In this gripping story, Simon and Josiah flee Virginia's turmoil for the promise of freedom in Canada during the Civil War. Their unyielding friendship and deepening faith guide them through treacherous trials and unexpected romances.
Simon, a 24-year-old graduate of the Lutheran seminary in Gettysburg, and 19-year-old Josiah, a slave on a Virginia plantation, embark on a perilous journey north. As they travel, their bond strengthens, with Simon mentoring Josiah, whose growing faith helps him endure numerous hardships, eventually becoming a devout believer.
Simon had been engaged to Emily, a planter's daughter, but her father forces her to end the engagement when Simon refuses to join the Confederate Army. Josiah, a quadroon, is the illegitimate son of the planter and his mulatto housekeeper, a secret known only to them.
To avoid service in the Confederate Army, Simon heads to Canada, with Josiah seeking freedom by his side. Their journey is fraught with danger and challenges, but they also find love. Simon meets Gabrielle, an escaped slave, at a Quaker farm where he recovers after slave hunters attack him and abduct Josiah. Two Indian men rescue Josiah, reuniting him with Simon at the farm, a stop on the Underground Railroad. Later in Ohio, Josiah meets and falls in love with 17-year-old Justine, who is half Wyandotte Indian.
Gabrielle, initially believed to be one of the Quaker family's daughters, is actually an octoroon girl who escaped sexual slavery. She blends into the Quaker family, who invite her to stay. Despite her past, she eventually overcomes her fears and falls in love with Simon, with the support of her adoptive Quaker family. Justine, raised in a loving Christian home, receives wholehearted approval from her family for her relationship with Josiah.
Reaching Chatham, Ontario, Simon and Josiah start a successful cobbling business. However, both are eventually drawn to join the war effort. Simon enlists as a Union chaplain, and after meeting Frederick Douglass, Josiah joins an all-black Massachusetts infantry regiment. In his first battle, Josiah is captured and sold back into slavery in Virginia. He escapes but faces his former captor, the slave hunter, who intends to kill him.