Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (2023)

To discover Frederick Douglass — one of the foremost figures in American history — consider the opening salvo of his bestselling 1845 autobiography.

“I was born in Tuckahoe, near Hillsborough, and about 12 miles from Easton, in Talbot county, Maryland,” he recounts in “Narrative of the Life of Frederick Douglass, an American Slave.”


This book and two others that Douglass subsequently authored vividly recount the people, places and events that shaped his extraordinary journey. Slavery to self-emancipation. Global renown as an abolitionist, orator and statesman. Publisher of The North Star, an antislavery newspaper. Advisor to presidents.

On Thursday, more than 200 years after Frederick Augustus Washington Bailey was born in 1818 on the Eastern Shore, sojourners can explore the landscapes of his youth, his pivotal time in Baltimore and beyond, via heritage sites, walking and self-driving tours, exhibits and more.


While many places associated with Douglass no longer exist, some original sites remain remarkably intact.

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (1)

“People can see and explore where Douglass has been, and follow in his footsteps,” said Maryland Lt. Gov. Boyd Rutherford, who has a vintage photo of Douglass lent from the State Archives in his office. “In the 19th century, he was one of the preeminent leaders of his time. It’s important to continue to talk about him, especially to younger people.”

In July, Gov. Larry Hogan’s Administration announced more than 100 matching grants totaling $5.1 million that were awarded to Maryland nonprofits, local jurisdictions, and other heritage tourism organizations by the Maryland Heritage Areas Authority. Grant funds, officials said, will support heritage tourism projects and activities designed to attract visitors, as well as expand economic development and tourism-related job creation throughout the state.

(Video) The Legacy of Frederick Douglass

The list includes 13 locally designated Maryland Heritage Areas, each of which has a distinct focus that represents a unique aspect of Maryland’s character such as African American or Civil War history. Stories of the Chesapeake, a heritage area encompassing Caroline, Kent, Queen Anne’s and Talbot counties, is among the sites that have Douglass-centric themes.

“He’s an inspiration,” said Kenneth B. Morris, Jr., the great-great-great grandson of Douglass and his first wife of 44 years, Anna Murray Douglass.

The couple had five children: Rosetta, Lewis Henry, Frederick Jr., Charles Remond, and Annie, who died at age 10.

“I am a direct descendant of both Douglass and Booker T. Washington,” said Morris. “Our families were joined through marriage.”

His mother, Nettie Washington Douglass, said she has fond memories of “spending summers at Highland Beach,” the historic African American town on the Chesapeake Bay in Anne Arundel County.


The affluent enclave was founded in 1893 by Douglass’ son Charles Remond Douglass, a retired major who served with the U.S. Colored Troops during the Civil War, and his wife, Laura, in response to discrimination. The Frederick Douglass Museum and Cultural Center is housed at Highland Beach in “Twin Oaks”— the summer cottage built in 1895 for Douglass and restored in the 1980s.

These days, Morris said his ancestor’s legacy lives on through “modern day abolition” and the nonprofit Frederick Douglass Family Initiatives, which he cofounded and leads along with his mother. The organization’s efforts center on education, anti-racism programs and combating human trafficking. Morris, 60, also served as a consultant in the new Douglass-inspired musical, “American Prophet,” now playing in Washington, D.C.

Immersion in Douglass’ world, Morris believes, offers a broader lens to absorb his famous speeches and writings that tackled race, democracy, women’s suffrage and human dignity. “Because history lives in each of us,” he said, “we can take these lessons he provided and use them for greatness.”

Here are some places to explore Douglass’ legacy and path to freedom.

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (2)

Location: Faces the Easton Rail Trail at 505 South St., Easton.

(Video) David W. Blight, "Frederick Douglass: Prophet of Freedom"

A colorful mural featuring Frederick Douglass and his beloved wife Anna was unveiled in Easton in fall 2021. It’s situated in The Hill community, which was settled prior to 1770 and is reportedly the oldest free Black enclave in the U.S.


The 27-by-9-foot mural was created by Cambridge artist Michael Rosato, whose “Take My Hand” mural of fellow Marylander Harriet Tubman went viral in 2019.

The Douglass mural chronicles 400 years of African American history. It charts the arrival of the first enslaved Africans in 1619 and depicts Barack Obama, the first Black president, and Kamala Harris, the first Black vice president, on the steps of the White House.

Its imagery includes relatives, many of whom served in the military. Douglass believed military service was a pathway to citizenship for African Americans. He was a recruiter, as was his son Frederick Douglass Jr. Two sons, Lewis and Charles, served with the famous 54th Massachusetts Infantry.

Raised in The Hill community, Tarence Bailey Sr., the five times great-nephew of Douglass, helped spearhead the mural project with broad support.

“People are looking back at my uncle and reading his words again, and they are saying how much of a conscience he was for the nation,” said Bailey, 47, who lives in Trappe. He said his next project involves raising funds to build an African-American cultural center on the Eastern Shore.

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (3)

Location: Talbot County Courthouse, 11 N. Washington Street, Easton.


(Video) Frederick Douglass’ Incredible Legacy | Told by Laurence Fishburne | History at Home

Dedicated in 2011, a bronze and granite statue of Frederick Douglass by sculptor Jay Hall Carpenter stands on the courthouse lawn. Nearby, was the jail where Douglass was held in 1836 after a foiled attempt to escape slavery.

The courthouse, once the site of slave auctions, was where Douglass spoke during a triumphant return visit home in 1878 to deliver an address. On that trip, he revisited the place of his birth — 12 miles east of Easton, in the region called Tuckahoe, and collected soil from the land.

Location: 13211 Lewistown Road, Queen Anne,

This once undeveloped park near the town of Queen Anne now honors Douglass. Like many formerly enslaved individuals, he never knew his exact birthday but chose Feb. 14. A groundbreaking ceremony was that date in 2018 for his 200th commemorative anniversary.

Location: 26 Dover S., Easton.

This boutique bookstore offers some 10,000 titles, including books about Frederick Douglass. Additionally, there’s custom art on the walls by award-winning artist Penelope Gottlieb. One striking image places Douglass among books, flora and Eastern Shore waterfowl.


Nearby is The Wardroom, once a mid-19th century inn. Douglass actually stayed at this property as a free man while visiting Easton. Restored by Bluepoint Hospitality, the main level is an elegant gastronomic shop, and guests who wish to dine in can sample gourmet fare, an extensive wine cellar and tasting room.

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (4)

Locations: Fells Point, Canton

Baltimore played an outsized role in Douglass’ development and life. Around age eight, his “master” presented him as a “gift” to a relative in Baltimore to serve as a companion to their young son, according to the Pulitzer Prize-winning 2018 biography, “Frederick Douglass: Prophet of Freedom,” by David W. Blight.

Douglass lived in the bustling port community of Fells Point. He learned to read, and purchased his first book, “The Columbian Orator,” which helped hone his oratorical talents.

In 1831, he was sent back to St. Michaels, according to a historical account on the Maryland Office of Tourism’s website. There, the 15-year-old founded a Sunday school and secretly taught others to read. It resulted in him being sent to live under a “slave breaker” who often whipped Douglass. However, he would not be broken and fought back.

(Video) Frederick Douglass: Prophet of Freedom

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (5)

Weekend Watch


Plan your weekend with our picks for the best events, restaurant and movie reviews, TV shows and more. Delivered every Thursday.

Later, an attempted escape from a farm on the Eastern Shore resulted in an arrest. At age 18, he was sent back to Baltimore where he developed a trade caulking ships.


There, he met Anna Murray, born free in Denton on the Eastern Shore. Anna was a seamstress and cook.

Path to freedom: Exploring the landscapes and legacy of Frederick Douglass from the Eastern Shore to Baltimore (6)

“My life began on the third of September 1838,” Douglass wrote. “On the morning of the fourth of that month, after an anxious and perilous but safe journey, I found myself in the big city of New York, as a free man…”

He’d been wearing a sailor’s uniform Anna sewed and funds she’d saved to help him escape by train. Anna followed upon word of his safe arrival. The couple married, taking the new surname Douglass. They settled in New Bedford, Massachusetts, and later Rochester, New York.

(Video) David Blight on “Writing the Life of Frederick Douglass”

Later in life, Douglass returned to Baltimore to give an address. Although he abhorred slavery, he felt affection for 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.”

After Anna’s death, Douglass later remarried. He was 77 when he died Feb. 20, 1895, at his Cedar Hill estate in Washington, D.C. His home there is a National Historic Site, however it is closed for renovations until 2023.


What is the legacy of Frederick Douglass mostly about? ›

“Douglass's legacy is the vision to build a better world; a world in which Black people are equal partners and enjoy the same freedoms and opportunities as someone as historically privileged as I am. Douglass's legacy is the legacy of an activist, an advocate, a freedom fighter, and a seeker of justice.

How did Frederick Douglass achieve his freedom? ›

Frederick Douglass escaped from slavery on September 3, 1838, aided by a disguise and job skills he had learned while forced to work in Baltimore's shipyards. Douglass posed as a sailor when he grabbed a train in Baltimore that was headed to Philadelphia.

How did Frederick Douglass contribute to the civil rights movement? ›

He was an abolitionist, human rights and women's rights activist, orator, author, journalist, publisher, and social reformer. Committed to freedom, Douglass dedicated his life to achieving justice for all Americans, in particular African-Americans, women, and minority groups.

What is the significance of the songs to Douglass himself? ›

The songs of the slave represent the sorrows of his heart; and he is relieved by them, only as an aching heart is relieved by its tears.


1. Tracing the Life of Frederick Douglass with MARYLAND CENTER FOR HISTORY AND CULTURE
(Varsity Tutors)
2. The Life and Legacy of Abolitionist Leader Frederick Douglass
(Holyoke Media)
3. Drs. Bieber Lake/Hill/McKenzie/Bacote | The Life and Legacy of Frederick Douglass (09/11/2018)
4. Frederick Douglass—Prophet of Freedom, With David W. Blight (History with David M. Rubenstein)
(New-York Historical Society)
5. Frederick Douglass: The Meaning of July 4th for the Negro
(US National Archives)
6. Frederick Douglass & Wye House
Top Articles
Latest Posts
Article information

Author: Carmelo Roob

Last Updated: 02/18/2023

Views: 6210

Rating: 4.4 / 5 (65 voted)

Reviews: 80% of readers found this page helpful

Author information

Name: Carmelo Roob

Birthday: 1995-01-09

Address: Apt. 915 481 Sipes Cliff, New Gonzalobury, CO 80176

Phone: +6773780339780

Job: Sales Executive

Hobby: Gaming, Jogging, Rugby, Video gaming, Handball, Ice skating, Web surfing

Introduction: My name is Carmelo Roob, I am a modern, handsome, delightful, comfortable, attractive, vast, good person who loves writing and wants to share my knowledge and understanding with you.