Enslavement in Southampton County, Virginia, the first installment of the trilogy, takes place in 1864, near the end of the American Civil War, on the slave-holding Jacob Williams' middle-class family farm. During the Southampton Insurrection, the farm came under attack by Nat Turner and his insurgents, an event that haunts Jacob. Before the Civil War began, Parson started discussing human rights and the political implications of abolishing slavery with his two brothers. In December 1864, he planned to liberate himself by running away from Jacob Williams' farm and following an eastward path along the Seaboard and Roanoke Railroad to reach Norfolk, Virginia, which was a Union-occupied city.

After darkness on December 3, 1864, the brothers started Parson's escape plan east toward Fort Norfolk. The brothers ran individually through the stacks of peanuts in the field and into the forest, coming upon an abandoned Worrell shanty from the era of the Nat Turner insurrection. They seized provisions, carpentry tools, network maps, and other equipment, and quickly changed clothes, assuming aliases, before continuing their trip east to Norfolk. Near the demarcation of Southampton and the Union line in Suffolk, a two-man Fugitive Patrol seized and interrogated them. They performed a rouse, overpowered the patrol, and escaped, heading east to Norfolk. After several more encounters along the way, Union pickets and recruiters from the 1st Cavalry Regiment, United States Colored Troops, stopped the three men near or at Camp Bower's Hill. Upon reaching Norfolk and in the hands of Union troops, Parson had liberated himself from bondage. Next, they enlisted in the Union Army and steamed across the Chesapeake Bay to Fort Monroe for basic training at Fort Hamilton, Virginia.