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The Lincoln Highway Book Club Questions & Discussion Guide

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Transporting the reader back to the 1950s, with a story stretching from the Midwest to both coasts, The Lincoln Highway by Amor Towles has made nearly every major “best of” literary list in 2021. Much like the titular Interstate, The Lincoln Highway spans the country, connecting the stories of five young characters in Midcentury America, and presenting a slice of a time that was in no way simple.

This book is not a quaint portrait of a romantic era. Rather, The Lincoln Highway is a layered journey about the burdens of expectations, the grief of lost dreams, and the meaning of home. 

The Lincoln Highway: Book club questions. book cover in library

The Lincoln Highway offers a beautiful journey for any book club, appealing to readers of all ages and backgrounds. Fans of the author’s other works will likely even notice sly connections to Towles’ other characters!

These The Lincoln Highway book club questions can help your book club navigate the winding roads of the many characters and themes throughout the novel. This The Lincoln Highway discussion guide also includes a synopsis, selected reviews and discussion prompts.

We’ve also got three suggested books like The Lincoln Highway for you to read next.

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The Lincoln Highway Synopsis

The Lincoln Highway, by Amor Towles

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.

10 The Lincoln Highway Book Club Questions

  1. Every character–main and secondary–in this novel has a dream. Some are big and some are simple, but all of the hopes and dreams have collateral consequences. Whose dreams do you think had the biggest impact on the rest of the characters? Whose dreams do you identify with most?
  2. The Lincoln Highway is full of expectations based on class, gender, and race. The burden of expectations can be heavy. Discuss how expectations affect the character’s choices. How have others’ expectations of you changed the decisions you’ve made in your life? What expectations might have been on you, if you were a young adult in the 1950s?
  3. Duchess spends much of the novel concerned with settling moral debts both owed and owed to him. Do you agree with his idea that the universe is keeping score in some way? Do you think he deserved the ending he got? What do you think his life would have looked like if he had known how to swim?
  4. By all accounts, Wooly lived a life of privilege unlike any of the other characters. But, Wooly was very different than the other boys. In today’s world, Wooly might have been diagnosed with a mental health or cognitive condition and received treatment.  If Wooly were alive today, how do you think his journey might have ended? How have we made progress in the treatment of young adult mental health, and where is there progress yet to be made?
  5. A central theme of The Lincoln Highway is ambition–wanting more than you were born into. What do you think happened to Emmett and Billy’s mother? Where do you think she is now? Besides the boy’s mother, Sally serves as the central female character in the book. What do you make of the relationship between Emmett and Sally? What do you think happens to Sally after the novel ends?
  6. One of the criticisms of the book is the depiction of Billy as overly precocious beyond his years. Have you ever known a child like that? Were you a child like that? Do you think Emmett was fit to be a caregiver for his younger brother?
  7. The Lincoln Highway is a book about metamorphosis. Which character do you think transforms the most over the course of the book?
  8. Even though there are a handful of central characters, the novel introduces many secondary characters along the journey. Of those, who do you most identify with? Which of the supporting characters would you like to read a full novel about?
  9. The era of the book almost functions as another character — what themes in the book do you think are unique to the time period, and which ones do you think would persist if the novel took place in modern times?
  10. With all that happens in the novel, it’s hard to believe it only spans 10 days. What were the most memorable 10 days of your life? Why do you think the author chose to constrain the story to this limited amount of time? 

Selected Reviews for The Lincoln Highway

“Amor Towles spins a beguiling and rollicking historical adventure set in the 1950s, brilliantly imaginative, and with an unforgettable cast of character…A superb novel that I recommend highly, a wonderful must read.” 

“A meandering, long-winded adventure with too many side stories. But the characters, especially Emmett and Billy, kept me reading. The novel moves along at a steady clip and I mostly enjoyed the ride.”

“Amor Towles is a gifted storyteller. The trouble here was that he couldn’t seem to decide which story he wanted to tell. So he told them all. In one novel. What it felt like to me was that he knew a lot of odd and eccentric things about the early to mid-20th century, and he wanted to find a way to include them all in the book.”

“Wit, humor, intrigue, sophisticated storytelling, a flawless command of style, fascinating and compelling characters, splendid atmosphere, exquisite insight into human behavior-it’s all here.”

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3 Books Like The Lincoln Highway

If you are keen to read more historical perspective on the Black American experience, consider The Revisioners by Margaret Wilkerton Sexton. It features a multigenerational story set in 1920’s rural Louisiana and present day New Orleans. We have a book club guide for The Revisioners, which also has some additional related reading suggestions.

The Lincoln Highway is also a Read with Jenna book club pic. If you like her suggestions, you can also check out recent pics like The Dutch House, Great Circle and Dear Edward. We also have a guide for Towle’s A Gentleman in Moscow.

And here are three more books like The Lincoln Highway:

Rules of Civility book cover Amor Towles

Rules of Civility, by Amor Towles.

Another of the author’s works that dives into a unique era in American history–the late 1930’s. This book explores many of the same themes as The Lincoln Highway–expectations, ambition, class and family–set amongst the backdrop of a New York City emerging from the depression. 


As I Lay Dying Faulkner book cover

As I Lay Dying, by William Faulkner.

A classic novel told from multiple points of view, this book tells the story of a family’s journey to their dead matriarch’s hometown as they venture to fulfill her wish to be buried in Jefferson, Mississippi. The many characters are shaped not only by their internal dialogue, but also by the way we see them through the eyes of others. 


Colson Whitehead Harlem Shuffle book cover

Harlem Shuffle, by Colson Whitehead.

New York City takes center stage in this novel, set in the early 1960’s, where the Black experience in a changing neighborhood illuminates the internal struggle between ambition and safety. Although the lives of the characters in Harlem Shuffle are profoundly different than those in The Lincoln Highway, Whitehead explores many of the same themes: class, greed, and the hunger to make something out of a life where the deck seems stacked against you.

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About Sarah Martin
Sarah is a book-lover who, by day, is Vice President of a technology company that specializes in storytelling. She is also a writer, educator and speaker on all things related to health and social justice. When she isn’t working or writing book club questions, you can find her reading (obviously), dancing on her church dance squad, out on a long run with her German Shepard, or experimenting in the kitchen.

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