Book Club Questions for The Lincoln Highway by Amor Towles

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Book club questions for The Lincoln Highway by Amor Towles takes an in-depth look at this complicated and big novel about the journey to adulthood. There will be spoilers so for more context about the book, check out my spoiler-free review first.

Whew. This was something else, right? It seems people either love or actively dislike this novel but I’m somewhere in the middle. There are elements I enjoyed but others, I was quite perplexed by.

And that climax and ending! I did not see that coming at first. However, the more I thought about it, I can think back where the author did lay the ground work, at least somewhat. But I’m still a bit puzzled by the shift in tone. I have so many thoughts about the ending that I wrote a separate post so we can discuss it more in-depth. So head over there and let me know your impression of the ending and the book overall.

The Synopsis

In June, 1954, eighteen-year-old Emmett Watson is driven home to Nebraska by the warden of the juvenile work farm where he has just served fifteen months for involuntary manslaughter. His mother long gone, his father recently deceased, and the family farm foreclosed upon by the bank, Emmett’s intention is to pick up his eight-year-old brother, Billy, and head to California where they can start their lives anew. But when the warden drives away, Emmett discovers that two friends from the work farm have hidden themselves in the trunk of the warden’s car. Together, they have hatched an altogether different plan for Emmett’s future, one that will take them all on a fateful journey in the opposite direction—to the City of New York.

Spanning just ten days and told from multiple points of view, Towles’s third novel will satisfy fans of his multi-layered literary styling while providing them an array of new and richly imagined settings, characters, and themes.

Book Club Questions for The Lincoln Highway

1. Why do you think this book was titled The Lincoln Highway? What did the highway represent to several of the characters? Have you ever rode or driven on this highway?
2. The novel is told from multi-perspectives including Emmett, Duchess, Billy, Woolly, Sally, Ulysses and more. Why were all these perspectives included and what did it add to the story? On the same note, why were Duchess and Sally told in first-person and the others in third-person?
3. We learn that Emmett was sent to a juvenile work farm after he unintentionally killed a bully. How did this act of violence change everything for Emmett?
4. Emmett and Billy make plans to go to California for a fresh start. How would the book have been different if Woolly and Duchess never made an appearance? Would the brothers ever had found their mother in San Fransisco?
5. What was your impression overall of Duchess and his motivations? Did that change at all as the book went on? Do you believe he was simply misguided as a result of his upbringing or was there something more sinister at play with him?
6. It’s interesting that Duchess gets away with so much—even Emmett contains his anger with him, until the very end. Why did Duchess receive such leeway from others?
7. Do you see Emmett as the hero of the story and Duchess as the villain? Or is it more complicated than that? What are your thoughts about their contrasting ethics?
8. Why do you think the author chose to set the story in 1954 specifically?
9. Let’s talk about Billy’s book, “Professor Abacus Abernathe’s Compendium of Heroes, Adventurers, and Other Intrepid Travelers.” Why was the book so important to Billy and what did it teach him about being a hero?
10. Let’s talk about Woolly’s tragic story. Did you want to know more about his background and what drove his addiction? Was this trip a plan for him to eventually commit suicide from the start?
11. Why was Sally such a focus? Was she in love with Emmett or did she simply just want to get far away from home and having to take care of her dad?
12. What was your impression of the Ulysses storyline? Will he be reunited with his family? Why did Professor Abacus decide to follow him on the journey?
13. OK, we have to talk about the climax and ending! When Emmett finds Woolly is dead, he’s horrified, yet, Duchess is fairly nonchalant about it and only cares about the money. What does this say about Duchess’ character?
14. The two get into a fight and in a big twist, Emmett places a knocked out Duchess in a boat and it’s implied he puts Duchess there to delay him from trying to find the brothers. The boat contains a hole and Emmett stacks stones in order to stop the boat from flooding. However, once Duchess is awake and the money begins to blow away, Duchess shifts the boat to try and get it—causing it to sink and since Duchess can’t swim, he drowns. Did Emmett purposely try to kill Duchess? Or was he simply trying to delay Duchess from getting to them? Do you think the police will suspect Emmett once they find both Woolly and Duchess are dead or will Emmett live the rest of his life without knowing what happened to Duchess?
15. Before leaving for California, Emmett thinks: “Having come fifteen hundred miles in the wrong direction, on the verge of traveling three thousand more, Emmett believed that the power within him was new in nature, that no one but he could know what he was capable of, and he only has just begun to know it himself.” How do you interpret this line?
16. Overall, what are your thoughts about the book and the ending as a whole?
17. Do you have any favorite passages and/or quotes that stuck out to you?

Additional Recommendations

Hope you enjoyed book club questions for The Lincoln Highway! Here are some recommendations along with links to book club questions.

Thirteen-year-old Anna, an orphan, lives inside the formidable walls of Constantinople in a house of women who make their living embroidering the robes of priests. Restless, insatiably curious, Anna learns to read, and in this ancient city, famous for its libraries, she finds a book, the story of Aethon, who longs to be turned into a bird so that he can fly to a utopian paradise in the sky. This she reads to her ailing sister as the walls of the only place she has known are bombarded in the great siege of Constantinople. Outside the walls is Omeir, a village boy, miles from home, conscripted with his beloved oxen into the invading army. His path and Anna’s will cross.

Five hundred years later, in a library in Idaho, octogenarian Zeno, who learned Greek as a prisoner of war, rehearses five children in a play adaptation of Aethon’s story, preserved against all odds through centuries. Tucked among the library shelves is a bomb, planted by a troubled, idealistic teenager, Seymour. This is another siege. And in a not-so-distant future, on the interstellar ship Argos, Konstance is alone in a vault, copying on scraps of sacking the story of Aethon, told to her by her father. She has never set foot on our planet.

You can order the book on Amazon here. To support local bookstores, order on Bookshop here. Check out my book club questions here.

Somewhere out beyond the edge of the universe there is a library that contains an infinite number of books, each one the story of another reality. One tells the story of your life as it is, along with another book for the other life you could have lived if you had made a different choice at any point in your life. While we all wonder how our lives might have been, what if you had the chance to go to the library and see for yourself? Would any of these other lives truly be better?

In The Midnight Library, Matt Haig’s enchanting blockbuster novel, Nora Seed finds herself faced with this decision. Faced with the possibility of changing her life for a new one, following a different career, undoing old breakups, realizing her dreams of becoming a glaciologist; she must search within herself as she travels through the Midnight Library to decide what is truly fulfilling in life, and what makes it worth living in the first place.

You can order the book on Amazon here. To support local bookstores, order on Bookshop here. Check out my book club questions here.

Happy reading!