through Illinois. He was murdered at age 80 during the 1908 Springfield Race Riot. (Terrence Antonio James/Chicago Tribune)

Being free and Black in a slave state was likely what spurred the Donnegans to move to Springfield by 1847, their descendants say. At the time, the Fugitive Slave Act of 1793 made it legal for enslavers to hunt down freedom seekers in free states and bring them back to bondage — putting formerly enslaved people at risk of recapture for the rest of their lives, and threatening free Black people with slave catchers willing to profit off anyone they could entrap, free or not.

Donnegan Knox had 21 white men sign a court statement verifying she was free, an extensive process required to travel safely at the time, Leanna McGee said. Those papers still exist, 176 years later.

“It’s real special that we have those documents to help get an image of how they lived,” Leanna McGee said. “I’m sure that was a constant fear in their mind, that they could be sold into slavery, even though they were born free.”

Currently, Leanna McGee is focused on trying to connect their lineage to Ireland. They know they’re Irish, but there are missing roots without the name of Donnegan Knox’s mother. It’s part of the “uphill battle” African Americans experience in tracing their history through the poorly kept records of people who were treated as property, Leanna McGee said.

“But I encourage everybody to try,” she added. “When I have hardships, I can think back to those people and the hardships they went through, and I can make it because they made it. They are who you are. They’re living inside of you. I don’t think that you can forget about them.”

Keeping up with the Joneses

Underground Railroad Bruce Purnell is a descendent of John Jones, who was born free in 1816 in North Carolina and eventually moved to Chicago. Jones aided freedom seekers as they traveled on the Underground Railroad. (Terrence Antonio James/Chicago Tribune)

Twenty years ago, Bruce Purnell’s father handed him a duffel bag filled with a treasure trove of ancestral records and documents.

“When my father saw that I was the one that cared about this stuff, he gave me the bag,” said Purnell, a psychologist based in Washington, D.C.

What he found inside was “an unbelievable love story.”

John Jones was born free in 1816 in North Carolina, and became a tailor’s apprentice in Memphis, Tennessee, which is where he met Mary Richardson.

Fearing a tailor’s relatives would try to claim him as a slave, Jones traveled back home to get proof of his free status.

After he returned, Richardson’s family moved to Alton, a southern Illinois river town that became a beacon for abolitionists and an Underground Railroad destination for Missouri freedom seekers.

Jones followed. The couple married, and eventually moved to Chicago.

In Chicago, Jones made a name for himself as a mainstay at gatherings known as Colored Conventions, where he fought for the repeal of the restricting Illinois Black Codes. Chicago artist Richard Hunt memorialized the man and his work with the 1968 sculpture John Jones, which sits in the DuSable Museum of African American History.

Portrait of John Jones John Jones was born free in 1816 in North Carolina and eventually moved to Chicago. Jones aided freedom seekers as they traveled on the Underground Railroad. (Joseph Aaron Campbell/Chicago History Museum)

For two decades, he toiled while aiding freedom seekers, running a tailoring business, fighting for the Black vote, serving as a Cook County commissioner, and helping to found Olivet Baptist Church. Mary Richardson Jones’ philanthropy, suffrage work, and assistance to freedom seekers led the likes of Frederick Douglass, Ida B. Wells, Susan B. Anthony and Mary Ann Shadd Cary (the first Black female newspaper publisher) to cross the Joneses’ path.

“In this duffel bag, I had the pictures of John Jones and Mary, letters from Frederick Douglass and how he felt about John Brown’s raid,” Purnell said. “Looking at this is like knowing you’re now responsible for the legacy.”

Like his ancestors, Purnell continues to fight for liberation — but in a different way.

Purnell is the founder of the Love More Movement, a nonprofit that offers training for life coaches and community leaders focused on mental health and healing for those with trauma. Rather than the Underground Railroad, he thinks of it as an “overground freeway” to free people entrenched in intergenerational cycles of trauma that contribute to chronic health conditions and long-term mental distress.

“We don’t understand (the full impact of) what happened to us — 400 years of being sold, raped, beaten, lynched, and having to keep all of that in,” Purnell said. “Just labeling it doesn’t get us to a place of being able to release it and move to joy and know that we’re valuable enough to love and be loved. We’re valuable enough to heal and transform.”

Brotherly love

Underground Railroad Gerald McWorter, a descendant of “Free” Frank McWorter, stands outside his home in Urbana on Aug. 18, 2023. Free Frank founded New Philadelphia, an integrated town in western Illinois, the first in the nation to be registered by a Black man. (Terrence Antonio James/Chicago Tribune)

For nearly 50 years, New Philadelphia was an integrated town in western Illinois, the first in the nation to be registered by a Black man, known as “Free” Frank McWorter.

Just over 182 years after McWorter founded the town named for brotherly love, his great-great-grandson, Gerald McWorter, co-authored a book with his wife, Kate Williams, narrating its history.

“Once you connect the dots, you look for more dots, and more dots may change the story,” Gerald McWorter said. “That’s how history continues to be rewritten.”

A bust of “Free” Frank McWorter was made by Shirley McWorter-Moss. McWorter was the first Black person to legally found a community in America in the 1830s. (Armando L. Sanchez / Chicago Tribune)

After getting his start as a gunpowder manufacturer in Kentucky, Frank McWorter bought his wife’s freedom first, then his own before moving to Illinois. He bought and sold 144 lots of land in New Philadelphia, using profits to free 16 family members across three generations from enslavement. Frank McWorter helped others escape enslavement as well, and New Philadelphia became a destination for newly free Black Missourians.

The integrated town grew to 160 people by 1865, but was ultimately abandoned after Frank McWorter’s death and the decision to build a planned railroad elsewhere, instead of near New Philadelphia.

Flashback: Tucked away in rural Illinois is the site of America’s first town founded by a free Black man. ]

By the 21st century, there was barely a trace of New Philadelphia, but archaeologists began excavating in 2003 in hopes of preserving the buried historical site. As the Black Lives Matter movement increased in prominence, interest in the site grew, Williams said.

“They want to learn Black history because white people are realizing that Black history is American history,” Williams said. “And Black people want to know their history more and more. It’s a standing-up moment.”

The New Philadelphia National Historic Site became a national park at the end of 2022.

A painting of New Philadelphia by Thelma McWorter Kirkpatrick Wheaton shows the first community legally founded by a Black person. The integrated town in rural Illinois grew to 160 people by 1865, but was ultimately abandoned. (Armando L. Sanchez / Chicago Tribune)

McWorter has always known his history. He recalls how his two aunts — one an activist and teacher of trade union rights, and the other a member of the U.S. Communist Party — were significant in his life. While their views differed, they shared a common interest in Black leadership and were friends with W.E.B. Du Bois, a civil rights activist and co-founder of the NAACP, and his Freedom newspaper co-founder Paul Robeson, an actor and singer who became a political activist.

“I had that as a legacy that I was socialized into,” he said.

As for getting the next generation excited about discovering their roots? In a time when politicians are structuring school curriculum to omit Black American history, knowing one’s own background is vital, McWorter said.

“The stark reality of political culture is out in front of everybody — the book banning and trying to whitewash curricular materials — this is the time for an assertion of positive stories,” McWorter said.

Writing on the wall

Underground Railroad Juliet Lavon Woodson-Wilson stands in Springfield’s Oak Ridge Cemetery, where several of her ancestors are buried. Woodson-Wilson can trace her family back to those seeking freedom through the Underground Railroad. (Terrence Antonio James/Chicago Tribune)

While Juliet Lavon Woodson-Wilson might have officially been a music teacher, she taught history just as readily.

“I would share with the students the history of the Negro spiritual or the rhythm and blues, wanting them to be proud of their heritage,” said the 91-year-old Springfield native. “To this day, I’m very strong on that. I think it’s important that you know from whence you came and how you got there.”

Her armload of white binders detail a family tree that stretches back 145 years in the state capital, and she can chart seven generations of Woodsons even further, to 1840. She rattles off the names and the marriages as easily and as fast as her own.

She remembers her great-grandfather was enslaved for a few years of his early life. She recalled how he taught her how to play checkers and learn life skills in the process. She recollects her maternal grandfather, Eugene Jones Jr., was a bell hop and server in the late 1920s and early 1930s who worked in places that would have refused to serve him.

“I remembered asking him one day why he had a rock in his walk,” she said. “We didn’t have elevators all the time in hotels, so he learned how to carry luggage and walk steps regardless of how many floors it was.”

There is pain in that history, even after generations of Woodsons lived in the free state of Illinois. Over the decades, the Woodson line endured two murders: LeRoy Woodson was shot and killed walking home from work, and a mob of white men killed Eugene Jones Sr. in 1894.

Underground Railroad Juliet Lavon Woodson-Wilson, who can trace her family back to freedom seekers, looks through documents at the Springfield and Central Illinois African American History Museum in Springfield on July 18, 2023. (Terrence Antonio James/Chicago Tribune)

Jones’ funeral took place at the Donnegans’ St. Paul AME Church, connecting her past to that of another descendant mentioned earlier.

“When I get into discussions on race relations, I tell them that I don’t have to move South to know about relationships with people who don’t care for my hue,” Woodson-Wilson said.

Her passion for genealogy was sparked 40 years ago, when she saw similar enthusiasm in her close friend Charlotte Johnson, a veteran historian of Black history in the Underground Railroad port of Alton, Illinois.

“I got hooked,” Woodson-Wilson said, “and I haven’t stopped since.”

Woodson-Wilson wrote the family plaque that hangs in the Springfield and Central Illinois African American History Museum, putting her lineage literally on the wall.

“I have seen improvements in the city,” she said. But “we still have a long way to go. It’s been a privilege for me to see some parts of that history unfold within my household.”

Her younger brother Allan Woodson, 78, was a Springfield alderman in the 1980s, a time when it took a historic lawsuit to give Black people a seat at the table.

“We have people in our city that have given all they got so that people can have a better way of life,” Woodson-Wilson said.

And that’s been true of America and its relationship with its Black citizens all along, she added. “We shaped each other, because that was the only way we could survive,” she said.

Now, Woodson-Wilson is hoping to have the time and luck to find which ship first brought the Woodson family to America.

She also recently gathered with her family to talk about her will, going over which possessions loved ones would want to inherit. Multiple grandchildren expressed a desire for her genealogy set — those stacks of white binders and piles of black-and-white photos she has assembled over four decades.

Woodson-Wilson was surprised, but happy to hear their interest, she said. To her, it means the next generation has learned the history lessons she has always hoped to impart.

Teen spirit

Underground Railroad Kimberly Simmons, an ancestor of Caroline Quarlls, sits at Alice’s Garden Urban Farm in Milwaukee on Aug. 21, 2023. Quarlls was the first enslaved person to travel through Wisconsin using the Underground Railroad and spent time on the land that includes Alice’s Garden. (Terrence Antonio James/Chicago Tribune)

On an ordinary day in 2003, Kimberly Simmons came across an article by Illinois historian Larry McClellan detailing a connection between Chicago’s south suburbs and the 1843 journey of Caroline Quarlls, a 16-year-old who fled to freedom from St. Louis to Sandwich, a Canadian settlement on the Detroit River near Windsor, Ontario.

Simmons, a Detroit resident, pulled up a portrait of the teenage freedom seeker and felt an instant connection.

“That day I looked at her, I could see my grandmother, my mother, little me,” Simmons said. “I started calling around to relatives and no one knew anything, and then I found pictures tied to her in Milwaukee.”

She felt called to share Quarlls’ story and those of other ancestors: stories of truth, perseverance and resistance evident in too-often untold Black history. She began serving as a network partner with the National Park Service’s Network to Freedom, telling the story of the teenage Quarlls, who was able to pass as a white woman as she journeyed with abolitionist Lyman Goodnow through Alton, Illinois, and through Wisconsin, Indiana and Michigan.

Underground Railroad Caroline Quarlls Watkins, shown here when she lived in Sandwich, Ontario, was the first enslaved person to travel through Wisconsin using the Underground Railroad. (Wisconsin Historical Society)

Quarlls dodged pro-slavery lawyers and slave catchers driven by a $300 reward (the equivalent of about $12,400 in 2023) for her recapture, and was the first enslaved person to travel through Wisconsin on her way to freedom. Once in Canada, she married another emancipated freedom seeker named Allen Watkins and went on to raise six children.

Simmons, Quarlls’ third-great-granddaughter, penned a book about Quarlls with McClellan in 2019, “To the River,” in which she connects Quarlls’ lineage to Dabney Carr, a friend of Thomas Jefferson; Meriwether Lewis of Lewis and Clark fame; poet-playwright Langston Hughes; and Lewis Sheridan Leary, who died in the 1859 raid at Harpers Ferry. Simmons can count two signers of the Declaration of Independence among her ancestors.

“I have engaged in this history because it has driven me to find out about other people and places and what makes the places and people tick,” Simmons said. “What happened during this story that is so tied to who I am?”

She is adamant that other descendants need to look for the truth in stories and put in the time to learn how to separate myths of the Underground Railroad from the reality.

“I tell my story because there are a lot of people out here that can’t,” Simmons said. “Our people have been survivors. We are all heroes — we persevered.”

But in looking back, she said, it’s just as important to look forward.

“A lot of times people start talking about the past, but let’s start talking about how that past put us where we are today,” she said, “because our stories aren’t over yet.”

Photographs with this story were made using an iPhone Tin Type filter.

Read more

Visit and watch for the Tribune’s special section on Illinois’ Underground Railroad, in print Sept. 17.

This series is presented by the Abraham Lincoln Presidential Library and Museum.

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