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Auburn and Margaret

In early 1859, Frances Adeline Seward, the wife of abolitionist Republican U.S. Senator William H. Seward, sold Tubman a seven-acre (2.8 ha) farm in Fleming, New York, for $1,200 (equivalent to $43,900 in 2023). The adjacent city of Auburn was a hotbed of antislavery activism, and Tubman took the opportunity to move her parents from Canada back to the U.S. Her farmstead became a haven for Tubman's family and friends. For years, she took in relatives and boarders, offering a safe place for black Americans seeking a better life in the north.

Shortly after acquiring the farm, Tubman went back to Maryland and returned with an eight-year-old light-skinned black girl named Margaret, who Tubman said was her niece. She also indicated the girl's parents were free blacks. According to Margaret's daughter Alice, Margaret later described her childhood home as prosperous and said that she left behind a twin brother. These descriptions conflict with what is known about the families of Tubman's siblings, which created uncertainty among historians about the relationship and Tubman's motivations. Alice called Tubman's actions a "kidnapping", saying, "she had taken the child from a sheltered good home to a place where there was nobody to care for her". After speculating in her 2004 biography of Tubman that Margaret might have been Tubman's own secret daughter, Kate Larson found evidence that Margaret was the daughter of Isaac and Mary Woolford, a free black couple who were neighbors of Tubman's parents in Maryland and who had twins named James and Margaret.

In November 1860, Tubman conducted her last rescue mission. Throughout the 1850s, Tubman had been unable to effect the escape of her sister Rachel, and Rachel's two children Ben and Angerine. Upon returning to Dorchester County, Tubman discovered that Rachel had died, and the children could be rescued only if she could pay a bribe of $30 (equivalent to $1,020 in 2023). She did not have the money, so the children remained enslaved. Their fates remain unknown. Never one to waste a trip, Tubman gathered another group, including the Ennalls family, ready and willing to take the risks of the journey north. It took them weeks to get away safely because of slave catchers forcing them to hide out longer than expected. The weather was unseasonably cold and they had little food. The Ennalls' infant child was quieted with paregoric while slave patrols rode by. They safely reached the home of David and Martha Wright in Auburn on December 28, 1860.