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Discussion Guide

The Ride of Her Life

In 1954, sixty-three-year-old Maine farmer Annie Wilkins embarked on an impossible journey. She had no money and no family, she had just lost her farm, and her doctor had given her only two years to live. But Annie wanted to see the Pacific Ocean before she died. She ignored her doctor’s advice to move into the county charity home. Instead, she bought a cast-off brown gelding named Tarzan, donned men’s dungarees, and headed south in mid-November, hoping to beat the snow. Annie had little idea what to expect beyond her rural crossroads; she didn’t even have a map. But she did have her ex-racehorse, her faithful mutt, and her own unfailing belief that Americans would treat a stranger with kindness.

Annie, Tarzan, and her dog, Depeche Toi, rode straight into a world transformed by the rapid construction of modern highways. Between 1954 and 1956, the three travelers pushed through blizzards, forded rivers, climbed mountains, and clung to the narrow shoulder as cars whipped by them at terrifying speeds. Annie rode more than four thousand miles, through America’s big cities and small towns. Along the way, she met ordinary people and celebrities—from Andrew Wyeth (who sketched Tarzan) to Art Linkletter and Groucho Marx. She received many offers—a permanent home at a riding stable in New Jersey, a job at a gas station in rural Kentucky, even a marriage proposal from a Wyoming rancher. In a decade when car ownership nearly tripled, when television’s influence was expanding fast, when homeowners began locking their doors, Annie and her four-footed companions inspired an outpouring of neighborliness in a rapidly changing world.

These book club questions are from the publisher, Random House Books. A full book club kit can be found here

Book club questions for The Ride of Her Life by Elizabeth Letts

Use these discussion questions to guide your next book club meeting.

The quotes at the start of each chapter were carefully chosen by the author to convey something about the mood or action in the pages to come. Did any of them particularly stand out to you?
This book, in part, recognizes the kindness of strangers along Annie’s journey. Have you ever experienced a such kindnesses from strangers? Tell us about it/them.
Annie has a special bond with all her animals. She instantly bonds with the horses Tarzan and Rex—and Depeche Toi is her loyal shadow. Have there been special animals in your life?
Did Annie’s story inspire you to travel? If so, where will you go?
As an older woman, traveling alone, Annie was not a typical solo traveler of the era, but as a white person she didn’t come up against the kinds of hazards that Black Americans faced during her era. How would her journey have been different for a person of color? Is it easier or harder to make a journey like Annie’s today, or does it depend on who is making the journey?
What was your initial reaction when Annie decided to ride Tarzan from Maine to California? Have you ever tried anything that other people laughed at or said was impossible? Did Annie inspire you to strike something new off your bucket list?
How did Annie defy the expectations of women in the 1950s? Or even those of today?
What was one of your favorite moments during Annie’s journey? Why did it resonate with you?
Annie spent months travelling across the country with her animal companions. Aer our collective time in lockdown, do you have a new appreciation for the company of animals? How do you think you and your animals would do on the road?
Before reading the book, had you heard about Annie? Were you surprised this story isn’t more well known?
Setting plays a big role in the plot—from Annie’s farm in Maine to sitting in the saddle on the highway to ending up in a new friend’s home. Why do you think setting is so important? Which setting was most appealing to you?
Does the author use language in a way that’s different or striking? How did she capture the feel of the 1950s and the difficulty of Annie’s journey? What style or “voice” does the author use?

The Ride of Her Life Book Club Questions PDF

Click here for a printable PDF of the The Ride of Her Life discussion questions