Following the success of Stowe's novel, Henson issued an expanded version of his memoir in 1858, Truth Stranger Than Fiction. Father Henson's Story of His Own Life (published Boston: John P. Jewett & Company, 1858). Interest in his life continued, and nearly two decades later, his life story was updated and published as Uncle Tom's Story of His Life: An Autobiography of the Rev. Josiah Henson (1876).
He tried to buy his freedom by giving his master $350 which he had saved up, and a note promising a further $100. Originally Henson only needed to pay the extra $100 by note, Mr. Riley however, added an extra zero to the paper and changed the fee to $1000. Cheated of his money, Henson returned to Kentucky and then escaped to Kent County, U.C., in 1830, after learning he might be sold again. There he founded a settlement and laborer's school for other fugitive slaves at Dawn, Canada West. Henson crossed into Upper Canada via the Niagara River, with his wife Nancy and their four children. Ontario had become a refuge for slaves from the United States after 1793, when Lieutenant-Governor John Graves Simcoe passed "An Act to prevent further introduction of Slaves, and to limit the Term of Contracts for Servitude within this Province". The legislation did not immediately end slavery in the colony, but it did prevent the importation of slaves, meaning that any U.S. slave who set foot in what would eventually become Ontario, was free. By the time Henson arrived, others had already made Ontario home, including Black Loyalists from the American Revolution, and refugees from the War of 1812.
Henson first worked farms near Fort Erie, then Waterloo, moving with friends to Colchester by 1834 to set up a Black settlement on rented land. Through contacts and financial assistance there, he was able to purchase 200 acres (0.81 km2) in Dawn Township, in next-door Kent County, to realize his vision of a self-sufficient community. The Dawn Settlement eventually prospered, reaching a population of 500 at its height, and exporting black walnut lumber to the United States and Britain. Henson purchased an additional 200 acres (0.81 km2) next to the Settlement, where his family lived. Henson also became an active Methodist preacher, and spoke as an abolitionist on routes between Tennessee and Ontario. He also served in the Canadian army as a military officer, having led a Black militia unit in the Rebellion of 1837. Though many residents of the Dawn Settlement returned to the United States after slavery was abolished there, Henson and his wife continued to live in Dawn for the rest of their lives. Henson died at the age of 93 in Dresden, on May 5, 1883.
- The Life of Josiah Henson, Formerly a Slave, Now an Inhabitant of Canada, as Narrated by Himself (1849)
- Truth Stranger Than Fiction. Father Henson's Story of His Own Life (1858)
- Uncle Tom's Story of His Life: An Autobiography of the Rev. Josiah Henson (1876)