Illustration of Dominique Jackson on her jeep in front of her road trip map

I Road Tripped Around the Midwest Solo — Here's What I Learned As a Black Woman

Seven years ago, I left the country for the first time for a two-week study abroad trip to Dublin, Ireland. I was 21 years old. Since then, many travels have shaped my worldview, leading me to where I am today — a digital nomad with the goal to hop across the world for one year.

When I reflect on my past trips, I see that one, in particular, ignited in me the confidence to travel solo: a road trip across the Midwest. In September 2020, I road-tripped around part of the region to cover and amplify Black-owned business. At the time, road trips were gaining popularity due to the ongoing pandemic, and it felt like the safest way to travel.

The plan was to head out alone for the first time and uncover historical landmarks along the way. But as with most trips, I discovered things that only the road could reveal. As a Black woman, I was inspired to take a road trip after learning about the "The Negro Motorist Green Book," which was published between 1936 and 1967. It served as a travel guide for African Americans, documenting safe lodgings, restaurants, and gas stations. I felt as if I was doing my own version of the "Green Book," as I slept and ate in and explored Black-owned and operated establishments.

A quote card from Dominique Jackson
Courtesy of Kaitlyn Collins

As a woman traveling solo, I had my fears: insecurities about planning all the logistics, worries over getting pulled over by the cops, and doubts on whether or not I would be able to complete such a long trek alone. Nevertheless, I covered five cities in roughly a week and a half.

With each destination, I arrived at a new version of myself. I tend to second-guess myself, but making every decision while on the road allowed me to trust my voice — and slow down.

Illustration of Dominique Jackson's road trip map
Courtesy of Kaitlyn Collins

Kicking off my trip, I went from Columbus, Ohio, to Cleveland. Most of my family lives in the latter, but I had never seen the city as I did on this trip. During my time here, I ate at Black-owned restaurants like Sauce the City, Cleveland Cold Brew, and The Vegan Doughnut Company.

I also woke up to catch the sunrise and went hiking in Cuyahoga Valley National Park. Watching the sunrise from different parts of the globe has now become a hallmark in my travel routine; it starts my day in thankfulness and gratitude. With so many demands as a Black woman, from career to relationships, taking a moment to ground myself in the present has taught me to navigate my days from a place of peace.

A road going through Cuyahoga Valley National Park, Ohio,
Karla Ann Cote/Getty Images

My time in Cleveland would not have been complete without a visit to Chateau Hough, an urban winery located in the city's Hough neighborhood. Their goal is to produce opportunities for economic development. As I enjoyed wine tasting and a tour of the fields, I saw that communities were thriving through innovative people who were creating solutions for a new future even amid trying times.

Hopping into my car, I headed to my next stop: Detroit. Two of the main places I visited in the Motor City were the iconic Motown Museum and the Charles H. Wright Museum of African American History. As I toured the former, I felt as if I had been transported back in time, standing where musical pioneers created history.

Motown Museum (Hitsville U.S.A.), original home of Motown Records in Detroit, Michigan
Raymond Boyd/Getty Images

At the Charles H. Wright Museum of African American History, I reflected on the past and was simultaneously hit with the current future for Black Americans. While exploring the museum, the notifications on my phone lit up as Breonna Taylor's case verdict came rushing in. On this day, it was announced that the police officer would not be charged with murder but for the bullets that missed her. I was not shocked, nor surprised. But I stood there in grief as I thought about Taylor's life and how it was lost. As a Black woman, I don't often feel safe navigating this world, no matter where I am, but to not feel safe in one's home is a level of grief I'm still processing.

A quote card from Dominique Jackson
Courtesy of Kaitlyn Collins

Even though I was on the road alone, my phone rang that day from friends who wanted to process the verdict together. It was then that I learned I am never truly alone and that community matters.

As I said goodbye to Detroit, I couldn't help but be grateful for my time in the city. I was also able to see firsthand the meaning of "reach as you climb" come to fruition when I stopped at Détroit Is the New Black, a retail space featuring Black designers and creatives. On the day I popped in, owner Roslyn Karamoko was teaching a class in the back of the store to youth looking to learn more about the fashion industry. Detroit is a city all about legacy, and it's easily seen through the people, past and present, who live there. I contemplated how much mentorship has personally allowed me to walk into rooms I never thought possible and opened up doors to incredible relationships and opportunities.

The longest stretch on my road trip was five hours to Wisconsin. I never had that much time on the road by myself. Not only was the drive picturesque, but it was also peaceful and permitted self-reflection. I listened to audiobooks, podcasts, and music.

During the drive, I reflected on my life — 20-something, single, working in my dream career, and hitting the road solo. Most of the time, many of us, including myself, tend to rush to the next thing without pausing to note where we are currently. My road trip gave me the opportunity to stop and slow down. Rather than rushing and overthinking, I found peace in my solitude on the road.

One of my first stops was the Wisconsin Black Historical Society, which documents and preserves the historical heritage of African descent in the state. The museum, which has been opened for more than 30 years, is currently the only institution in the state with a keen focus on preserving African American history in Wisconsin. I toured the museum with founding director Clayborn Benson III, who shared some hyperlocal history about African Americans who settled in Wisconsin. It was my first time in the city, and I learned a lot about the unsung heroes who pushed our country forward.

Exterior of Sherman Phoenix
Courtesy of Sherman Phoenix

Beyond the museum, one of my favorite places in Milwaukee was Sherman Phoenix, a hub for entrepreneurship and creativity. This market is filled with Black-owned businesses, from restaurants and clothing stores to a copyediting company. I spent the afternoon here, exploring and chatting with the owners. As I spoke to one of the workers, she described her job as a safe haven — she loved being able to work in a place that valued Black excellence. This showed me the importance of creating spaces that are unapologetically Black.

A quote card from Dominique Jackson
Courtesy of Kaitlyn Collins

At about this time, I had been on the road for roughly one week. Next, I drove down to Chicago. The Windy City has a special place in my heart as I spent my college years running around the South Loop.

It was one of the few times I traveled back to Chicago since my graduation. While there, I reflected on how far I've come. It was nostalgic for me to return to a place I once called home.

Dr. C. Siddha Webber's 'Have A Dream' mural is displayed in the Bronzeville neighborhood in Chicago, Illinois
Raymond Boyd/Getty Images

Being in Chicago again showed me that I could see my dreams come to pass with time and patience. While there, I explored the Bronzeville neighborhood, which is also known as the "Black Metropolis," or the "Black Belt," and I wandered through historical landmarks such as Nat King Cole's residence, vibrant art galleries, and churches.

Aerial viewof Madam Walker Legacy Center
Courtesy of Madam Walker Legacy Center

Wrapping up my nearly two-week-long road trip across the Midwest, I ended my journey in Indiana, where I visited the Madam Walker Legacy Center, named after Madam C.J. Walker. I mainly knew of her as America's first self-made female millionaire, but discovered that she's so much more. It was encouraging to learn about Walker and how she paved the way for female entrepreneurs.

As I drove back to my hometown of Columbus, Ohio, I felt a deep sense of gratitude for my road trip, all the places I had seen, and the people I met along the way. This journey showed me that I can step outside my comfort zone, travel solo, and see ordinary places from an extraordinary perspective.

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