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Quick answer: Good discussion questions for The Lincoln Highway by Amor Towles focus on brothers and family, choices and consequences, the stories we tell ourselves, friendship and loyalty, and a 10-day journey across 1950s America. Below are 18 questions grouped by theme, plus a spoiler-free summary.
Quick facts
Author: Amor Towles
Published: 2021
Setting: Nebraska, the rails and New York, June 1954
Structure: ten days, told by several narrators
Content note: violence, suicide and child abuse
The Lincoln Highway is Amor Towles’s third novel, and it’s a big, warm, adventurous road story that book clubs love to debate, especially its ending. It follows four young men and one small boy over ten days in June 1954, through a series of detours that keep sending them in the wrong direction. Behind the adventure are serious questions about fairness, loyalty and the stories we tell about our lives. This guide includes a spoiler-free summary, characters and themes, and 19 discussion questions grouped by theme. The questions contain spoilers, including the ending.
Table of Contents
Spoiler-Free Summary
In June 1954, 18-year-old Emmett Watson is driven home to Nebraska by the warden of the juvenile work farm where he has just served 15 months for involuntary manslaughter. His mother left long ago, his father has died, and the family farm is being foreclosed. Emmett plans to take his eight-year-old brother, Billy, and start over somewhere new.
Billy has his own plan: to drive west on the Lincoln Highway to San Francisco, where he believes their mother is. But two friends from the work farm, the charming, unpredictable Duchess and the gentle, troubled Woolly, have stowed away in the warden’s car.
Duchess and Woolly have a very different destination in mind, and soon Emmett’s beloved Studebaker is heading east toward New York instead. Over ten days, the travelers meet a gallery of unforgettable characters and face choices that will change their lives.
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Main Characters and Themes
| Character or Theme | What to Know |
|---|---|
| Emmett Watson | A steady, principled 18-year-old trying to start over |
| Billy Watson | Emmett’s eight-year-old brother, who loves stories of heroes |
| Duchess | A charismatic friend from the work farm with his own idea of fairness |
| Woolly Martin | A kind, fragile young man from a wealthy family |
| Sally Ransom | A neighbor who looks out for Emmett and Billy |
| Ulysses | A wandering WWII veteran Billy meets on the rails |
| Professor Abernathe | The author of Billy’s favorite book of heroes |
| Journeys | Detours, quests and what home means |
| Fairness and debts | Settling scores and making amends |
| Stories | How characters tell and believe their own stories |
Discussion Questions (Contains Spoilers)
Emmett and Billy
- Emmett believes in taking responsibility and not making excuses. How does that shape his choices?
- Billy’s book of heroes guides how he sees the world. How does it shape the story?
- Why is finding their mother so important to Billy, and what does Emmett think of it?
- How does Emmett’s relationship with Billy show what kind of man he is?
Duchess
- Duchess is charming and dangerous. Did you like him? Trust him?
- Duchess keeps a mental list of debts to settle. What does fairness mean to him?
- How did Duchess’s childhood and his father shape him?
- Duchess narrates in the first person while Emmett’s chapters are in the third person. Why do you think Towles made that choice?
Woolly
- What is Woolly searching for on this trip?
- How did you feel about Woolly’s fate? Did you see it coming?
- What does Woolly’s family’s camp in the Adirondacks represent?
Detours and Strangers
- Which of the people the travelers meet, like Ulysses or Professor Abernathe, stood out to you?
- How does Sally challenge the way the men around her see her?
- Why do you think Towles fills the book with so many detours?
The Ending and Big Picture
- What did you think of the choice Emmett makes about Duchess at the end?
- Some readers find the ending abrupt or unsettling. How did you feel?
- Is The Lincoln Highway an optimistic book?
- If you were writing chapter eleven, day eleven, what would happen next?
If you or someone in your group is struggling, you can call or text 988 to reach the 988 Suicide & Crisis Lifeline (US).
Book Club Ideas for The Lincoln Highway
- Serve 1950s diner food, like burgers, milkshakes and apple pie.
- Bring a map of the real Lincoln Highway and trace where the characters meant to go versus where they went.
- Share your favorite hero from childhood stories, the way Billy does with his book.
- Make a playlist of 1950s songs for the road.
Books Like The Lincoln Highway
If your group loved it, try A Gentleman in Moscow by Amor Towles for his most beloved novel, Rules of Civility by Amor Towles for 1930s New York, or James by Percival Everett for another great journey story.
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How to Structure Your Meeting
Start by asking which character everyone would want in the passenger seat on a long drive. Then work through two or three questions from each theme above, saving the “big picture” questions for the end. If your group is large, split into pairs for one theme and report back.
A simple 90-minute plan:
- 0–15 minutes: food, catch-up and the opening question.
- 15–60 minutes: the discussion questions, theme by theme.
- 60–75 minutes: one of the book club ideas above, or a quick comparison with the adaptation if there is one.
- 75–90 minutes: everyone rates the book out of five in one sentence, then you pick next month’s read.
Related: the best book club books for men and the best literary fiction books for book clubs.
Frequently Asked Questions
What is The Lincoln Highway about?
In 1954, 18-year-old Emmett Watson plans to drive west with his little brother, but two friends from a juvenile work farm hijack the trip toward New York over ten eventful days.
Is The Lincoln Highway good for book clubs?
Yes. It’s an engaging adventure with memorable characters, and its ending sparks plenty of debate.
Is The Lincoln Highway appropriate for all book clubs?
It includes violence, a suicide and references to child abuse, so share a content note before reading.
Is the Lincoln Highway a real road?
Yes. It was one of the first coast-to-coast highways in the US, running from Times Square in New York to San Francisco.