Gather initial thoughts and broad opinions about the book.

1. How did learning about Emma’s history of domestic abuse so early in the book shape your reading of her journey? Did it change what her walk represented for you?

2. The story of a woman undertaking a long hike to process trauma and find herself might remind you of Cheryl Strayed’s memoir, Wild. How would you compare Emma’s motivations and experiences in 1955 with Strayed’s much later journey on the Pacific Crest Trail?

3. What was the most memorable aspect of Emma’s story for you? Was it her physical endurance, her interactions with strangers, her quiet defiance, or something else entirely?

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

1. Emma often relied on creativity and determination rather than expensive equipment or careful planning. Have you similarly experienced having little equipment but determination to do something?

2. Throughout the book, Emma avoids fully explaining why she hikes, even after becoming famous. Have you ever found it difficult to share something publicly?

3. Emma spends much of the book walking alone, yet her journey also depends on the kindness of strangers. When have you experienced a sense of community among strangers?

4. Emma’s hike is framed as an act of Escape and Self-Liberation. Can you think of a time you sought out nature or a long walk to find perspective on a difficult situation? What is it about moving through a landscape on foot that can be so restorative?

5. Many people in Emma’s life underestimated or misunderstood her, especially because of her age and gender. Have you ever felt surprised by someone’s hidden strength or resilience after initially misjudging them?

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

1. Montgomery frames Emma’s journey as a quiet rebellion against the rise of car culture and a more sedentary 1950s America. In what ways do you see similar trends today, with technology and convenience shaping our lives? Does Emma’s story offer any lessons for contemporary society?

2. How does the narrative place Emma’s personal journey within the broader anxieties of the Cold War era? Does her accidental entry into a secure Air Force station or her peaceful night in a shelter with an integrated group from Harlem tell you anything about the America she was walking through?

3. Emma’s celebrity is credited with helping save the Appalachian Trail by drawing national attention to its disrepair. Do you think a single individual’s story can still have that kind of impact on conservation or other major issues today? Why or why not?

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

1. The author weaves Emma’s 1955 hike together with flashbacks to her abusive marriage. How does this dual timeline shape your understanding of her character and motivations as the story unfolds?

2. The guide contrasts Emma’s experience with Henry David Thoreau’s view of the wilderness as “savage and awful” (188). How does the book position Emma’s journey within the larger tradition of American nature writing? Does her perspective as a survivor offer a different kind of truth about the outdoors?

3. The motif of shelter is explored throughout the book, from dilapidated lean-tos to the porches of strangers. How does this recurring search for refuge develop the book’s central themes of vulnerability and human connection?

4. Emma’s public persona as a plucky, widowed grandmother contrasts sharply with the violent reality of her past. How does the author use newspaper articles and media appearances within the narrative to explore this tension?

5. Based on the evidence presented, do you agree with the book’s subtitle, which claims Emma “Saved the Appalachian Trail”? How does Montgomery build the case for her lasting legacy beyond her personal accomplishments?

Encourage imaginative and creative connections to the book.

1. The Buckeye Trail in Ohio features a section named the “Grandma Gatewood Memorial Trail.” You’ve been asked to design a historical marker for the trailhead. What key aspects of her life and journey would you highlight in a brief inscription, and what imagery would you use to capture her spirit?

2. What do you think Emma recorded in her trail diary beyond the practical details of her hike? Create a short, hypothetical entry from her perspective after a particularly challenging day, like crossing the flooded Clarendon Gorge or navigating Mahoosuc Notch.

3. Suppose you had the chance to hike a single day with Emma on the trail. What part of her journey would you choose to join her on, and what one question would you ask that the reporters in the book never did?