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 John Christie March 3, 2026
Just up the road from Maryland’s Eastern Shore lies Independence National Historical Park in Philadelphia. Administered by the National Park Service (NPS), the park is dedicated to the preservation of historical structures and properties associated with the American Revolution and the founding and growth of the United States. The centerpiece of the park is Independence Hall, where the Declaration of Independence and the United States Constitution were debated and adopted by America's Founding Fathers in the late 18th century. Nearby is the Liberty Bell, an iconic symbol of American independence, displayed in the Liberty Bell Center. In the park as well is what’s called the President’s House, an exhibit on the site of the first official residence of the president of the United States. President Washington occupied the Philadelphia President's House from 1790 to 1797. His successor, John Adams, lived there from 1797 to 1800. Although the original structure no longer exists, the exhibit includes a view of the foundation of the house where our first two presidents lived with their families. Research has turned up information about nine enslaved Africans owned by Washington and brought to Philadelphia’s presidential residence during his time there. To commemorate the lives of those slaves, their names are etched in a wall in the exhibit: Oney Judge, Austin, Christopher Sheels, Giles, Hercules Posey, Joe Richardson, Moll, Paris, and Richmond. The site includes exhibits on how their struggles for freedom represented this country’s progress away from the horrors of slavery and into an era where the founding ideals of “Life, Liberty and the pursuit of Happiness” could be achieved for every American. An intended theme of the President’s House exhibit is “Liberty: The Promises and Paradoxes.” “The promises of liberty and equality granted in the founding documents present a paradox: not only were they ideals to strive for but they were unfulfilled promises for people who struggled to be fully included as citizens of our nation.” ------------------------------------------------------------ On March 27, 2025, President Trump signed Executive Order 14253, “Restoring Truth and Sanity to American History.” EO14253 stated in part: “Over the past decade, Americans have witnessed a concerted and widespread effort to rewrite our nation's history, replacing objective facts with a distorted narrative driven by ideology rather than truth.” In order to “restore truth in American history,” EO14253 directed the Secretary of the Interior to ensure that all public monuments, memorials, or similar properties within the Department of the Interior's jurisdiction do not contain descriptions or other content that “inappropriately disparage” Americans past or living (including persons living in colonial times) and instead focus on the greatness of the achievements and progress of the American people. In response to this order, on January 22, 2026, the NPS suddenly removed 34 educational panels and video exhibits that referenced slavery and provided information about the individuals enslaved at the President’s House. The day these exhibits were removed, the City of Philadelphia filed a lawsuit in the federal district court in Philadelphia against Secretary of the Interior Doug Burgum, the Department of the Interior, Acting Director of NPS Jessica Bowron, and the NPS itself, claiming that the removal of the displays was unlawful agency action. On February 16, Judge Cynthia Rufe ordered the Trump administration to restore the slavery-related exhibits at the national park site, holding that NPS lacked the power “to dissemble and disassemble historical truths.” In court, the government asserted it alone had the power to erase, alter, remove, and hide historical accounts on taxpayer and local government-funded monuments within its control. According to Judge Rufe, to claim that “truth is no longer self-evident, but rather the property of the elected chief magistrate and his appointees and delegees, at his whim to be scraped clean, hidden, or overwritten” comes right out of George Orwell’s 1984. In her opinion, no government agency can “arbitrarily” decide what is true, “based on its own whims or the whims of the new leadership.” “It is not disputed that President Washington owned slaves.” Moreover, Judge Rufe determined the removed displays were not mere decorations to be taken down and redisplayed; rather, they were a memorial to the “men, women, and children of African descent who lived, worked, and died as enslaved people in the United States of America.” Each person who visits the President’s House and does not learn of the realities of founding-era slavery receives a false account of this country’s history. Removal of the crucial interpretive materials strips the site of that truth and deprives the public of educational opportunities designed to be free and accessible. For Judge Rufe, the abrupt elimination of historically significant educational material is like “pulling pages out of a history book with a razor.” 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 CSES Staff March 3, 2026
Last month, Megan Outten, candidate for Wicomico County Council District 7, was endorsed by Run for Something (RFS), a national organization that recruits and supports the next generation of progressive leaders for state and local office. The organization’s slate of newly endorsed candidates includes young, diverse progressives from across the country who are ready to lead in their communities. Outten said, “This campaign has always been powered by our community. By parents, teachers, small business owners, and neighbors who know we can do better. Run for Something’s endorsement affirms what we already know here in Wicomico: when everyday people step up to lead, we change what’s possible. Together, we’re building the kind of local government that plans ahead, listens first, and puts families at the center of every decision.” “Bold leaders like Megan are at the forefront of the fight for our rights and freedoms at a time when they have never faced greater threats,” said Amanda Litman, Co-Founder and President of Run for Something. “Run for Something is proud to endorse Megan Outten as part of our latest class of young leaders working to secure lasting change in their communities.” Outten’s platform is rooted in real data and shaped by direct community engagement. With Wicomico now the fastest-growing school system on Maryland’s Eastern Shore, and 85% of students relying on additional resources, she points to the county’s lagging investment as a key area for action. “Strong schools lead to strong jobs, thriving industries, and healthier communities,” Outten said. “Our schools and infrastructure are at a tipping point. We need leadership that stops reacting after things break — and starts investing before they do.” About Run for Something: Amanda Litman and Ross Morales Rocketto launched RFS in January 2017 with a simple premise: to help young, diverse progressives run for state and local offices in order to build a bench for the future. RFS aims to lower the barriers to entry for these candidates by helping them with organization building, connecting them with a robust community, and providing access to the trainings they need to be successful. Since its founding, RFS has helped elect over 1,600 candidates across the country — including 43 candidates in red-to-blue seats in the 2025 election cycle. Today, RFS has the largest database of any Democratic organization, with nearly 80,000 people reaching out since November 2024 with interest in running for office. In total, over 250,000 young people from across the country have signed up to run and gained access to RFS’s resources since the organization launched — a powerful signal that a new generation is showing up to lead.
By Liam Bowman, Capital News Service March 3, 2026
The Trump administration is still arresting immigrants in D.C. without warrants or probable cause despite a judge’s previous ruling that the practice was unlawful, a coalition of immigrant rights groups alleges in a recent court filing. A federal judge ruled in December that the administration’s use of warrantless immigration arrests likely violated federal law and issued a preliminary injunction prohibiting such arrests without probable cause. The ruling was in response to a lawsuit filed by immigrant rights groups and four migrants who were arrested without warrants last year during President Donald Trump’s law enforcement surge in the capital. But federal immigration officials in D.C. are failing to comply with that order, continuing to make warrantless arrests “without the required probable cause determinations,” according to the Feb. 19 motion by plaintiffs. The lawsuit alleges immigration authorities began operating under an “arrest first, ask questions later” policy to comply with arrest quotas imposed after Trump took office last year — and started to ignore the probable cause requirements under immigration law. Click here to read the rest of the article , on the Capital News Service website. The article also details the arrest stories of the plaintiffs who were tricked, and concerns about D.C. police cooperation with immigration authorities. Capital News Service is a student-powered news organization run by the University of Maryland Philip Merrill College of Journalism. For 26 years, they have provided deeply reported, award-winning coverage of issues of import to Marylanders.
By John Christie February 17, 2026
These are the words from Emma Lazarus’ famous 1883 sonnet “The New Colossus” inscribed on a bronze plaque on the pedestal of the Statue of Liberty. In 1990, Congress reaffirmed this vision of America by establishing the Temporary Protected Status program. TPS is designed to provide humanitarian relief to foreign nationals in the United States who come from disaster-stricken countries. In its present form, the TPS legislation gives the Secretary of the Department of Homeland Security responsibility for the program. However, the legislation prescribes the kind of country conditions severe enough to warrant a designation under the statute, the specific time frame for any such designation, and the process for periodic review of a TPS designation which could culminate in termination or extension. All initial TPS designations last from six to eighteen months. Before the expiration of a designation, the statute mandates that the Secretary shall review the conditions in the foreign state to decide if the conditions for the designation continue to be met, following consultation with appropriate agencies of the government. Extension is the default; the designation “shall be extended” unless the secretary affirmatively determines that conditions are “no longer met.” ------------------------------------------------------------- A massive earthquake devastated Haiti in January 2010, and precipitated an unprecedented humanitarian crisis. Shortly after, then-DHS Secretary Janet Napolitano, after consultation with the State Department, designated Haiti for TPS due to “extraordinary conditions.” Haitian nationals in the United States continuously as of January 12, 2010, could thus apply for TPS, and obtained the right to remain and work in the U.S. while Haiti maintained its TPS designation. Napolitano set the initial TPS designation for 18 months. As Haiti’s deterioration worsened, successive DHS secretaries have extended this program. Gang violence and kidnappings have spiked. In 2021, a group of assailants killed Haiti’s then-President Jovenel Moïse. In 2023, another catastrophic earthquake hit Haiti. In 2024, in response to these conditions, then-DHS Secretary Alejandro Mayorkas once again extended and redesignated Haiti for TPS, this time effective through February 3, 2026. During the 2024 election cycle, the GOP candidate, Donald Trump clearly indicated that time had not tempered his views on Haiti, characterized by him as a “shithole country” during his first term. He stated that when elected, he would “absolutely revoke” Haiti’s TPS designation and send “them back to their country.” On December 1, 2025, Kristi Noem, DHS secretary in the second Trump administration, announced, “I just met with the president. I am recommending a full travel ban on every damn country that’s been flooding our nation with killers, leeches, and entitlement junkies. Our forefathers built this nation on blood, sweat, and the unyielding love of freedom, not for foreign invaders to slaughter our heroes, suck dry our hard-earned tax dollars, or snatch the benefits owned to Americans. We don’t want them, not one.” So says the official responsible for overseeing the TPS program. And one of those (her word) “damn” countries is Haiti. Three days before making the above post, Secretary Noem announced she would terminate Haiti’s TPS designation as of February 3, 2026. Five Haitian TPS holders filed suit in federal court in Washington initially seeking an injunction against the termination of the Haitian TPS program pending the completion of the litigation. These plaintiff TPS holders are not “killers, leeches, or entitlement junkies.” They are instead a neuroscientist researching Alzheimer’s disease, a software engineer at a national bank, a laboratory assistant in a toxicology department, a college economics major, and a full-time registered nurse. The case was assigned to district court judge Ana Reyes who granted the plaintiffs’ injunction request on February 2, 2026, by way of an 83-page opinion. The plaintiffs charge that Secretary Noem preordained her termination decision because of hostility to non-white immigrants. According to Judge Reyes, “This seems substantially likely. Secretary Noem has terminated every TPS country designation to have reached her desk — twelve countries up, twelve countries down.” Judge Reyes also decided that Noem’s conclusion that Haiti (a majority non-white country) faces only “merely concerning” conditions cannot be squared with the “perfect storm” of “suffering and staggering” humanitarian toll described in page after page of the record in the case. In Judge Reyes’ view, Noem also ignored Congress’s requirement that she review the conditions in Haiti “after consulting with appropriate agencies.” Indeed, the record indicates she did not consult other agencies at all. Her “national interest” analysis focuses on Haitians outside the United States or here illegally, ignoring that Haitian TPS holders already live here and legally so. And though Noem states that the analysis must include “economic considerations,” Judge Reyes concluded Noem ignored altogether the billions that Haitian TPS holders contribute to the economy. The administration’s primary response in the litigation has been to assert that the TPS statute gives Secretary Noem “unbounded” discretion to make whatever determination she wants, any way she wants. Yes, Judge Reyes acknowledges, the statute does grant Noem some discretion. But, in Judge Reyes’ opinion, “not unbounded discretion.” To the contrary, Congress passed the TPS statute to standardize the then ad hoc temporary protection system; in Judge Reyes’ words, "to replace executive whim with statutory predictability.” The administration also argued that the harms to Haitian TPS holders were “speculative” if they are forced to return to Haiti. Because the State Department presently warns, “Do not travel to Haiti for any reason,” the administration asserts that harm is “speculative” only because DHS “might not” remove them. However, according to Judge Reyes, this argument fails to take Secretary Noem at her word: “We don’t want them. Not one.” The public interest also favors the injunction, in the opinion of Judge Reyes. Secretary Noem complains of the strains that unlawful immigrants place on our immigration-enforcement system. Noem’s answer is to turn 352,959 lawful TPS Haitian immigrants into unlawful immigrants overnight. Noem complains of strains to our economy; her answer is to turn employed lawful immigrants who contribute billions in taxes into the legally unemployable. Noem complains of strains to our health care system. Noem’s answer is to turn the insured into the uninsured. “This approach is many things – but the public interest is not one of them,” according to Judge Reyes. The opinion of Judge Reyes concludes: “Kristi Noem has a First Amendment right to call immigrants killers, leeches, entitlement junkies, and any other inapt name she wants. Secretary Noem, however, is constrained by both our Constitution and the law to apply faithfully the facts to the law in implementing the TPS program. The record to-date shows she has yet to do that. The administration has already appealed. 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 Office of the Governor February 16, 2026
Gov. Wes Moore signed legislation on February 17, 2026, to prohibit State and local jurisdictions from deputizing officers for federal civil immigration enforcement activity. The law, created under SB 245/HB 444 , is effective immediately. “In Maryland, we defend Constitutional rights and Constitutional policing — and we will not allow untrained, unqualified, and unaccountable ICE agents to deputize our law enforcement officers,” Moore said. “This bill draws a clear line: we will continue to work with federal partners to hold violent offenders accountable, but we refuse to blur the lines between state and federal authority in ways that undermine the trust between law enforcement and the communities they serve. Maryland is a community of immigrants, and that's one of our greatest strengths because this country is incomplete without each and every one of us.” “As an immigrant, this bill is deeply personal to me,” said Lt. Gov. Aruna Miller. “Immigrants make Maryland stronger every day, and our communities are safer when everyone feels protected and valued. This legislation ensures that our law enforcement resources remain focused on keeping Marylanders safe, not on actions that create fear in our neighborhoods. I thank the bill sponsors and Governor Moore for their leadership in ensuring Maryland remains a place where dignity and opportunity go hand in hand.” U.S. Department of Homeland Security Immigration and Customs Enforcement, also known as ICE, established its 287(g) program to authorize local law enforcement officials to perform federal civil immigration enforcement functions under ICE’s oversight. Under SB 245/HB 444, State and local jurisdictions in Maryland are prohibited from engaging in such agreements. Any local jurisdictions with standing 287(g) agreements must terminate them immediately. The legislation does not: Authorize the release of criminals Impact State policies and practices in response to immigration detainers that are issued by the U.S. Department of Homeland Security Prevent the State or local jurisdictions from continuing to work with the federal government on shared public safety priorities, including the removal of violent criminals who pose a risk to public safety Prevent State or local jurisdictions from continuing to notify ICE about the impending release of an individual of interest from custody or from coordinating the safe transfer of custody within constitutional limits State and local law enforcement will also maintain the ability to work with the federal government on criminal investigations and joint task forces unrelated to civil immigration enforcement. Any individual who is charged with a crime is entitled to due process and, if convicted, must serve their sentence.
By Sarah Boden and Drew Hawkins, Gulf States Newsroom February 16, 2026
And now, the enhanced Affordable Care Act subsidies that many Americans, including farmers, relied on to purchase health insurance are gone, having expired at the end of December.
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