Journeying toward Freedom and New Beginnings

On September 17, 1849, Harriet Tubman fled the family that enslaved her with two of her younger brothers, Ben and Henry. Not long into their journey the three of them disagreed on the best way north. Despite Harriet’s protests, they “dragged her with them” back to the familiar woods and fields of the Eastern Shore of Maryland.[1] Not long after Harriet left again, alone, spurred by her desire for freedom and confident in her ability to navigate the landscape. She escaped successfully.

Portrait of an African American woman with a headscarf and cloak, her hands folded in front of her.
Portrait of Harriet Tubman in 1895
When Harriet took her own freedom, Maryland had more “runaway slaves” then any other state in the south. It was a border state, so freedom was relatively close, but people escaping slavery faced beatings, sale, and other punishments if they were caught. Those who assisted in their escape did too. Despite the dangers, a few years later, Harriet returned to the Eastern Shore to try and free her brothers. This time she enlisted the help of a trusted family friend, Jacob Jackson.

Harriet Tubman and Jacob Jackson on the Eastern Shore

The Jacob Jackson home site, part of the Harriet Tubman Underground Railroad National Historical Park, is located on the Eastern Shore of Maryland, near the mouth of Parson’s Creek in Dorchester County. The park, along with the almost 12,000-acre national monument of the same name, memorializes the remarkable legacy of Harriet Tubman through the preservation of the landscape of her youth. Today considered a national hero for her bravery and leadership in the struggle for equal rights for African Americans and women, it was in Dorchester County that Harriet Tubman first experienced the power of collective resistance and learned to read the landscape to facilitate her own escape and that of many others.

On the Jacob Jackson home site, brackish muddy marshes, golden with sedges and grass, spread from Taylors Island Road at the property’s western boundary to thick forests of oak, pine, and sweet gum. Creeks, ditches, and abandoned canals stretch from the ragged edges of the Chesapeake Bay deep into the site. There are no buildings. The wooden houses, barns, and fences that defined these long abandoned fields are gone. Only a sunken road trace, old Martins Lane, now filled with water like a straight narrow river, points toward the land Jacob and Dinah Jackson farmed in the mid-nineteenth century.
A low view across the tops of bright, yellow green grass in an open landscape.
Grasses and sedge at Harriet Tubman Underground Railroad National Historical Park

NPS Photo

In 1853, free Black farmer Jacob Jackson and his wife Dinah purchased slightly more than one-hundred-and-forty acres from James A. Stewart, a white attorney and US Congressman from Cambridge. Stewart’s father, Joseph Stewart, built Parsons Creek Canal (Stewart’s Canal), just south of the Jackson’s farm, in the early decades of the nineteenth century likely through the labor of enslaved and free Black people.

With few roads, waterways such as canals were often the easiest way to move both people and timber. By the time Jacob and Dinah bought their farm, at least some of the land had been timbered, littered with stumps and trees not worth harvesting, but drainage ditches made the clay soil arable. Jacob and Harriet had probably known each other for years, though how many times they worked together to help others to freedom is unknown.

A visitor looks at the twilight sky reflected in the still water of a canal
Stewart's Canal at dusk

NPS Photo

By 1840 approximately forty-year old Jacob was free and living within the community of White Marsh, east of property he would purchase in 1853. His neighbors included Benjamin Ross, Harriet’s father, and the family of John Tubman, Harriet’s future husband. Araminta “Minty” Ross was born in 1822 to enslaved parents Benjamin and Harriet “Rit” Ross. Minty Ross took the name Harriet Tubman after her marriage to John Tubman in 1844. Following her own flight to freedom in 1849, Harriet returned to the Eastern Shore approximately thirteen times, helping more than seventy people escape slavery and journey to freedom in the north.

The community of White Marsh may have developed along a logging track, later White Marsh Road, during the construction of the Parsons Creek Canal south of Madison, then known as Tobacco Stick. Many of the earliest free Black residents of White Marsh may have been manumitted in a wave of manumissions that occurred in 1790 and 1791 in Dorchester County. During the early nineteenth-century when White Marsh was fairly isolated from maintained county roads, it became a center of African American community, both free and enslaved. Within this community, linked by waterways to Baltimore and beyond, many of Harriet Tubman’s former neighbors, family, and friends formed a network of resistance to an institutionalized system of slavery and discrimination.
A channel of water divides a marshy area of low grass and thin trees
View toward the Jacob Jackson home site

NPS Photo

When Jacob helped Harriet to free her brothers from slavery, he was a free, literate Black farmer already under suspicion for assisting enslaved people to take their own freedom. At the time, he lived with his wife Dinah and two girls, Sarah and Rose Jackson, likely their daughters. He and Dinah also took in, or hired through apprenticeship, free young Black people who had little means of supporting themselves.

In late 1854, while Harriet was living in the north, she learned that Eliza Brodess was planning to sell her enslaved brothers Robert, Ben, and Henry Ross after Christmas. With the assistance of a literate friend, Harriet wrote a letter to Jacob to share her escape plans. She began her message with “indifferent matters,” then asked Jacob to “read my letter to the old folks, and give my love to them, and to tell my brothers to be always watching unto prayer, and when the good old ship of Zion comes along, to be ready to step aboard.” The letter was signed “William Henry Jackson.” William grew up around White Marsh and Parson’s Creek and according to Tubman biographer, Sarah Bradford, he was the adopted son of the Jacksons who had left some years earlier for the north. When men came and delivered Harriett’s letter to Jacob they first refused to let him see it, for they were suspicious. According to Sarah Bradford’s book, Scenes from the Life of Harriet Tubman,

“Jacob was not allowed to have his letters till the self-elected inspectors had had the reading of them, and studied into their secret meaning. They, therefore, got together, wiped their glasses, and got them on, and proceeded to a careful perusal of the mysterious document. What it meant, they could not imagine; William Henry Jackson had no parents or brothers, and the letter was incomprehensible. White genius having exhausted itself, black genius was called in, and Jacob’s letter was at last handed to him. Jacob saw at once what it meant, but tossed it down, saying “Dat letter can’t be meant for me, no how. I can’t made head or tail of it,” and walked off and took immediate measures to let Harriet’s brothers know secretly that she was coming, and that they must be ready to start at a moment’s notice for the North.”[2]

Parson's Creek map of land ownership show names of property owners on land between waterways
This map of Parson's Creek area post dates Jackon's tenure. Jackson's property, near the upper-central section, is labeled J. Brown.

From "1877 Illustrated Atlas for Dorchester and Talbot Counties" (Philadelphia, PA: Lake, Griffing & Stevenson, 1877)

Harriet arrived on the Eastern Shore on Christmas Eve, 1854. With no time to lose, her brothers received her message to head north immediately after dark to their parent’s cabin on Poplars Neck in Caroline County. Eventually, Harriet, her three brothers, Henry, Robert and Ben, Ben’s fiancé Jane, and two other enslaved men gathered in a fodder house, a small wooden structure used for storing corn, near Ben and Rit Ross’s cabin. Harriet then led the group more than one hundred miles, either northeast along the Choptank River or east through Federalsburg to Philadelphia and freedom.

These men and women who escaped slavery in the marshes and woods of Dorchester County took new names and began new lives in Ontario, Canada and upstate New York. Jacob and Dinah Jackson stayed and continued to farm their property near White Marsh. Jacob passed away in 1864, the year all enslaved people in Maryland gained their freedom. Research into the lives of Jacob and Dinah Jackson, and that of their neighbors, is ongoing.

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3 minutes, 40 seconds

This video celebrates Harriet Tubman through a visit to the Maryland landscape of her youth and invites you to learn more about Tubman's remarkable legacy as iconic conductor of the Underground Railroad.

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[1] Sarah H. Bradford, Scenes from the Life of Harriet Tubman, (Auburn, New York: W.J. Moses, 1869), 16, as quoted by Kate Clifford Larson in Harriet Tubman, Portrait of an American Hero: Bound for the Promised Land, (Ballantine Books: New York, New York 2008), 79. Larson’s book provides a fascinating and well-researched account of Harriet Tubman’s life in both Dorchester County and New York State, including descriptions of the escape of Harriet and her brothers from slavery.

[2] Bradford, 58.

This article was written by Jennifer Hanna, licensed landscape architect with the Olmsted Center for Landscape Preservation. The Cultural Landscapes Inventory and the Cultural Landscape Report for the Jacob Jackson Home Site are forthcoming.

Harriet Tubman Underground Railroad National Historical Park

Last updated: March 25, 2022