Young Frederick Douglass

In 1826 at age 8, Douglass was sent to live and work in the Fells Point neighborhood of Baltimore, where he served as caretaker and companion for a younger White boy, Thomas Auld. He joined Thomas for lessons in reading and writing taught by his mother, Sophia.

Frederick’s attendance was abruptly halted when Sophia’s husband, Hugh Auld, found out about the shared lessons. Auld told his wife that education would “spoil a slave.” Besides, teaching a slave to read and write was against the law in Maryland and most other southern states. But by then, Frederick had caught the learning bug and he continued to learn on his own, secretly borrowing Thomas’s schoolbooks and even trading food with White boys on the streets for help with lessons.

In August 1832, when Frederick was about 13 or 14, he was sent back to the Shore to St. Michael’s. His original enslaver having died, Frederick was now enslaved by Thomas Auld, uncle of the boy he had served in Fells Point. This Auld was well-known as a hard, often abusive enslaver. A strong and hard worker, Douglass had also become a resentful and rebellious teenager and wanted to be free.

Six months after his return, in January 1833, Douglass’s labor was leased to a local farmer, Edward Covey. Known as a “slave breaker,” Covey used harsh physical and psychological treatment to break the spirit of an enslaved worker.

It didn’t work that way with Douglass, who endured months of mistreatment, including frequent beatings. One day when Covey began beating him, Douglass fought back. After a two-hour struggle, Douglass prevailed and Covey never laid hands on him again.

In January 1834, Douglass was sent to work on the nearby William Freeland farm where conditions were better. There he used his free time to start a Sabbath school and secretly taught local Blacks to read and write. Still determined to gain his freedom, he and four other enslaved workers made plans to escape by canoe to Pennsylvania. Unfortunately, their plans were discovered and all four were arrested. After a short incarceration, Douglass, instead of suffering the common fate for rebellious enslaved workers of being “sold South,” was sent back to live again with Hugh and Sophia Auld in Baltimore.

There Douglass learned the craft of ship caulking and was hired out to shipyards. At first the Aulds took his wages and gave Douglass a small portion to keep as his own. Later, Douglass was allowed to hire himself out, giving a set amount weekly to the Aulds and paying for his own food and clothes.

With this increased liberty of movement and some limited economic freedom, Douglass began to spend time in the local Black community where he met a freeborn Black woman, Anna Murray. In September 1838, she helped him escape to freedom in the North and his days as an enslaved worker were over.

Murray joined him shortly after his self-liberation and the two were married in New York. Family tradition says that Murray sold her feather bed to help pay for Douglass’s passage North.

The newlyweds soon left for Massachusetts where it was safer for formerly enslaved people than in “slave-catcher” infested New York City. It was in New Bedford that Frederick Bailey shed his alias, “Frederick Johnson,” and took the name under which he would become a famous orator, founder of three newspapers, writer of three autobiographies, and a life-long civil rights advocate. His adopted surname, “Douglass,” was inspired by Sir Walter Scott’s poem, The Lady of the Lake. In the poem, “Douglass” was “an exiled nobleman.”

Though not all the dangers to his liberty were over, at age 20 Frederick Douglass was free to begin charting his own direction in life.



The Frederick Douglass Driving Tour starts at Frederick Douglass Park on the Tuckahoe River near his birthplace. In the park are outdoor exhibits depicting his early years with his grandparents and cousins.

In nearby Easton, a statue of Douglass stands in front of the Talbot County Courthouse where Douglass gave his famous “Self-Made-Man Speech” in 1878. Then visit the nearby old Talbot County Jail House where Douglass was held after his first failed escape attempt over 50 years earlier in the 1830s.

Head to St. Michael’s where the 15-year-old Frederick started a secret school for Black people. You can stay at the Dr. Dodson House B&B, previously the home of the daughter of Douglass’s former enslaver Thomas Auld. Several years after the Civil War, Douglass was welcomed as an honored guest at the daughter’s home.

Also in St. Michael’s is the Chesapeake Bay Maritime Museum which includes the Mitchell House where Frederick Douglass’s sister, Eliza Bailey Mitchell, lived. It is an excellent example of the home of a free middle-class Black family. Eliza’s husband, Peter Mitchell, was born enslaved but was later freed due to Quaker influence on the owner’s family. As a freed man in 1836, Mitchell “bought” his wife Eliza and their two children for $100. After the Civil War, Douglass would visit his sister and family there.

The St. Michael’s Museum offers a Frederick Douglass Walking Tour on the 2nd and 4th Saturday every month from May through October.

The driving tour continues to follow Douglass’s history, winding through the Eastern Shore then on to Annapolis, Baltimore, and Washington, D.C., where Douglass lived and worked in his later years. In most places, self-guided walking tours and/or docent-led tours are available.

Despite the hardships of his early years in Maryland, Douglass felt a strong love and kinship for the Eastern Shore. Here is a quote from Douglass about his ties to Maryland.

“I am an Eastern Shoreman, with all that name implies. Eastern Shore corn and Eastern Shore pork gave me my muscle. I love Maryland and the Eastern Shore!

Jane Jewell is a writer, editor, photographer, and teacher. She has worked in news, publishing, and as the director of a national writer's group. She lives in Chestertown with her husband Peter Heck, a ginger cat named Riley, and a lot of books.