In the eighteenth century, Halifax became a major trade center and port on the south bank of the Roanoke River at the intersection of major roads, and its taverns, print shops, and docks provided information that could determine the success or failure of people escaping slavery. Free blacks and sympathetic whites shared news, communicated secretly, and helped conceal fugitives’ identities and hiding places. Halifax County often had the largest population of enslaved residents in North Carolina, including laborers, skilled tradespeople, craftspeople, gardeners, cooks, ferrymen, and boatmen, and runaways such as Sparrow, Ephraim, Eliza, and Juba used their knowledge of the river to aid their escape. Across the river, a community of antislavery Quakers also offered help, and an 1830 newspaper article reported that they removed more than 600 persons of color from North Carolina. The Roanoke River was crucial to the transportation network of northeastern North Carolina and south central Virginia, carrying planters’ goods downstream to Edenton on the Albemarle Sound, while black boatmen spread information along its banks. The river also helped fugitives avoid slave patrols and hastened their flight to urban areas, swamps, the sounds, open seas, and ultimately northward to freedom.