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The Underground Railroad Teacher’s Guide

By Colson Whitehead

The Underground Railroad by Colson Whitehead



Note to Teachers
The Underground Railroad by Colson Whitehead introduces Cora, a young African American woman who journeys to freedom from the antebellum South on a fantastically imagined physical—rather than metaphorical—railroad. Told in episodes, the places and people Cora encounters provide her and the reader with profound revelations of the impact of enslavement. Given the enduring struggle of this country to grapple with the treatment of Africans in America, The Underground Railroad is a critical text for opening up conversations about the lasting legacies of slavery. Through Cora, the reader is reminded of the necessity of hope, of rebellion, and of freedom, making The Underground Railroad an indispensable addition to any classroom.
To begin, teachers will benefit from preparing themselves, and their students, to have difficult conversations about race, racism, and white supremacy. An understanding of the slave trade, slavery, and how it functioned in the United States is essential to be able to make sense of the number of Africans who were enslaved and the historical legacy of enslavement through Reconstruction, the civil rights movement, up to today. Additionally, background knowledge of how lynching and other forms of racial terror were used as enforcement and of slave narratives and the rich literary history of African Americans deepens the reading experiences.
Most important, incorporating The Underground Railroad allows readers to bear witness to a counter-narrative of slavery that is often not discussed. As Cora charts her own path The Underground Railroad reminds us that her story can be a basis for broader discussions of race, gender, and many other important themes.
Supporting the national Common Core State Standards (CCSS) in reading literature for high school curriculums, The Underground Railroad is an appropriate selection for grades eleven and twelve in language arts or U.S. history classes. At the college level, the book is appropriate for composition and literature classes, race studies, gender studies, and is also ideal for first-year/common reading programs.
In the following “Examining Content Using Common Core State Standards” section of this guide, the prompts provide for a critical analysis of The Underground Railroad using the CCSS for Reading Literature and History/Social Studies for grades eleven and twelve and are organized according to the standard they primarily support. In addition, at the end of each standard and the corresponding prompts, a classroom activity is provided that will strengthen analysis of the text.
For a complete listing of the Standards, go to:
Trigger warnings: The text contains numerous scenes of violence (sexual and physical). Teachers might choose to provide advance notice for readers as appropriate. Teachers should not, however, avoid exposing students to these moments; rather, helping students navigate them through discussion and critical analysis will deepen their knowledge of the impact of enslavement as experienced by so many. The pre-reading activities offer some ideas about how to create a community that encourages critical conversations.
Classroom Activity
List all the ways that Cora resists the dehumanization of enslavement. Consider her ownership of the plot of land, her friendships with the Hob women, her insistence on confronting danger, her pursuit of literacy, and other examples. Then conduct a Socratic seminar to evaluate in which ways she is an “insurrection of one” (172) and decide why her resistance makes her such a threat to the system of white supremacy.

Key Ideas and Details 
Analyze the impact of the author’s choices regarding how to develop and relate elements of a story or drama (e.g., where a story is set, how the action is ordered, how the characters are introduced and developed).
In South Carolina, celebrations among the slaves are still engineered by whites, but free people are able to gather and spend time together at will. Compare these free gatherings to those on the Randall plantation for Jockey’s birthday, and later at the Valentine farm. What do these gatherings suggest about community, kinship, and joy? What is significant about these gatherings at the Valentine farm?
How is South Carolina another form of enslavement? What similarities does South Carolina share with Randall? In what ways is South Carolina worse than Randall?
Cora spends her time in North Carolina reading in the attic. Her reading material includes a Bible and almanacs, which “Cora adored . . . for containing the entire world” (183). How does the act of reading, and of literacy, help Cora be free? What might the significance of what she reads suggest about her growing understanding of the world? Think, too, about how the Bible and religion are used by Ethel and Ridgeway to justify slavery: “If God had not meant for Africans to be enslaved, they wouldn’t be in chains” (195), and about Cora’s observation: “Slavery is a sin when whites were put to the yoke, but not the African” (182).
Ridgeway explains his position as follows: “I’m a notion of order. The slave that disappears–it’s a notion, too. Of hope. Undoing what I do so that a slave the next plantation over gets an idea that it can run, too. If we allow that, we accept the flaw in the imperative. And I refuse” (223). What is the “flaw in the imperative,” and why is it important for Ridgeway and the broader institution of enslavement that relies on Black bodies, that the flaw is exterminated? Why is the hope of freedom so dangerous?
Compare Mingo to Lander. What does each man believe and how do those beliefs impact the future of Valentine farm? How are these two men similar to Booker T. Washington and W. E. B. Du Bois?
Cora muses about the Underground Railroad, “Who are you after you finish something this magnificent–in constructing it you have also journeyed through it, to the other side” (303–304). Critique the significance of how each person who worked on the Railroad—from station agents to conductors—were affected by their work. How is each person a reflection of what awaits Cora in the next part of their journey? In what ways, also, do these people understand resistance, agency, and responsibility?
Classroom Activity
The concept of “freedom for literacy and literacy freedom” extends throughout African American history. The ability to read and to be literate allowed one to have a powerful tool of understanding the world and for freeing others. Discuss the culmination of Cora’s literacy journey at the Valentine library. Consider the significance of the Valentine library, “the biggest collection of negro literature this side of Chicago” (273). What is important about the contents of the library and Cora’s experience there? How does Cora’s experience articulate freedom for literacy and literacy for freedom?
Craft and Structure
Analyze how an author’s choices concerning how to structure specific parts of a text (e.g., the choice of where to begin or end a story, the choice to provide a comedic or tragic resolution) contribute to its overall structure and meaning as well as its aesthetic impact.
Our first introduction to Cora is through her grandmother, Ajarry, a woman who never left the plantation on which she was enslaved, seeing escape as impossible. How does Ajarry help to create an example for Mabel and for Cora, in particular? Explain why the narrative begins here.
Colson Whitehead has compared the episodic structure of The Underground Railroad to Jonathan Swift’s Gulliver’s Travels. Each place Cora lands is a different experience and according to Whitehead, “the book is rebooting every time the person goes to a different state.” How does this structure help to develop the narrative and its themes?
Lumbly, a station agent, says to Cora: “If you want to see what this nation is all about, I always say, you have to ride the rails. Look outside as you speed through, and you’ll find the true face of America” (69). How does Lumbly’s assessment frame the next part of Cora’s journey after leaving Georgia?  How does it help the reader understand the novel’s structure?
Cora makes most of her journey alone. While she has companionship at points along her travels, she ultimately is by herself: “She was a stray after all. . . . Somewhere, years ago, she had stepped off the path of life and could no longer find her way back to the family of people” (145). Why must she travel alone? Also, how do her travels help her think about the omnipresent danger of sexual violence for Black women and a broader lack of safety for enslaved women?
North Carolina is a place constructed from fear. Evaluate the Friday Festivals and the night riders. What purpose does each serve? How do these events articulate fears of black rebellion?
Caesar was betrayed by his owner who promised to free him upon her death. Instead, he and his family were sold and separated. Upon arrival at the Randall plantation, he hides a book and reads it at night. The book is Gulliver’s Travels. Analyze the importance of literacy for Caesar, particularly in relation to the line “But if he didn’t read, he was a slave” (235), and “Now a page here and there, in the golden afternoon light, sustained him.” What similarities do Cora and Caesar share? How does Caesar’s thirst for literacy sustain the broader theme of literacy for freedom?
Oxford Bibliographies defines Maroons as “people who escaped slavery to create independent groups and communities on the outskirts of slave societies.” Consider the creation of the Valentine farm as a Maroon society. Who founded it? Who lived there? Why was this both a “community laboring for something lovely and rare” and a threat to others (i.e., the people in the neighboring town, slave catchers, etc.)?
Even after losing his livelihood, Sam continued his Underground Railroad work. What is the message about risk and reward? What does Sam’s work suggest about his belief in the mission and about the responsibility of those who were agents and conductors for the Railroad? Out of all the agents who Cora encountered, why is Sam the one who returns? Evaluate his significance, particularly as related to the time and the location of his return.
Analyze Lander’s response to Mingo on p. 285. Lander counters: “Sometimes a useful delusion is better than a useless truth.” He then lists and explains examples of delusions: “that we can escape slavery,” “Valentine farm,” or “America, too, is a delusion, the grandest one of all.” What does Lander mean? How does delusion function throughout the novel, and why is this moment pivotal for the actions that follow?
Though the inheritance of property was forbidden for the enslaved, Cora’s “mother had left that in her inheritance, at least, a tidy plot to watch over. You’re supposed to pass on something useful to your children” (293). What have Mabel and Ajarry passed on to Cora? What is their legacy realized in Cora?

Listen to Whitehead’s interview with Terry Gross on Fresh Air (link in the Resources section) where he discusses his decisions to make the Underground Railroad a literal one and takes creative license with historical events. Explore the significance of making the Underground Railroad an actual railroad.
Classroom Activity
Whitehead included primary sources of actual runaway reward advertisements throughout the novel, including one for Cora as the last announcement on page 298. Using a framing text (i.e., “New Databases Offer Insight into the Lives of Escaped Slaves” from the New York Times), create stations for students to analyze and discuss each advertisement. In what ways do these advertisements demonstrate resourcefulness and resistance? What similarities and differences exist between the actual announcements and Cora’s? Students may write a short response and use it as part of small group discussions.
Integration of Knowledge and Ideas
Integrate and evaluate multiple sources of information presented in diverse formats and media (e.g., visually, quantitatively, as well as in words) in order to address a question or solve a problem.
In the New Yorker article, “The Perilous Lure of the Underground Railroad,” Kathryn Schultz writes: “That story, like so many that we tell about our nation’s past, has a tricky relationship to the truth: not quite wrong, but simplified; not quite a myth, but mythologized.” Discussions of the historical underground railroad often centralize the role of white abolitionists. Why is it important to foreground African Americans’ role in abolition, as, notably, “All the railroad men, from Lumbly to Royal, countered with a variation of ‘Who do you think made it? Who makes everything?’” (257).
The 2003 Slave Memorial Act “authorizes the National Foundation for African American Heritage to establish in the District of Columbia a memorial to slavery to: (1) acknowledge the fundamental injustice, cruelty, brutality, and inhumanity of slavery in the United States and the thirteen American colonies; and (2) honor the nameless and forgotten men, women, and children who have gone unrecognized for their undeniable and weighty U.S. contribution.” There are currently no national monuments that mark the enslavement of Africans in America. Ta-Nehesi Coates has argued for reparations for the descendants of enslaved Africans as restitution. What is the most appropriate way to honor and remember enslavement?
Classroom Activity
Cora is part of a long line of African American females resistant to white supremacy. Create an artistic representation that places Cora within that lineage, drawing on examples from the text to support your thinking, extending the timeline to the present day.
Research to Build and Present Knowledge CCSS.ELA-LITERACY.WHST.11-12.7
Conduct short as well as more sustained research projects to answer a question (including a self-generated question) or solve a problem; narrow or broaden the inquiry when appropriate; synthesize multiple sources on the subject, demonstrating understanding of the subject under investigation.
The Underground Railroad draws on actual historical events to create a compelling narrative. Select one of the episodes and use it as a point of departure for conducting a critical analysis and presenting research about one of the following topics and how it connects to understanding themes in the novel. Consult the Resources section for additional information.
●        Forced sterilization
●        Settler colonialism
●        Lynching
●        African Americans and abolitionism
●        African American slave rebellions
●        Sexual violence and African American women
●        Reparations
●        Literacy practices during and beyond enslavement
●        The role of white women in slavery
●        Maroons and Marronage
●        Racial health disparities
Abolition Seminar. (

Coates, Ta-Nehisi. “The Case for Reparations,” The Atlantic.

“Equal Justice Institute Report on Lynching in America.” (

“Eugenics: Compulsory Sterilization in 50 American States” (

Everyday Feminism, “Here’s What a White Savior Is (And Why It’s the Opposite of Helpful).”

Global Social Theory, “Introduction to Settler Colonialism from Global Social Theory.” (

Kahn, E. “New Databases Offer Insight Into the Lives of Escaped Slaves,” The New York Times.

“Colson Whitehead’s ‘Underground Railroad’ Is a Literal Train to Freedom,” Fresh Air, NPR.

Oxford Bibliographies, “Maroons and Marronage.”

Schulz, Kathryn, “The Perilous Lure of the Underground Railroad,” The New Yorker.

Other Works of Interest
Historically Black Podcast. (, APM Reports & The Washington Post

Octavia Butler

Freedom Over Me, Ashley Bryan (children’s literature)

The Language You Cry In (film), California Newsreel

Between the World and Me, Ta-Nehisi Coates

13th (film), Ava DuVernay

The African Americans: Many Rivers to Cross (film), Henry Louis Gates, Jr.

Strange Fruit: Uncelebrated Narratives from Black History, Joel C. Gill

Roots (film), Alex Haley

The People Could Fly, Virginia Hamilton (children’s literature)

Their Eyes Were Watching God, Zora Neale Hurston

Song of Solomon, Toni Morrison

Young, Gifted and Black: Promoting High Achievement Among African American Students, Theresa Perry

The Immortal Life of Henrietta Lacks, Rebecca Skloot

Smithsonian American Art Museum. Literacy as Freedom,

The Great Debaters (film), Denzel Washington

Freedom in Congo Square, Carol Boston Weatherford & Gregory Christie. (children’s literature)

The Warmth of Other Suns: The Epic Story of America’s Great Migration, Isabel Wilkerson

Help Me to Find My People: The African American Search for Family Lost in Slavery, Heather Andrea Williams

Self-Taught: African American Education in Slavery and Freedom, Heather Andrea Williams

Lynching Project website, Monroe Work.  
About This Guide’s Writer
Dr. Kimberly N. Parker currently teaches English at Cambridge, Rindge and Latin School in Cambridge, MA. She is the past president of the New England Association of Teachers of English and the former Secondary Representative at-Large for the National Council of Teachers of English. Dr. Parker holds a Ph.D. in Curriculum and Instruction from the University of Illinois-Urbana Champaign.


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