Black History Tours on the Eastern Shore, Part 1

Jane Jewell • July 17, 2023

Young Frederick Douglass


Frederick Douglass and Harriet Tubman — two of history’s most famous African Americans — were born and lived their early years on the Eastern Shore of Maryland. Both escaped from slavery, adopting new names in part to hide from “slave catchers.” Both became activists for freedom and civil rights for their fellow African Americans before, during, and after the Civil War. 

 

Today, with the help of self-guided or docent-led walking and driving tours, you can visit the sites where Douglass and Tubman lived and worked before escaping North to freedom. Sites are open to the public or visible from the road. The Eastern Shore is a beautiful rural area and a drive to these sites can be relaxing and inspiring.

 

Part 1 of this series focuses on abolitionist, orator, writer, and newspaper publisher Frederick Douglass. Part 2 will cover Underground Railroad conductor, Civil War spy and nurse, and women’s rights advocate Harriet Tubman.

 

Frederick Douglass (1818-1895) — originally named Frederick Augustus Washington Bailey — was born enslaved on the Holmes Hill Farm on Tuckahoe Creek in Talbot County, just south of Hillsboro. Douglass was raised with several other enslaved children by his grandmother, Betsy Bailey. His mother, Harriet Bailey, was enslaved on a plantation a dozen miles away. Douglass later said that he only remembered seeing his mother a few times before she died when he was about 7.

 

Douglass said in his early writings that his mother’s White enslaver, Aaron Anthony, was likely his father, but he later stated that he couldn’t confirm who his father was.



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.

 

Common Sense for the Eastern Shore

By CSES Staff October 24, 2025
 Sparking alarm among housing advocates, social workers, and residents, Salisbury Mayor Randy Taylor has announced plans to gut Salisbury’s nationally recognized Housing First program, signaling a break from years of bipartisan progress on homelessness. Created in 2017 under then-Mayor Jacob Day, the initiative was designed around a simple but powerful principle: that stable, permanent housing must come first before residents can address problems with employment, health, or recovery. The program was designed to provide supportive housing for Salisbury’s most vulnerable residents — a model backed by decades of national data showing it reduces homelessness, saves taxpayer dollars, and lowers strain on emergency services. But under Taylor’s leadership, that vision appears to be ending. In a letter to residents, the City of Salisbury announced that the Housing First program will be shut down in 2027, in effect dismantling one of the city’s long-term programs to prevent homelessness. Taylor says he plans to “rebrand” the program as a temporary “gateway to supportive housing,” shifting focus away from permanent stability and toward short-term turnover. “We’re trying to help more people with the same amount of dollars,” Taylor said. Critics call that reasoning deeply flawed, and dangerous. Former Mayor Jacob Day, who helped launch the initiative, says that Housing First was always intended to be permanent supportive housing, not a revolving door. National studies show that when cities replace permanent housing programs with short-term placements, people end up right back on the streets, and that costs taxpayers more in emergency medical care, policing, and crisis intervention. Local advocates warn that Taylor’s move will undo years of progress. “This isn’t just a policy shift, it’s a step backward,” one social service worker said. “Housing First works because it’s humane and cost-effective. This administration is turning it into a revolving door to nowhere.” Even some community partners who agree the program needs better oversight say that Taylor is missing the point. Anthony Dickerson, Executive Director of Salisbury’s Christian Shelter, said the city should be reforming and strengthening its approach, not abandoning its foundation. Under Taylor’s proposal, participants could be limited to one or two years in housing before being pushed out, whether or not they’re ready. Advocates fear this change could push vulnerable residents back into instability, undoing the progress the city was once praised for. While Taylor touts his plan as a way to “help more people,” critics say it reflects a troubling pattern in his administration: cutting programs that work. For years, Salisbury’s Housing First initiative has symbolized compassion and evidence-based leadership and has stood as a rare example of a small city tackling homelessness with dignity and results. Now, as Taylor moves to end it, residents and advocates are asking a simple question: Why would a mayor tear down one of Salisbury’s most successful programs for helping people rebuild their lives?
By John Christie October 24, 2025
On the first Monday of October, the Supreme Court began a new term, Term 2025 as it is officially called. The day also marked John Roberts’ 20 years as Chief Justice of what history will clearly record as the Roberts Court. Twenty years is a long time but at this point, Roberts is only the fourth longest serving Chief Justice in our history. John Marshall, the fourth and longest, served for 34 years, 152 days (1801–35). Roger Brooke Taney, served for 28 years, 198 days (1836–64). Melville Fuller, served 21 years, 269 days (1888 to 1910). John Roberts was originally nominated by George W. Bush to fill the seat held by the retiring Sandra Day O’Connor but, upon the unexpected death of William Rehnquist, Bush instead nominated Roberts to serve as Chief Justice. His nomination was greeted by enthusiasm and high hopes in many quarters. He was young, articulate, personable, and highly qualified, having had an impressive academic record, experience in the Reagan administration and the private bar, and service on the federal D.C. Court of Appeals for two years. His “balls and strikes” comment at his confirmation hearing struck many as suggesting judicial independence. He sounded as well very much like an institutionalist, having said at an early interview that “it would be good to have a commitment on the part of the Court to act as a Court.” Whatever else might be said 20 years later about the tenure of John Roberts as Chief Judge, the Supreme Court is no doubt much less popular and much more divisive today than it was on September 29, 2005, when he was sworn in as the 17th Chief Justice by Justice John Paul Stevens, then the Court’s most senior associate justice, and witnessed by his sponsor, George W. Bush. Gallup’s polling data shows popular support for the Court now at the lowest levels since they started measuring it. In July 2025, a Gallup poll found that, for the first time in the past quarter-century, fewer than 40% of Americans approved of the Supreme Court’s performance. According to Gallup, one major reason that approval of the Supreme Court has been lower is that its ratings have become increasingly split along party lines — the current 65-point gap in Republican (79%) and Democratic (14%) approval of the court is the largest ever. The legal scholar Rogers Smith wrote in The Annals of the American Academy of Political and Social Science in June, “Roberts’s tenure as Chief Justice has led to the opposite of what he has said he seeks to achieve. The American public now respects the Court less than ever and sees it as more political than ever.” These results signify more than simply a popularity poll because a Court without broad public support is a Court that will not have the same public respect upon which their most important decisions have historically depended. And, whatever the reasons for this development, it has happened on John Roberts’s watch. There is no better example of the current divisiveness on the Court than the remarkable string of “emergency” rulings on the Court’s so-called shadow docket since January 20. The extent of ideological and partisan differences has been sharp and extreme. The conservative majority’s votes have frequently been unexplained, leaving lower court judges to have to puzzle the decision’s meaning and leaving the public to suspect partisan influences. And the results of these shadow docket rulings have had enormous, sometimes catastrophic, consequences: Removing noncitizens to countries to which they had no ties or faced inhumane conditions Disqualifying transgender service members Firing probationary federal workers and independent agency heads Ending entire governmental departments and agencies without congressional approval Allowing the impounding of foreign aid funds appropriated by Congress Releasing reams of personal data to the Department of Government Efficiency Allowing immigration raids in California based on racial and ethnic profiling John Roberts has written many Supreme Court opinions in his 20 years as Chief Justice. At the 20-year mark, the most important, to the nation and to his legacy, will likely be his opinion in the Trump immunity case, which changed the balance of power among the branches of government, tipping heavily in the direction of presidential power. Trump v. United States (2024). In her dissent from his majority opinion in that case, Justice Sonia Sotomayor, joined by Justices Elena Kagan and Ketanji Brown Jackson, warned about the consequences of such a broad expansion of presidential power. “The Court effectively creates a law-free zone around the president,” upsetting the status quo that had existed since the nation’s founding and giving blanket permission for wrongdoing. “Let the president violate the law, let him exploit the trappings of his office for personal gain, let him use his official power for evil ends. In every use of official power, the president is now a king above the law.” Roberts claimed in his majority opinion that the “tone of chilling doom” in Sotomayor’s dissent was “wholly disproportionate” to what the ruling meant. However, Sotomayor’s words have proved prescient: the breadth of power that Trump and his administration have asserted in the months since he was sworn in for his second term has made plain how boundlessly they now interpret the reach of the presidency in the wake of the Roberts opinion. Despite the early “balls and strikes” comment, the assessment of John Roberts’ long term judicial record suggests something different as seen by several distinguished legal commentators from significantly different perspectives. As summarized by Lincoln Caplan, a senior research scholar at Yale Law School, in a new retrospective article on Robert’s 20-year tenure, “From his arrival on the Court until now, his leadership, votes, and opinions have mainly helped move the law and the nation far to the right. An analysis prepared by the political scientists Lee Epstein, Andrew Martin, and Kevin Quinn found that in major cases, the Roberts Court’s record is the most conservative of any Supreme Court in roughly a century.” “What Trump Means for John Roberts's Legacy,” Harvard Magazine , October 8, 2025. Steve Vladeck, Georgetown Law Center professor and a regularly incisive Court commentator, characterized the 20-year Roberts’ Court as follows: “The ensuing 20 years has featured a Court deciding quite a lot more than necessary — inserting itself into hot-button social issues earlier than necessary (if it was necessary at all); moving an array of previously settled statutory and constitutional understandings sharply to the right; and, over the past decade especially, running roughshod over all kinds of procedural norms that previously served to moderate many of the justices’ more extreme impulses.” “The Roberts Court Turns Twenty,” One First , September 29, 2025. In another remarkable new article by a widely respected conservative originalist, similar concerns about the present Court have very recently been expressed. Caleb Nelson, who teaches at the University of Virginia and is a former law clerk to Justice Clarence Thomas, has written that the text of the Constitution and the historical evidence surrounding it in fact grant Congress broad authority to shape the executive branch, including by putting limits on the president’s power to fire people. “Must Administrative Officers Serve at the President’s Pleasure?” Democracy Project, NYU LAW , September 29, 2025. When the First Congress confronted similar ambiguities in the meaning of the Constitution, asserts Nelson, “more than one member warned against interpreting the Constitution in the expectation that all presidents would have the sterling character of George Washington.” Nelson continues, “The current Supreme Court may likewise see itself as interpreting the Constitution for the ages, and perhaps some of the Justices take comfort in the idea that future presidents will not all have the character of Donald Trump. But the future is not guaranteed; a president bent on vengeful, destructive, and lawless behavior can do lasting damage to our norms and institutions.” John Christie was for many years a senior partner in a large Washington, D.C. law firm. He specialized in anti-trust litigation and developed a keen interest in the U.S. Supreme Court about which he lectures and writes. 
By Jan Plotczyk October 24, 2025
If you’ve ever wondered just how slavishly loyal Rep. Andrew P. Harris (R-MD01) is to President Donald Trump, you can now put a number on it! Just consult the Republican National Platform Ratings. When you do, you will find that Rep. Harris has a very high overall score: 90.38%. He is the most aligned with the Trump/GOP platform among Maryland’s congressional representatives. No surprise there. Among all U.S. senators and representatives (using 2024 votes), Harris is 43rd most aligned. One might expect more from the chair of the right-wing Freedom Caucus. Harris scores at 90.38% aligned overall. His ratings by topic range from 82.98% to 100%. The topics refer to chapters in the platform: Defeat inflation and quickly bring down all prices. Seal the border and stop the migrant invasion. Build the greatest economy in history. Bring back the American Dream and make it affordable again for families, young people, and everyone. Protect American workers and farmers from unfair trade. Protect our Constitution and seniors. Cultivate great K-12 schools leading to great jobs and great lives for young people. Bring common sense to our government and renew the pillars of American civilization. Government of, by, and for the people. Return to peace through strength. Here are all Harris’s scores:
By CSES Staff October 24, 2025
Several thousand people turned out on Oct. 18 in communities across the Eastern Shore to participate in the national “No Kings Day” protests, joining thousands of simultaneous events nationwide opposing the policies of President Trump’s administration. Demonstrations were held in Salisbury, Ocean City, Easton, Cambridge, Chestertown, and Centreville. These gatherings were part of a broader coalition effort that organizers say reflects frustration with the administration’s direction and a demand for renewed accountability and democracy. Participants across the Shore held signs and expressed concerns about immigration enforcement, executive power, and transparency in government. In jurisdictions that lean Republican and supported Trump in 2024, the rallies underscore a growing discrepancy between voting patterns and present activism. For example, in Queen Anne’s County — where the Trump vote was strong — residents joined the demonstration with statements of surprise at the turnout. Despite the scale of national mobilization, local organizers emphasized that the protest is rooted in community values of fairness, participation, and civic voice. One organizer on the Shore described the event as a reminder that “when people choose to show up, they remind their communities what democracy looks like.” Authorities reported no major disruptions during the Shore events, and police in some areas confirmed the rallies proceeded peacefully. For many in the region, the demonstrations mark an opening moment for more active civic engagement on the Shore, one that observers say could reshape local politics in counties historically seen as less partisan.
By CSES Staff October 24, 2025
The Maryland Democratic Party has launched a statewide initiative, Contest Every Seat, that aims to recruit candidates to run for public office across all levels of government ahead of the 2026 elections. Party officials say the goal is to ensure voters in every district across Maryland have a choice on the ballot. The program will include outreach, training sessions, and support for prospective candidates considering campaigns for local, county, and state positions. “The effort is designed to encourage Marylanders who want to make change in their communities to step up and take action,” the party announced. Interested individuals can visit mddems.org/run for information about the application process and training opportunities. The Maryland Democratic Party said similar initiatives in past election cycles helped increase candidate recruitment in local and rural areas, including the Eastern Shore.
By CSES Staff October 24, 2025
With the federal government now shut down for more than three weeks, Maryland is losing hundreds of thousands of dollars in revenue daily, a reflection of the state’s deep economic ties to the federal workforce. According to the Maryland Comptroller, approximately 230,000 Marylanders work directly for the federal government, with an additional 200,000 employed by federal contractors. The state’s economy, long intertwined with the operations of nearby federal agencies, is feeling the strain as paychecks stall and agencies close. Comptroller Brooke Lierman estimates Maryland is losing about $700,000 in state revenue each day — roughly one percent of the state’s average daily revenue of $100 million. “That is a small piece of our overall state budget,” Lierman said, “but as long as all our federal workers are paid what they are owed, that money will get back to us.” Federal employees generally receive back pay after shutdowns end, but recent statements from President Trump suggesting that furloughed workers may not be repaid have created uncertainty. More than 150 members of Congress, including Maryland’s entire Democratic delegation, signed a letter this week urging the Trump administration to guarantee back pay under the 2019 Government Employee Fair Treatment Act, which requires compensation for federal employees affected by a shutdown, and which Trump himself signed into law. Rep. Sarah Elfreth (D-MD03) said Congress is prepared to defend those protections. “Denying that pay would be illegal, and we will use every tool we have — both in Congress and in the courts — to ensure federal employees are made whole,” she said. During the 35-day federal shutdown in 2019, Maryland lost more than $13 million daily in economic activity and over $550,000 daily in tax revenue, according to state data. This latest shutdown comes amid broader federal workforce reductions under the U.S. Department of Government Efficiency, which announced layoffs earlier this year. A federal judge temporarily halted further cuts on Oct. 15 following a legal challenge. The effects extend beyond government offices. Universities such as Johns Hopkins and the University of Maryland Baltimore Washington Medical Center report disruptions to federally funded research projects and grant cycles. Gov. Wes Moore has directed state agencies to provide emergency support to furloughed federal workers, including housing and utility assistance. On Oct. 17, Moore announced the Maryland Transit Administration will offer free MARC and commuter bus rides to federal employees who show valid government ID. “This is what Maryland does in times of crisis, we band together and help each other out,” Moore said. “But no state can fill the gap created by the federal government. The longer this shutdown lasts, the more pain we will feel.” There is no indication of when negotiations in Washington to end the shutdown will resume.
Show More