Several years earlier, in 1835, Henry Bibb made his first escape attempt when he was hired out to Mr. Vires, who lived on a nearby farm in Newcastle, Kentucky. Although he was hoping to reach Canada with great ease, Bibb was captured in less than twenty-four hours, whipped and placed in isolation. However, determined to obtain his freedom, Bibb planned and executed another escape attempt, but the same result took place. He was recaptured rather quickly and whipped once again.
The determination of Bibb to ultimately gain his freedom was temporarily halted when he began to date and subsequently married an enslaved African American woman named Malinda, who resided in a nearby plantation in Oldham, County, Kentucky. Once married, Bibb soon became a father. However, the hardship of being a husband and father whose wife and child was owned by a white man soon reignited Bibb’s aspiration to escape once again. As a result, and with a promise to his wife to return to them after he was completely free, Bibb absconded on Christmas Day in 1837.
When he had reached Cincinnati, Ohio, with the help several local African Americans, Bibb was introduced to a group of abolitionists who helped him travel further north through the Underground Railroad of Cincinnati to Perrysburg, Ohio. Bibb stayed in Perrysburg several months before he eventually headed back to Kentucky to free his wife and child. When he reached them, Bibb developed a plan to help them escape by steamship once that reached the Ohio River. Unfortunately, they failed to reach the rendezvous point on time, and thus Bibb was recaptured by a slave catcher who had been posing as a local abolitionist and subsequently shipped to Louisville, Kentucky to be sold. However, Bibb managed to once again escape from his captor. After his escape, Bibb traveled to central Ohio, but several years later, in 1839, he returned to Kentucky once again to try to free his wife and child. But, again, he was recaptured and shipped to Louisville. But this time his family was shipped with him to keep him from another escape attempt.
Furthermore, several months later, Bibb and his family, along with several hundred enslaved African Americans, were placed on a steamship that left Louisville, bound for Vicksburg, Tennessee and eventually New Orleans, Louisiana. Once in New Orleans, in 1840, Bibb and his family were separated, with his wife and daughter being sold to local gamblers and Bibb being purchased by a local Native American. However, the next year, in 1841, Bibb escaped from the Native American, for good this time, traveled to the Mississippi River, and then secretly climbed aboard a steamboat that was on route to Portsmouth, Ohio.
By the late 1840s, Bibb had come to terms that he would never see (first) his wife and child again. As a result, he remarried in 1848 and over time became an ardent African American abolitionist in several New England and Middle Atlantic states. As an abolitionist, to tell his story to a wider audience, in 1849 Bibb published his autobiography titled Narrative of the Life and Adventures of Henry Bibb, An American Slave. The next year, in 1849, he and his new wife published the first African American newspaper in Canada titled, Voice of the Fugitive.