Douglass was born in Tuckahoe, which he described in My Bondage and My Freedom as a "singularly unpromising and truly famine stricken district" in Talbot County, Maryland. Many slaveholders didn't bother to record the family histories of enslaved people, and not being able to read, write, or count months made it hard for the people themselves to keep careful records. As such, Douglass never knew his exact birthdate: He estimated it was in February 1817 or 1818 and later chose to celebrate his birthday on Valentine's Day, February 14.

Douglass never knew who his father was, just that he was probably white and was rumored to be Captain Anthony, the slaveholder who had enslaved Douglass' mother. For the first seven or so years of his life, Douglass was raised by his maternal grandparents, Betsey and Isaac Bailey. Although Isaac was free, Betsey was an enslaved woman and was well-respected in the region for her nursing, fishing, and gardening skills, as well as for looking after children whose parents had been sent away.

Douglass' mother Harriet was one such person. She had been "hired out," sent by Anthony to work for another farmer 12 miles away. When possible, she would walk to visit Douglass, but she had to be home in time for roll call in the fields. Douglass only saw her a few times in his life and mostly remembered the way she looked: He wrote in Life and Times that she was tall, dark-skinned, and dignified.

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