Perhaps a majority of successful runaways escaped to towns and cities. Even in colonial days these urban areas offered them unique opportunities for autonomy and anonymity. The hiring of enslaved men and women by townspeople, as well as self-hire was common, and by the early 1800s, most Southern cities had hundreds and sometimes thousands of hired bondspeople, making it possible for escapees to blend in.

Resourceful fugitives who made it to urban centers could find ways to conceal their identities, create new ones, perhaps find shelter with relatives -enslaved and free- and possibly lose themselves in growing free black populations. Many who succeeded in hiding their true identities were literate, possessed marketable skills, and could easily pass as free. They knew what whites wanted to hear and could produce a plausible explanation of their backgrounds. Males found work as laborers, carpenters, masons, bricklayers, mechanics, shoemakers, and tradesmen; women were employed as house servants, cooks, maids, and laundresses.

Although escapees still faced the constant danger of being stopped and questioned by the authorities or suspicious citizens, control was less intensive than in the country­side, where black strangers were scrutinized and often arrested. As Baltimore, Washington, D.C., Richmond, Louisville, Nashville, Mobile, New Orleans, and St. Louis grew, it became increasingly difficult for authorities to keep track of the expanding African-American populations.

Residential patterns in these cities impeded the ability of the authorities to check the identities of African-Americans. They lived in alleys behind their owners' town houses, in rundown houses along the rivers and in residential areas and suburbs where they worked as house servants.

There was little racial separation: regular slaves, hired slaves, free persons of color, and runaways lived in close proximity to white artisans and mechanics as well as members of the planter aristocracy. Although detailed statistics do not exist, local police records suggest that there was a continual flow of fugitives into urban areas.

In these cities where runaways might have relatives and friends, there were also free blacks willing to assist and religious institutions that would take them in. In the Upper South cities, many legally free people, who had recently emerged from bondage, sympathized with the fugitives' plight and provided aid and comfort. A free mulatto in Camden, Delaware, Samuel D. Burris, was described as "notorious" for providing protection to fugitives. Despite a previous conviction, an observer reported, "Burris still persists in the nefarious practice of enticing Servants and Slaves away from their Masters."