Archives of Maryland
(Biographical Series)

William "Bill" Bailey (b. 1825 - d. ?)
MSA SC 5496-8253
Fled from Slavery, Talbot County, Maryland, 1856


    William Bailey successfully escaped from Talbot County, Maryland, on November 15, 1856, with fellow slaves Josiah "Joe" Bailey and Peter Pennington.  He was owned by John C. Henry, a resident of Easton who often hired out Bailey's services. Henry, along with William R. Hughlett and Turpin Wright, placed a runaway slave advertisement for the group of fugitives, offering a three hundred dollar reward for Bill.1 He and his brother were simply tired of the ill treatment that they received while working at Hughlett's timber business along the Choptank River. Bill had recently received a flogging, which left him with the opinion that "redress there was none, save to escape."2

    Being familiar with Harriet Tubman's clandestine activities in the area, Joe Bailey had asked Ben Ross to alert them of her next arrival.3 With the knowledge and connections of "Moses" the group was able to make it nearly as far as Wilmington, Delaware. However, their zealous owners had beaten them to the important Underground Railroad depot, preventing the men from receiving immediate assistance from Thomas Garrett and other known agents. Even with police and local slave catchers patrolling the area, Garrett's network of accomplices was able to execute a daring plan to extricate the fugitives. He employed a group of black bricklayers to hide the five individuals in their loaded wagon, "singing and shouting" as to ease the potential suspicions of ever present patrollers.4 They were then forwarded to William Still in Philadelphia, where he recorded some of  the details regarding their enslavement in Maryland.5

    Bill and his brother Joe made it all the way to Canada, and were integrated into the fugitive community in St. Catharine's. It was here that the Baileys were recruited by Harriet Tubman to assist John Brown in his ambitious strike against slavery in Virginia.6 Along with Eastern Shore natives Thomas Elliot, Denard Hughes, and Peter Pennington, among others, Tubman had initially organized a legitimate force to support Brown. The Canadian contingent ultimately decided not to join him in the ill-fated 1859 mission.7 However, even their consideration of Brown's plan was evidence of just how fervently Bill Bailey and his fellow fugitives opposed the institution. As of 1861, Bailey was living in Canada West, where the Census recorded him as a laborer.8 Unfortunately, there is little additional documentation to suggest how Bailey adjusted to life in his new home.

Footnotes - 

1. "Two Thousand Six Hundred Dollars Reward" Baltimore Sun, 22 November 1856.

2. William Still . The Underground Railroad:  A Record of Facts, Authentic Narratives, Letters, etc.  (Philadelphia: Porter & Coates, 1872), pp. 272-274

3. University of North Carolina at Chapel Hill Libaries: Documenting the American South.  "Harriet, the Moses of Her People, Bradford, Sarah H."

4. Ibid. 

5. Still, pp. 273-274. 

6. Kate Clifford Larson. Bound for the Promised Land: Harriet Tubman, Portrait of an American Hero. Ballantine Books: New York, NY, 2004, p. 159. 

7. Ibid. 

8. 1861 Canada West Census, Wentworth County, p. 35.

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