On the Trail of the Ancestors: A Black Cowboy’s Ride Across America

A Guest post by Lisa K. Winkler

February is Black History Month.

If you’re looking for a fast, informative and entertaining book, please check out my book: On the Trail of the Ancestors: A Black Cowboy’s Ride Across America.

I am a former middle school Language Arts teacher and a writer. I met Miles Dean when I served as a literacy consultant in Newark, NJ public schools. When I heard how he rode his horse across the United States to celebrate and honor the contributions of African Americans to the country’s exploration and development, I was immediately hooked. I knew his story would be a great read for our students as well as adults. I interviewed Miles about his journey and researched the geography he traversed, and the history he honored, including the role of African American cowboys, black jockeys, black abolitionists, Buffalo Soldiers and Deputy US Marshals.

Becoming a cowboy was a big dream of Dean’s. Growing up in Brooklyn, New York, Dean first learned about cowboys from watching television. Like any boy at that time, he wanted to be like those heroes and pretended to be a cowboy. He galloped through the streets on his bicycle, ambushing outlaws on street corners. However, none of the cowboys he saw were African-American. At age 23, he saw the late Sidney Poitier play a cowboy in the 1972 film, Buck and the Preacher, and realized he too could be a black cowboy. The film inspired him to explore the African American history he never learned in school, specifically the contributions made during the 1500-1800s when horses were the primary means of transportation. He knew he wanted to make a cross-country journey and retrace the steps of these early pioneers; it was just a question of when.

Black Cowboy's Ride Across America book cover
Black Cowboy’s Ride Across America by Lisa K. Winkler

On September 22, 2007, Dean, 57, brought his horse, Sankofa, an Arabian stallion into New York City and rode to the African Burial Grounds, in lower Manhattan to begin his journey. Granted an unpaid leave of absence from his 5th grade social studies position, he embarked on this odyssey he had dreamed about for nearly 35 years. He finally traveled like a black cowboy!

Six months later, Dean completed the trip with a celebration at the California African American Museum in Los Angeles. In between he visited several historical monuments, paying homage to history’s forgotten heroes, including the black jockeys at Kentucky’s Churchill Downs and soldiers at Tennessee’s African American Civil War Cemetery. His travels through Memphis and Little Rock evoked his own memories of growing up during the Civil Rights Movement. His ride through the harsh deserts of the Southwest and across California’s formidable Chocolate Mountains allowed him to re-enact the conditions and perils faced by early cowboys and marshals, both white and African American.

On the Trail of the Ancestors: A Black Cowboy’s Ride Across America recounts how one man followed his childhood dream. Dean’s commitment to his journey helped him battle a brain tumor; his gratitude to his ancestors fortified his resilience; and his integrity to honoring heroes in history via his horse kept him on road. During his six-month, 5,000-mile journey, Dean addressed people at schools and colleges, community organizations, and penal institutions. He met hundreds of Americans through informal encounters at campgrounds, Walmart parking lots, restaurants, and country stores. With each, he shared his reasons for the journey and inspired others to fulfill their dreams.

As Dean travels atop his horse from state to state, the reader learns about African Americans who contributed to US history. Dean’s relationship with his horse Sankofa provides insights about what it is like to ride a horse for six months. Whether navigating dangerous terrain or city traffic, riding long distances, handling medical problems for him and the horse, or facing the challenges of acquiring the four relief horses, his anecdotes regale readers with the visceral pleasures and difficulties of such a journey. Dean’s story of making his dream to become a cowboy a reality demonstrates that an ordinary person can accomplish the extraordinary.

The 2021 Netflix film, The Harder They Fall is loosely based on real African American cowboys, lawmen, and outlaws of the 19th-century American West. Among them, Nat Love, Bill Pickett and Bass Reeves in my book.

I also wrote an Educators’ Guide that can be used by teachers and parents alike. The guide includes cross-disciplinary activities in writing, art, drama, geography, math and a character education platform,  “The Horseman’s Creed.”

Here’ is a short excerpt from On the Trail of the Ancestors: A Black Cowboy’s Ride Across America.

Excerpt from:  Ch. 2 The Journey Begins

In the wee hours of the morning, the sun not yet warming the day, Miles walked to his barn and greeted Sankofa with the familiar whinny he had perfected during their years together.  The 12- year-old stallion whinnied back as if to say he knew the big day had come…

…Miles loaded Sankofa into the trailer for the 40 -minute drive from his New Jersey ranch through the Holland Tunnel to lower Manhattan.  When they arrived, Miles mounted Sankofa to ride horseback to the African Burial Ground, nearly two miles away.

Uncovered during an excavation in 1991, the 200-year-old graveyard lies beneath an area of about five city blocks north of City Hall. The construction of a new federal office building had been halted to allow archeologists and other scientists to dig out the skeletal remains of more than 400 men, women, teenagers and children. Further exploration revealed artifacts of the skeletons’ cultures: buttons, beads, coins, rings, tobacco pipes, and nails.

It all proved that slavery in New York dated back to 1626, when the Dutch East India Company entrapped Africans from their homes – jungles, savannas, deserts, and villages- destroying tribes and families. Packed into ship holds below sea level, they endured illness and starvation, and then faced harsh winters and unending labor. Slaves cleared land, built forts, mills, houses, constructed roads, and dug ditches. They slept in attics and on farms, cultivating gardens, preparing food and serving both as domestics and as waiters in taverns. Many assisted crafts men; employing the skills they learned in Africa…

…Miles had invited Kamau Kallifoni, a Yoruba priest to offer libation to the ancestors. The religion of the Yoruba people, predominantly from Nigeria and Benin, represents 1,000- year-old traditions of reverence for nature and forefathers.

The group formed a circle around the priest who wore a black and brown patterned dashiki. Goliath in size and demeanor, he commanded attention and respect as he dripped a few drops of water on the ground and chanted blessings praising the ancestors both in English and an African dialect. He chanted, “What I have in my hand is water, the most substantial element in life. We take this water and hold it up, and the god we call by thousands of names, we ask that god that we serve to look down upon us.”

Shortly after, a light rain fell, moistening faces and the street. Miles felt the ancestors were sending him a message, as if answering the libation with one of their own.  “These ancestors’ struggles got me where I am today- embarking on a cross-country journey as a free man,” he later said.


I hope you’ll add On the Trail of the Ancestors: A Black Cowboy’s Ride Across America to your reading list. I’d be delighted to hear from you.

Here’s a YouTube trailer created about the book:

A Black Cowboy’s Ride book trailer

3 thoughts on “On the Trail of the Ancestors: A Black Cowboy’s Ride Across America

  1. Liz Dexter says:

    This looks very interesting, and I’m pleased to see I can get hold of it in the UK, too. I’ve added it to my wish list for the time being. Good luck with it!

  2. prairiehousebooks says:

    Love the description of this book and of an overlooked part of American history. The Eiteljorg Museum in Indianapolis has done presentations on this topic, and they have one coming up on Feb. 17 2022. Their annual Leon Jett Memorial Lecture is dedicated to the subject of Black Cowboys.
    Unfortunately, it is not virtual this year, but for anyone in the Indy area who feels comfortable venturing out…


Leave a Reply