Harriet Shephard was likely born in the late 1820s or early 1830s in or around Chestertown, in Kent County, on the Eastern Shore of Maryland. Few details are known about Harriet's life prior to her escape from slavery in October 1855. By then, she was married (her husband's name is unknown) and had five children: Anna Maria, Edwin, Eliza Jane, Mary Ann, and John Henry. It seems likely that Harriet and her children were all owned by George W. T. Perkins of Chestertown. According to the Kent County Slave Statistics, he owned many slaves, including a Mary Ann, a John, an Edwin, an Anna Maria, and several women named Harriet. Furthermore, the 1860 Federal Census indicates that five of Perkins' slaves were by then "fugitives from the state." Using the estimated ages listed in the Kent County Slave Statistics, which provide a "Record of Slaves in Kent County, at the Time of the Adoption of the Constitution in 1864," we can guess that her children ranged in age from "infant" to approximately 12 years old.
It was no surprise that Harriet planned to escape from slavery in the fall of 1855. Her region had been in tumult that year. Around Easter 1855, panic surged among the whites of nearby Talbot and Dorchester counties as rumor of an imminent slave revolt circulated. No such revolt occurred, but by the fall of 1855, Chestertown's slaves seemed almost to flee at will. In September 1855, ten slaves departed with three horses and two carriages. On October 20, seven more escaped. On October 26, eleven more fled, taking with them four horses and two carriages. This last group consisted of Harriet Shephard, her five children, her aunt and uncle, William Thomas Freeman, Thomas Jervis Gooseberry, and an unnamed young man.
While lone mothers did occasionally escape with one or two children, fleeing with children, especially very young ones, was always risky. Harriet's attempt to flee with five children who "were young, and unable to walk" represented an extraordinary hazard. Harriet and her traveling companions found horses and carriages to carry everyone. They left on the night of October 26, 1855, and moved rapidly to Wilmington, Delaware (about forty-five miles away), where the famed antislavery conductor Thomas Garrett lived.
Although William Still wrote that "it is not likely that they knew much about the roads" to Wilmington and beyond, he was probably incorrect. Hundreds of enslaved individuals had fled the region in the 1850s alone, and knowledge of the best roads to follow and agents to seek circulated covertly among the enslaved and free blacks. Indeed, Grace Anna Lewis, who assisted Harriet and her group on October 28, wrote to Still that a local "colored woman . . . knew of their intended flight and of their intention of passing through Wilmington and leaving their horses and carriages there." This individual may well have been Harriet Tillison, a free black woman who had roamed for years between Cecil and Kent counties visiting free blacks and slaves. Tillison was respected for "her wonderful powers of conjuration and fortune-telling." Kent slaveholders, however, had long suspected her of assisting the numerous runaways from the county; "her advent in the county had been followed by the escape of slaves, on more than one occasion," they complained. In summer 1858 officials arrested Tillison for "preaching and circulating pamphlets of an incendiary character."
Shephard also may have been assisted or encouraged by James Bowers, an antislavery Kent County Quaker and farmer whom county slaveholders had long accused of assisting runaways. While Bowers had a number of non-slaveholding white supporters in the county, those allies were unable to prevent Chestertown slaveholders from tarring and feathering Bowers and running him out of the county in late June 1858, about the same time they assailed Tillison.1
On the road to Wilmington, Shephard and the ten others in her group may also have been assisted by George Wilmer, an enslaved man from the Eastern Shore whom Garrett credited in 1855 with having "passed some twenty-five [fugitives] within four months."
Shephard's escape party arrived at Garrett's house in Wilmington the morning of October 27. Such a large group of fugitives could not remain long at any station. Garrett, recognizing their peril, had them leave the horses and carriages hitched in the street in Wilmington and directed them to Quakers just over the Pennsylvania line at Kennett Square. By evening, the group reached the Longwood meetinghouse, where men were building carriage sheds and women were holding a "Fair Circle" to prepare for Philadelphia's annual antislavery fundraiser. After passing a few hours at the meetinghouse, the group was taken to the home of Eusebius Barnard and his wife, Sarah March Barnard, in Pocopson. By the afternoon of the 27th, slavecatchers in pursuit of the Shephard group had already arrived in Wilmington and recovered the horses and carriages. They kept watch on Garrett's house throughout the night.
After providing the fugitives with food and a place to sleep for a few hours, the Barnards instructed their son Eusebius R. Barnard to escort the group to Downington, Pennsylvania, taking some by carriage to the home of Zebulon Thomas and directing the remainder to proceed on foot to the home of Dr. J. K. Eshleman. Eusebius R. Barnard and the fugitives departed from Pocopson in the wee hours of the morning of the 28th. Thomas, in turn, advised Barnard not to leave the fugitives with him but to proceed directly to the home of John Vickers in Lionville. Meanwhile, rather than walking to Eshleman's residence, the group on foot simply followed the carriage to the home of Thomas, too. Thomas and "his colored men" helped Barnard bring everyone to Vickers.
From there, the fugitives were shepherded to the house of Grace Anna Lewis and her sisters, near Kimberton, arriving there by evening. At the Lewis house, it was decided that it would be safest for the group to divide. Harriet and her children remained a little longer with Mrs. Lewis, while Harriet's aunt and uncle and the three young men were forwarded to E. F. Pennypacker and Lewis Peart in Phoenixville. Three from this party were next sent to Norristown and, almost a month later, two of them—teenagers Thomas Jervis Gooseberry and William Thomas Freeman—were forwarded through Philadelphia.
The rest of the Shephards' story can only be speculated. William Still records the arrival of Harriet Shephard and her five children on November 8, 1855, but his accounts for the care, lodging, and transportation of the Shephard family lists only Anna Maria, Eliza Jane, and Edwin. His notes suggest that those three were sent on to New York City, where Sydney Howard Gay, the head of the Vigilance Committee there, would likely have forwarded them to Syracuse or Rochester in upstate New York and on to Rev. Hiram Wilson in St. Catharines, Canada West. What became of Harriet, her son John Henry, and her daughter Mary Ann is unclear, though we can surmise that they aimed for the same destinations. Still may have referred to them using aliases in his records: a "Mary Smith and her two children" are mentioned in the accounts one day after Anna Maria, Eliza Jane, and Edwin Shephard appear. Or, perhaps these three never stopped in Philadelphia at all, but were sent onward directly from Kimberton.
A letter from Grace Anna Lewis to William Still implies that Harriet and her children may have been forwarded to John Jones, the lead agent in Elmira, New York, and himself a former slave from Loudoun County, Virginia. If they ever reached Jones, he likely would have sent them to Buffalo and Niagara Falls. On the Canadian side, his colleague Rev. Hiram Wilson would have met the Shephards and escorted them to St. Catharines.
Brackett, Jeffrey R. The Negro in Maryland: A Study of the Institution of Slavery. Baltimore: Johns Hopkins University Press, 1889.
Maryland State Archives. "Harriet Shepherd (b. ? – d. ?)." Archives of Maryland (Biographical Series). http://msa.maryland.gov/megafile/msa/speccol/sc5400/sc5496/051300/051333/html/51333bio.html (accessed October 21, 2013).
Preston, Dickson J. Talbot County: A History. Centreville, MD: Tidewater Publishers, 1983.
"Runaway Slaves." Baltimore Sun. November 2, 1855.
Sernett, Milton. North Star Country: Upstate New York and the Crusade for African American Freedom. Syracuse: Syracuse University Press, 2002.
Smedley, R. C. History of the Underground Railroad in Chester and the Neighboring Counties of Pennsylvania. Lancaster, PA: Printed at the Office of The Journal, 1883.
Switala, William J. Underground Railroad in Pennsylvania. Mechanicsburg, PA: Stackpole Books, 2001.