The Underground Railroad

violence, physical abuse, emotional abuse, and death.

Gather initial thoughts and broad opinions about the book.

1. Whitehead transforms the metaphorical Underground Railroad into a literal subterranean railway system. Do you think this creative choice enhances or detracts from the historical weight of the actual Underground Railroad?

2. Throughout the novel, Cora encounters different forms of racism and oppression as she moves through various states. Which state’s particular brand of racial subjugation did you find most disturbing or thought-provoking, and why?

3. Colson Whitehead uses grapic detail to portray the violence and trauma of enslavement. How does his approach compare to other novels addressing similar themes, such as his own Pulitzer Prize-winning work The Nickel Boys?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Cora demonstrates extraordinary resilience throughout her journey, maintaining her sense of self despite horrific circumstances. Have you encountered moments in your own life during which you needed to draw on inner resilience? What strategies helped you persevere?

2. The garden plot that Cora inherits from her grandmother Ajarry becomes a powerful symbol of identity and resistance. What possessions or spaces in your life have symbolic importance beyond their material value?

3. Throughout the novel, various characters must make difficult moral choices under extreme circumstances. Which character’s decisions resonated with you most, and have you ever faced situations during which your moral compass was similarly tested?

4. Cora’s relationship with her mother is complicated by abandonment and resentment, yet we later learn the tragic circumstances of Mabel’s disappearance. Have you experienced family bonds that have persisted despite separation or misunderstanding?

5. The Valentine farm represents a brief glimpse of what a supportive community could look like for formerly enslaved people. What elements of community have provided you with feelings of belonging or sanctuary?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. Whitehead portrays various forms of white supremacy throughout the novel, from plantation slavery to the medical experimentation in South Carolina. What parallels do you see between these historical manifestations and contemporary forms of racial inequality?

2. The fictional South Carolina program of “uplift” masks a eugenics program targeting Black people. How does this portrayal connect to actual historical examples of medical experimentation on marginalized populations (as explored in works like Harriet A. Washington’s Medical Apartheid), and what responsibilities do institutions have in acknowledging these histories?

3. In North Carolina, white citizens entertain themselves with and come together through public violence against Black people. What does the novel’s depiction of spectacle lynchings suggest about the social and cultural function of racist violence?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does Whitehead’s use of different character vignettes (such as the chapters on Ridgeway, Ethel, and Mabel) contribute to the novel’s exploration of America’s racial history? What perspectives do these interludes add to the central narrative?

2. The Underground Railroad is both a literal plot device and a powerful metaphor. How does this enhance the novel’s themes of escape, progress, and American identity?

3. Several characters in the novel, including Ridgeway, Mingo, and even Homer, participate in systems that oppress their own people or others. How does Whitehead use these characters to complicate simple narratives about good and evil?

4. The novel’s final chapter leaves Cora’s ultimate fate ambiguous. What is the effect of this open-ended conclusion, and what might Whitehead be suggesting about the journey toward freedom for Black Americans?

5. Whitehead frequently disrupts chronological time through flashbacks, vignettes, and chapters that reveal information out of sequence. How does this narrative technique reflect the experiences of enslaved people and their descendants?

6. Throughout the novel, Whitehead incorporates historical documents such as capture notices. How do these authentic-seeming texts interact with the fictional narrative, and what effect do they have on the reader’s understanding of the story’s historical context?

Encourage imaginative and creative connections to the book.

1. The novel portrays America’s different states’ distinct approaches to racist control. What would Whitehead’s fictionalized version of your own state or region reveal about its racial history?

2. The supporting characters in the novel each have their own untold stories. Write or outline a brief narrative from the perspective of a minor character, revealing how they understand their place in this complex world.

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