The memoir opens with a scene from Cheryl's hike: it is the summer of 1995, and she has been on the trail for 38 days and has reached northern California. In pain, she removes her hiking boots and one of them accidentally falls off the mountain pass she is hiking. The moment causes her to reflect on how she got there. Cheryl is twenty-six, with a painful family history: she is estranged from her father, and her mother is dead. Her relationship with her stepfather and siblings is shaky, and she has found it difficult to settle in any one place. She is now hiking the Pacific Crest Trail, which runs through California, Oregon, and Washington. The idea first came to her seven months earlier while she was working as a waitress in Minnesota. She happened across a guidebook to the Pacific Crest Trail and bought it on a whim, curious. Impulsively, Cheryl decided she would hike the trail.
Cheryl traces the origins of her decision back to her mother's illness and death. More than four years earlier, when Cheryl was twenty-two, her mother was diagnosed with lung cancer. Cheryl was shocked because her mother was only forty-five and had always been very healthy. Cheryl recalls the day of her mother's diagnosis, when she accompanied her mother and her stepfather, Eddie, to the clinic in Minnesota. The shock and grief were particularly intense because Cheryl had always had a close relationship with her mother. Cheryl is the oldest of three children, with a sister named Karen and a younger brother named Leif. Her mother, Bobbi, got married at 19 while pregnant, to a man who turned out to be abusive. She stayed with Cheryl's father until she was 28, at which time she left her husband and took her three young children with her.
Bobbi struggles to make ends meet for her children, but she remains positive and loving. When Cheryl is 9, Bobbi meets Eddie, whom she falls in love with and marries. After the marriage, Bobbi, Eddie, and the children buy a property of land in rural Minnesota, where they live in rugged conditions. The family eventually moves into a home they have built themselves, and Cheryl sees the roots of her ability to survive in varied conditions originating in this childhood experience. She eventually goes on to college at a school called St. Thomas, and this experience awakens her mother's curiosity in higher education. Bobbi ends up enrolling at college as well, and mother and daughter eventually transfer from St. Thomas to the University of Minnesota. They are both in their senior year when Bobbi is diagnosed. Cheryl is living in Minneapolis and has married a man named Paul.
Of all her siblings, Cheryl plays the most active role in caring for her mother during her illness. Her mother declines much more quickly than anyone anticipated, and Cheryl is frustrated by her brother's absence. On St. Patrick's Day, knowing her mother does not have much time left, Cheryl leaves the hospital to go and look for him. She tracks down Leif and the two of them arrive at the hospital the next morning to learn that their mother died an hour earlier.
In June 1995, before she begins her hike, Cheryl visits Minneapolis to see her mother's grave. From there, she drives to Portland, where she leaves a set of boxes that her friend will mail to predetermined stops along the trail. Cheryl then flies from Portland to Los Angeles and drives to the town of Mojave, where she will begin her hike.
Cheryl checks into a motel room in Mojave, feeling lonely. Her relationship with Eddie declined after her mother's death, and she is now divorced from Paul. A few weeks after her mother's death, Paul had been accepted into graduate school in New York. Cheryl was unwilling to leave Minnesota since she felt her family needed her, so they deferred the offer. However, Cheryl had also started to kiss other men. When they moved to New York in 1992, she vowed to focus on being faithful. However, Paul quickly dropped out of his program, and they ended up going on a long road trip. In spring of 1993, they found themselves in Portland where they both got jobs in restaurants and Cheryl tried to stop seeing other men. Only a few months later, Paul returned to Minneapolis to work, leaving Cheryl in Oregon, where she began having full-blown affairs. In the winter of 1994, three years after her mother's death, she finally told Paul what has been happening. The two of them separated without a clear plan of what would happen next. Lonely and frustrated, Cheryl agreed to return to Portland to visit her friend Lisa. In the summer of 1994, Cheryl drove alone from Minneapolis to Portland.
Cheryl is concerned because she lacks previous backpacking experience. She has done her best to prepare, but when she gets dressed for her first day on the trail, she realizes she cannot lift her pack because it is so heavy. She plans to spend about 100 days walking to her destination of Ashland, Oregon. Cheryl is filled with trepidation, but she is fiercely determined as she sets off.
The memoir works with two parallel narratives, introducing readers to both Cheryl's present reality of hiking the PCT and her past. The two narratives are deeply intertwined because it immediately becomes clear that Cheryl's past is what has led her to take on her grueling journey. Although she lacks backpacking experience and is not an experienced hiker, her roots of living close to the land extend back to a childhood where she regularly lived without electricity and running water. Cheryl's sense of who she is has been deeply intertwined with her relationships. Being a sibling, a daughter, and a wife have given her life purpose and structure, but she has now come untethered from all of those roles. Given what she has experienced, it is also easy to forget that Cheryl has not yet turned twenty-seven when she starts her hike. No matter what her past, she would likely be grappling with questions of who she truly is at this stage in her life.
The two relationships that have most impacted Cheryl's decision to begin her hike are profound ones: her relationship with her mother, and her relationship with her former husband. Although Cheryl makes it clear that there were tensions and disagreements with her mother, Bobbi's unconventional life made her an even more dominant part of her children's identity. Cheryl's confidence that she can do something as challenging as hiking the PCT, even with very little preparation, seems rooted in how her mother made her feel capable, valued, and able to achieve her dreams. Perhaps because Bobbi was a young mother, she and Cheryl also shared a relationship that had echoes of friendship and sisterhood. They lived through defining experiences together, like going to college side by side, and this parallel makes it seem even crueler that Bobbi's life was cut short when she was so young.
Before we see Cheryl grapple with the harsh, unrelenting nature of the trail, we see her face the equally harsh reality of a fatal illness. For a young woman with a bright future, it seems almost inconceivable that she could find herself totally helpless and unable to take actions that will change an outcome. Cheryl's fury and frustration in the face of her mother's illness contrast with the older woman's state of acceptance. Because she has lived longer and suffered more, Bobbi is better able to understand that sometimes events happen that are beyond our control. The fast pace of Bobbi's illness means Cheryl didn't have time to learn this lesson while her mother was dying. Both the illness and Bobbi's death itself were too sudden and too disconnected from anything Cheryl had experienced up to the point for her to able to process or move beyond them.
The inability to cope with grief is exhibited through Cheryl's behavior, leading her to become increasingly alienated. Most people would hope that a loss would draw them closer to their partner, and Cheryl never criticizes Paul's attempts to be loving and supportive. Still, he was very young and had lots of hopes and ambitions, which inevitably drew him towards a forward momentum rather than the retreat and isolation Cheryl craved. Her infidelity might be viewed as a kind of masochism: even though she knows it will only hurt her marriage, and therefore herself, Cheryl can't stop herself from pursuing emotionally empty promiscuity. She doesn't reflect on these affairs as sexually satisfying, and the brevity with which she simply notes the partners she slept with indicates a kind of hollow detachment towards this behavior. She wants an outlet for her pain, but she ends up enacting her fear of abandonment by driving her husband away.
And yet, while Cheryl's behavior over the past 4 years seems to have indicated an inability to follow through on commitments or remain settled on any single course of action, she is now showing intense commitment to meeting a demanding goal. As hard as it is, completing her hike seems less hard than some of what she has already tried to make herself do: resist infidelity, negotiate her feelings with the family members who have drifted away, and find a sense of who she is and what she wants for herself. Cheryl's stubborn determination to manage a pack she can't even lift is a reader's first taste of the intense determination she will show through the rest of the memoir.