The Old Jail (1858) of St. Mary’s County, Maryland, is located in Leonardtown, a port accessing the Chesapeake Bay via the Potomac River. Tobacco was a major crop in St. Mary’s until the twentieth century and the first slaves were documented here in 1644. The Old Jail plays a central role in the story of slavery and “Flights to Freedom” in St. Mary’s County and Southern Maryland. It was common for runaways to be held in a public jail until their owner retrieved them or they were sold for cost of care. At least 5 examples of runaway slaves incarcerated in the Old Jail are found in the local newspapers (1858-1864). These examples give insight to themes found throughout the “Flight to Freedom” stories. The stories of the runaways held at the Old Jail exhibit motivating factors of escape. These include fear of being sold after a master’s death, influence of free blacks on enslaved, importance of family, and the advantage of water travel.