The Ride of Her Life: The True Story of a Woman, Her Horse, and Their Last-Chance Journey Across America

1. General Impressions

Gather initial thoughts and broad opinions about the book.

• Discuss your overall impressions of The Ride of Her Life? What aspects of it did you like most and least? How does it differ from other biographies you’ve read?
• How does the book compare to Elizabeth Letts’s other books, such as the novel Finding Dorothy? What does Letts’s background have in common with Annie Wilkins’s story?
• Discuss why Annie Wilkins chose to traverse the country on horseback despite her illness and the inherent dangers of modern roads and highways.

2. Personal Reflection and Connection

Encourage readers to connect the book’s themes and characters with their personal experiences.

• Reflect on any parts of The Ride of Her Life that evoked a strong emotional response (for example, instances involving accidents or exemplifying human kindness). Why did they elicit this response?
• Some readers have taken issue with Annie’s apparent disregard for the welfare of the animals she claimed to love deeply (her horse Tarzan; her dog, Depeche Toi; and later her second horse, Rex). Do you agree? If not, what makes Annie’s choices understandable?
• Discuss how the book’s themes (which center on resilience and hope in the face of extreme hardships, the kindness of strangers, human kindness, and human-animal bonds) relate to your personal views or experiences.

3. Societal and Cultural Context

Examine the book’s relevance to societal issues, historical events, or cultural themes.

• The Ride of Her Life illuminates the consumption-based and youth-focused priorities of modern capitalist society by presenting a contrasting picture. An elder with a terminal illness, Annie was experiencing severe financial hardships when she set out on her journey, and she prioritized simple goals, bare necessities, and relationships over material wealth. As she traveled, she often slept in jails and sometimes rejected offers that would have made her journey more comfortable. What do her choices say about American values?
• Discuss the impact of Annie’s story in relation to the historical era in which she lived. The 1950s was a time of great suburban expansion, many new infrastructure projects (such as highway and bridge construction), and rampant consumerism in the US. Annie’s approach to life and travel did not engage with these aspects of modern society. Discuss how this difference contributed to her journey’s appeal and impact in communities and the media, how it affected her experiences, and why it adds interest to the book.
• Consider parallels between Annie’s life and the Quaker lifestyle in the modern world. How did her lifestyle and values resonate with theirs? Did her motivations to forgo modern comforts, as if she were living in an earlier period, differ from those of the Quakers? If so, in what ways?
• Discuss Annie’s reaction to becoming a media celebrity. Did the degree to which she became open to it surprise you?

4. Literary Analysis

Dive into the book’s structure, characters, themes, and symbolism.

• Examine the cryptic yet colorful chapter titles in The Ride of Her Life. How do they reflect Annie’s personality and the nature of her journey?
• Discuss The Kindness of Strangers as a theme. Even before the media began following Annie’s journey, people along her route (such as Laurence and Nellie Bennett and Jean Lane) reached out to offer shelter, food, and other gifts. What made her relatable enough that people and communities did so? What was it about her journey that resonated with them?
• Identify and discuss symbols and motifs within the book, such as animals, paved roads, signs, landmarks, and weather. What do they represent?
• Discuss the impact of Annie’s route choices on the book’s tone.

5. Creative Engagement

Encourage imaginative and creative connections to the book.

• If this book were adapted into a movie, who would you envision playing the roles of Annie and the other important figures? Consider her many hosts, including the Bennetts and Jean Lane (early in her trip), Millie and Carney Rose in Pennsylvania, the Richards in Kentucky (who gave her the horse Rex to lighten Tarzan’s load), Harvey Kelsey in Wyoming (who startled her by proposing marriage), and the Eisenhowers in Oregon (with whom she stayed for months). Also consider Mina Sawyer (the reporter from Maine) and Art Linkletter (the TV personality who compensated her richly to appear on his show).
• Create a playlist, collage, or poem that captures the mood or themes of the book or reflects various figures in it. Discuss the choices that went into its creation.
• Research Annie’s route and determine how roads and route options across the US have changed since she completed her journey. Then imagine how Annie’s journey would differ if she were to make it in the current era, considering climate and seasonal weather differences, safety, and any other variables, and map the route you’d suggest.

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