Juneteenth is meant to honor the end of slavery, but it’s also the perfect time to reflect on how far the nation has come and how far we as a society must go to truly reckon with our past. To strengthen my relationship with the holiday as we approach its 159th commemoration, I decided to replicate the journeys of my ancestors seeking freedom. Using the National Park Service’s “Network to Freedom” map, I learned about Underground Railroad stops in the Chicago area, the ideal starting point for my trip, as it’s close to home.
I chose to model my expedition after that of Joshua Glover, the formerly enslaved man who found freedom after abolitionists in Wisconsin, led by Sherman Booth, helped rescue him from his captors. Their actions and the community of abolitionists who refused to comply with the Fugitive Slave Act of 1850 set the stage for Wisconsin to become the first state to nullify the law, a key moment in the events leading up to emancipation.
Before delving too deeply into the journey, I think it’s important to address my own biases and place within the larger community of historians. I’m a middle-aged, able-bodied, Black male with the time, resources, and health to participate in a long-distance excursion. My journey wouldn’t be possible without the hundreds of people who have celebrated and studied the stories of the Underground Railroad. Unlike those who made this journey in the past, my load is lightened by the certainty that I never feared violence, assault, or capture.
Join me as I traverse 100 miles from Chicago’s South Side to Milwaukee to retrace the steps of people who sought freedom and a better life. I hope that those reading this can better understand the absurdity of a system where freedom is determined by geographic location and recognize the need to protect the people, communities, and lands that connect us.
The Southside: Chicago and Quinn Chapel African Methodist Episcopal Church
I wanted to start where Black excellence has been celebrated for more than a century. Chicago is my home, and it was founded byJean Baptitist Point du Sable, a Black man who married into a Potawatomi family. Quinn Chapel AME is the home of Chicago’s first African-American congregation, an Underground Railroad site where a group of four Black women helped guide freedom-seekers along the Underground Railroad. The original church was destroyed in the Great Chicago Fire of 1891 and rebuilt in its current location. Quinn Chapel AME, located in the historically black neighborhood of Bronzeville, would have been imposing to slave catchers from the south and inviting to those seeking refuge on their journey north. It has served as a convening place for nearly 200 years. Speakers, including Frederick Douglass, W.E.B. DuBois, Dr. Martin Luther King Jr., Susan B. Anthony, and President Barack Obama, have all delivered sermons from the pulpit since the church opened in 1847.
The North Shore: Abolitionist Heritage & Decent into Segregation
I always felt safer on the South Side of Chicago rather than in the neighborhoods along the North Shore. A legacy of redlining, which kept Black people out of affluent enclaves along the North Shore, and a busy schedule playing football meant I never really had a desire to venture to this part of the city. I expected to find the home where Kevin was left Home Alone to thwart Marv and Harry. However, in Winnetka, I learned about people who fought for abolition in suburbs like Lake Forest, Highland Park, and Waukegan. As a product of Naperville, an affluent southwest suburb, I never considered that Black people might have thrived in these white spaces. What if I had been exposed to Evanston, Illinois, the home of Northwestern University, and the descendants of slaves who successfully fought for reparations? Perhaps I would have learned at an earlier age about the community of formerly enslaved people who congregated at places like the First Baptist Church of Lake Forest before the Civil War. Maybe abolitionists like Sylvester Lind, a Scottish immigrant who utilized his wealth to found Lake Forest College, would have been as familiar to me as Frederick Douglass. Lind would go on to sell land to the residents who developed Lake Forest’s first Black community.
Commemorating history and enjoying the sunset while walking a portion of the Underground Railroad. | Photo by Sherman Neal II
Kenosha: Abolitionist Wisconsinites Historic Fight Embrace Freedom Over Hate
I vividly remember the events of 2020, when Kyle Rittenhouse, a white man, murdered two men. Before that day, a Kenosha Police Officer shot and paralyzed Jacob Blake, inspiring Rittenhouse to travel to Wisconsin with the intent to kill. Today, Blake is paralyzed, and Rittenhouse is a right-wing darling (a current Georgia Congresswoman nominated Rittenhouse for a Congressional Gold Medal). Eventually, I shifted away from the events of 2020 and towards the region’s rich heritage of abolition. After stopping for breakfast inside a traincar at the historic Frank’s Diner, I made the short trip towards the site of Reuben Deming’s home, a final destination for many fugitives before boarding ships in Kenosha harbor bound for Canada.
Pausing to watch children play on the library square, I saw Kenosha as a place that embraced freedom. In his speech “I’ve been to the mountaintop,” Dr. Martin Luther King Jr. spoke about seeing the promised land in Memphis the day before he was assassinated. Reflecting on Kenosha, I found his admonishment in that speech rings true today. “I may not get there with you. But I want you to know tonight that we, as a people, will get to the promised land,” Dr. King said. If he could travel to Memphis to stand in solidarity with sanitation workers and expand his liberation message to encompass the labor struggle, then I could certainly find a way to see opportunity in a place that once seemed to embrace white supremacy.
Racine to Milwaukee: A raid on the Shores of Lake Michigan and the road to emancipation
Due to the interpretation and preservation work by local leaders and the National Park Service, I was familiar with the history of this leg of the journey. At the First Presbyterian Church in Racine, I paused to imagine 500 men gathered and determined to travel 25 miles north to Milwaukee to rescue Glover from bondage. En route to Milwaukee, I envisioned these men and the support they would have had to sustain their effort. The bookstores flying red Juneteenth flags alongside the American flag reminded me of the solidarity people show to communities in need. My journey had come to an end outside of a Cathedral, at the Courthouse. I was tired at the Joshua Glover Historical Marker. I noted the year it went up—2001—and silently thanked the person responsible for recognizing this story during another tumultuous time for the country.
The throbbing sensation in my shins, annoying bug bites, and other fun things that come with physically pushing a body to its limits will eventually fade away. However, the deep appreciation I gained for those who emancipated themselves and traveled up north in pursuit of freedom will never leave me. For the vast majority of the trip, I moved in silence. No music, audiobooks, or other entertainment. I wanted to move in silence, like those before me. I still have much to unpack regarding the lessons I learned on my trek, but I’m satisfied with what I found in my soul on the way.
Before I took the first step, I was immediately supported by friends and friends, which filled me with the confidence and accountability to embark on my journey. Today, threats come from all sectors of government, including Interior Secretary Burgum, who is trying to erase Black and brown history on America’s public lands. It’s easier to defend progress and overcome physical pain when you’re surrounded by love and a conviction in purpose.
