On February 21, 1844, John Leeds Kerr died, leaving a will that stipulated that his property should be sold and the proceeds divided among his heirs. While Adams never reported exactly what prompted her escape from slavery, this impending sale may have been the cause, for in August of that same year, when she met Douglass, she was living in West Chester, Pennsylvania. Unlike Douglass, however, Adams never revealed the details of her escape.
West Chester, with its large population of sympathetic Quakers, one stopping point along a route taken by fugitives from Maryland’s Eastern Shore, and Adams’s presence there provides a clue as to how she may have arrived. The fugitive would leave Talbot or its surrounding counties, travel northeast to Delaware, making her way up to the friends of Thomas Garrett in Wilmington. From there, she would gain passage to Philadelphia, then eastward toward David Ruggles’s helpers in New York or west toward the Quakers in West Chester and points further on. Harriet Tubman, from Dorchester County to the south of Talbot County, followed this route herself. Moreover, the seasonal timing for Bailey's departure would be correct, since spring and late summer tended to see a rise in the number of advertisements for escaped slaves.
All that Adams did reveal about her flight was that a black man assisted her and that she went with another woman. Again, she never identified these people, but strong candidates for their roles were John Bennet Adams, his wife Maria Anna (or Anna Maria), and their two children, James and Elizabeth. Both John and Maria were born in Easton, Maryland, in 1825. John Bennet Adams, a free black man, appears in the 1840 U.S. Census fourteen spaces below John Leeds Kerr. By 1850, he was working as a barber in Springfield, Massachusetts -- by then the home of Harriet and Perry Adams -- where he lived with Maria, James (born c. 1842), Elizabeth (born c. 1838), and a 24 year old black man, William Adams. Maria’s obituary included the information that she had been “born in slavery in Maryland” on perhaps dubious date of “July 4, 1817” and that she had escaped with her two children. The paper also reported that, on her 96th birthday, she recalled her life in slavery and “remembered Senator ‘Ben’ Tillman, who was then a small boy and who was distantly related to the family where she lived.” This last bit of information cannot be true since Benjamin “Pitchfork” Tillman was born in South Carolina after Maria Adams made her escape. Yet, it is a telling phonetic mistake since the Tilghman family -- pronounced the same as Tillman – not only populated Talbot county, but also included a member who married into the Kerr family household in Easton.