Young Douglass reached Havre de Grace, Maryland, in Harford County, in the northeast corner of the state, along the southwest shore of the Susquehanna River, which flowed into the Chesapeake Bay. Although this placed him only some 20 miles (32 km) from the Maryland-Pennsylvania state line, it was easier to continue by rail through Delaware, another slave state. Dressed in a sailor's uniform provided to him by Murray, who also gave him part of her savings to cover his travel costs, he carried identification papers and protection papers that he had obtained from a free black seaman.
Douglass crossed the wide Susquehanna River by the railroad's steam-ferry at Havre de Grace to Perryville on the opposite shore, in Cecil County, then continued by train across the state line to Wilmington, Delaware, a large port at the head of the Delaware Bay.
From there, because the rail line was not yet completed, he went by steamboat along the Delaware River further northeast to the "Quaker City" of Philadelphia, Pennsylvania, an anti-slavery stronghold. He continued to the safe house of noted abolitionist David Ruggles in New York City. His entire journey to freedom took less than 24 hours. Frederick Douglass later wrote of his arrival in New York City: I have often been asked, how I felt when first I found myself on free soil. And my readers may share the same curiosity. There is scarcely anything in my experience about which I could not give a more satisfactory answer. A new world had opened upon me. If life is more than breath, and the 'quick round of blood,' I lived more in one day than in a year of my slave life. It was a time of joyous excitement which words can but tamely describe. In a letter written to a friend soon after reaching New York, I said: 'I felt as one might feel upon escape from a den of hungry lions.' Anguish and grief, like darkness and rain, may be depicted; but gladness and joy, like the rainbow, defy the skill of pen or pencil.
Once Douglass had arrived New York, he sent for Murray to follow him north to New York. She brought with her the necessary basics for them to set up a home. They were married on September 15, 1838, by a black Presbyterian minister, just eleven days after Douglass had reached New York. Douglass and Anna had five children: Rosetta Douglass, Lewis Henry Douglass, Frederick Douglass Jr., Charles Remond Douglass, and Annie Douglass (died at the age of ten).