Printable Book Club Questions for The Lincoln Highway by Amor Towles

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?
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?
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?
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?
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?
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?
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?
Why do you think the author chose to set the story in 1954 specifically?
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?
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?
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?
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?
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?
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?
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?
Overall, what are your thoughts about the book and the ending as a whole?
Do you have any favorite passages and/or quotes that stuck out to you?