The year 1858 was a monumental one in the lives of Ann Maria Jackson and her family. In that year she bravely took destiny into her own hands and escaped from her Maryland slave owner. With her she took seven of her nine children, ranging from 2 up to about 19 years old. Philadelphia abolitionist and Underground Railroad stationmaster William Still helped the family on their way north to Canada. In his book, The Underground Railroad, Still remarked how unusual it was to see a woman with so many young children taking such a risk in making a bid for their freedom.
Mrs. Jackson had been a victim of a terrible tragedy the previous fall. Her two eldest children had been sold away and her husband, a free man named John Jackson who worked as a blacksmith, had gone insane and died in the poor house because of the sale of his two sons. What prompted Ann Maria to gather up her remaining children and try to escape in 1858? She had learned at the last moment that her owner – who also owned all of her children – had made plans to sell her four more children away from her.
Along the way through Delaware, the slave state where she and her family lived, Ann Maria was terrified that they had been betrayed. However, Underground Railroad agents were watching out for them, and the family was picked up by horse-drawn carriage just outside of Wilmington, Delaware. The Jacksons were then transferred to a second carriage and driven across the border into Chester County, Pennsylvania, which was in free territory.
But they were not yet safe. Federal laws allowed slave owners and their agents to chase runaway servants and recapture them, have them tried before a judge in court, and then return them to slavery. So Ann Maria Jackson and her children were transported on to Philadelphia where they met with William Still, Secretary of the Pennsylvania Antislavery Society. After interviewing the family and recording their story, Still quickly sent them on through Pennsylvania and New York State to St. Catharines, Canada West. There, they stayed with abolitionist and UGRR agent Reverend Hiram Wilson, who in turn, sent them on to Toronto.
The Jacksons settled in Toronto, where Mrs. Jackson began working as a washerwoman to support her family. By 1861, they were renting a one-storey frame house at 93 Elizabeth Street, near Osgoode Hall, just north of Queen Street east of University Avenue. Happily, one of Ann Maria’s sons who had been sold away, James Henry, also escaped. He had made his way to the St. Catharines area. James Henry Jackson was reunited with his family in Toronto.
Ann Maria’s children went on to become productive citizens, with one daughter following in her mother’s footsteps as a laundress, two sons becoming barbers, and one a waiter. The final piece to the puzzle was Ann Maria’s reunion with Richard M. Jackson, her other son who had originally been sold away back in Maryland. He went on to become a popular and well-liked barber in Toronto, and owned hairdressing establishments that were frequented by wealthy and prominent Torontonians. The baby of the family, Albert Jackson, would grow up to become the first Black letter carrier in Toronto in 1882. However, he only could take his position after a battle was waged by the community, for his fellow mailmen refused to train him because of racism. Albert Jackson was able to take up his job, retiring in 1918 after 36 years of service.