With his long hair and a salt-and-pepper beard lending a stately quality to a face that reflects a life of struggle, Frederick Douglass looks every bit the abolitionist, author and human rights advocate. In another life, he could have been a college professor. Instead, he was born into slavery, on a Maryland farm, the son of an unknown white man. Douglass worked the fields until his eighth birthday, when he was sent to caulk ships. His new owner Hugh Auld broke a state law by educating Douglass, which only intensified the desire for escape. On a dark September night, he seized his chance.

On this day, September 3, in 1838, Frederick Douglass made his dramatic escape from slavery—traveling north by train and boat from Baltimore, through Delaware, to Philadelphia. From there Douglass hopped a train to New York, where he arrived the following morning.

A free man in the North, Douglass eventually settled in Bedford, Massachusetts, taking on work at the docks. By the late 1840s, Douglass was secure enough to reveal his status as a former runaway, displaying his ability to read and write as a refutation to those believing slaves were incapable of such intelligence. Douglass eloquently documented his flight from captivity and his new life in his seminal autobiography The Narrative of the Life of Frederick Douglass, an American Slave.