Cheryl faces her first obstacle as soon as she leaves the motel in Mojave: she has to hitch a ride to get to the trailhead. Two men pick her up, and she fumbles through the embarrassment of dealing with her heavy backpack. Cheryl feels a sense of pride and elation as she sets off, but she quickly realizes how difficult it is hard to hike in the hot and dry conditions while carrying a heavy pack. As she walks, Cheryl thinks back to December of 1994. She and her friend Aimee were in South Dakota to retrieve Cheryl's truck and she went to an outdoor supply store to buy a snow shovel. While there, she saw a Pacific Crest Trail guidebook for the first time, but she didn't think much of it. However, later that day, Cheryl began to suspect that she might be pregnant.
The father of her child was Joe, a man Cheryl met in Portland in the summer. Shortly after she and Joe had begun sleeping together, he had introduced her to heroin. Lisa had tried to intervene, but Cheryl had brushed off her concerns. Lisa had then called Paul and told him what was happening, so Paul went to Portland. At first, Cheryl had been resistant to him intervening in her life, but later that day, she was robbed at knifepoint. Shaken, Cheryl had abruptly left Portland and returned to Minneapolis with Paul in late September 1994. A few weeks later, Joe had gone to visit her; during his visit, Cheryl had slept with him and also done heroin. She had intended to turn her life around when he'd gone, so she was surprised to realize she was pregnant. Driving back to Minneapolis, Cheryl grieved over everything that had happened since her mother's death. As soon as she arrived, Cheryl bought a copy of the guidebook and began preparations for her hike.
Cheryl has brought the guidebook with her on the hike, but looking through it on the trail just makes her more nervous. She has also brought a book about using a compass, a book of poetry by Adrienne Rich, and a Faulkner novel. On her first day on the trail, Cheryl pitches her tent early. She sets off the morning of the second day, planning to hike the remaining thirteen miles to her first water source at Golden Oak Springs. However, she realizes the terrain is more challenging than she expected, the weather is unpredictable, and she is making much slower progress than she anticipated. She also faces the embarrassing challenge of finding herself unable to dig the hole she had planned to defecate in.
Cheryl reaches Golden Oak Springs on Day 3 of her hike. She refills her water supply and then lingers there. She reflects on how, only 2 days before beginning her hike, she had taken heroin with Joe in Portland. Cheryl is in pain but begins Day 4 feeling hopeful when she leaves Golden Oak Springs. New obstacles emerge: she falls and injures her leg, and she has to climb over a number of fallen trees. On Day 5 on the trail, she is frightened by an encounter with a moose. She is averaging about 9 miles per day and is concerned about this slower pace. On Day 8, Cheryl assesses her food supply. Her next supply stop is in Kennedy Meadows, 135 miles away. Her stove is also not working, so she can't eat any food that requires preparation. Cheryl decides to leave the trail and head in the direction of the highway she knows runs parallel to the trail. She begins following a Jeep road and eventually comes across three men. They're preparing to dynamite-blast a mountain as part of a mining operation. One of the men, Frank, agrees to take Cheryl back to his place so she can spend the night there before repairing her stove.
During the drive with Frank, Cheryl becomes nervous and tells a lie that her husband Paul is waiting for her in Kennedy Meadows, even though she has been divorced since April. She and Paul marked their divorce by getting matching tattoos. At Frank's home, she meets his wife, Annette, and gratefully eats dinner. Cheryl recalls that she technically never completed her college degree since she was too grief-stricken to write a final English essay. The next morning, Frank leaves Cheryl on the highway to hitchhike to a town called Ridgeway. She is picked up by a man named Troy, who delivers chips, and he takes her to an outdoor supply store. After getting her stove repaired, Cheryl decides to stay in Ridgeway for the night, and she checks in to a motel. The clerk at the hotel tells Cheryl that the Sierra Nevada mountains still have a lot of snow, which is worrying news to Cheryl.
Nonetheless, the next day, she returns to the trail when she gets a ride to Walker Pass. She has to cover 52 miles to Kennedy Meadows, and 16 to her next water source. As she hikes, the conditions become more difficult, with Cheryl encountering rock slides and blistering heat. By the time she arrives at the next water source, Spanish Needle Creek, Cheryl has decided to quit. She plans to walk to the next road, and then veer off the trail and follow the road until she finds someone to give her a ride. However, before she arrives at the road, she runs into a fellow hiker named Greg. Greg is much better prepared than Cheryl and is encouraging to her. He is concerned about the unusually snowy conditions, but he is hopeful. He is going to be spending a few days in Kennedy Meadows, and he tells Cheryl that he will catch up with her there so they can formulate a plan. After they part ways, Cheryl decides to continue with the hike.
As Cheryl continues to hike towards Kennedy Meadows, she thinks about the ice ax that is awaiting her in her supply box, and how she does not actually know how to use it. She also encounters her first bear on the trail. On the morning of Day 14, the day she is scheduled to reach Kennedy Meadows, Cheryl encounters two hikers named Albert and Matt. She thinks about how she adopted her new last name of Strayed after her divorce was finalized, and how it now symbolizes her wandering ways. Cheryl married Paul when she was nineteen, and the two of them lived an adventurous and happy life until her mother's illness. She still feels sad when she thinks about the end of her marriage.
When Cheryl arrives at Kennedy Meadows, she retrieves her box from the General Store and also receives a postcard from Joe. She has the good fortune to find a ski pole that is being given away, and she takes it with her. Cheryl arrives at the nearby campground and meets a man named Ed, who tells her that Greg, Matt, and Albert have already arrived. Happy to be reunited, Cheryl enjoys a good meal. She is delighted to receive new clothes and books in her supply box, but she is concerned about the weight of her pack. Albert offers to help her weed out some of the items she is carrying, and Cheryl is embarrassed when he finds the condoms she has been carrying. However, she is delighted to have a lighter pack.
At the campsite, Cheryl meets two hikers named Tom and Doug, who have been hiking just a bit behind her and know her name from the trail registers. Cheryl is relieved that, like her, they don't seem to be seasoned hikers. Together, all the hikers discuss how to deal with the unusually snowy conditions, but Cheryl is determined to see if she can hike through the mountains. Greg teaches her how to use the ice ax. Unfortunately, Matt and Albert have fallen ill and have to abandon their hike. Cheryl plans to resume her hike with Tom and Doug, and Greg is likely to catch up to her on the trail. Before she leaves the campground, Cheryl realizes that someone has taken the condoms she removed from her pack.
As Cheryl begins her hike, it is clear that she did not fully understand what she was taking on. Her brash confidence begins to slip when she contends with the reality of what hiking the trail will be like, and also how long she is going to have to endure the harsh trail conditions. The planned duration of her hike is a similar length to the duration of her mother's illness. Cheryl is not only worried about her competence as a hiker: she also faces particularly challenging conditions. She could not have anticipated that the snow conditions would be particularly bad, another example of a circumstance that is beyond her control and yet impactful. Cheryl is also acutely conscious of two other factors that set her apart from the other hikers: she is hiking alone, and she is a woman. The former is rare, but not unknown. Cheryl meets other solo hikers, such as Greg. Nonetheless, the awareness that many other hikers have a friend or family member to make this journey, which highlights her own solitude in the world. Cheryl has sought out the chance to be alone, but even if she wanted a companion for her journey, she doesn't have anyone in her life who would be a likely candidate.
Cheryl's gender is a stronger distinguisher. She takes pride in the idea of hiking the trail as a woman alone. Part of what she wants to reclaim through her journey is a connection to her mother and the heritage of independence and fortitude she observed in Bobbi. Bobbi was a single mother who fled an abusive relationship; she walked a different kind of journey, but she also chose to be brave and self-reliant in her own way. Cheryl is convinced that she can be just as tough as any man on the trail, but she also knows she is exposed to different dangers. Any time she enters into a vehicle with one or more men, Cheryl is acutely aware of risk and vulnerability. It seems clear from the beginning that if Cheryl is going to be truly threatened by anything in the trail, it will be human men.
Yet, as readers learn more about her past, it also becomes clear that Cheryl has posed a significant danger to herself, even in the very recent past. Her heroin use shows the extent to which she was seeking something to numb her pain and grief. Cheryl doesn't portray herself as an addict, but she clearly finds it difficult to abstain from drug use when the opportunity presents itself. While the trail demands sacrifice and rigid self-discipline from her, it also protects her from certain temptations. She won't be able to drown her pain in sex and drugs; she'll have to face it every day. Cheryl's visceral physical experience of the trail, including her bleeding feet and aching muscles, becomes a new sort of painkiller, but, unlike sex and heroin, they force her to face herself rather than running away from her experiences. While the other releases she sought may have numbed the pain, the physical pains of the trail drown it out.
Along with the drug usage, readers also learn that Cheryl experienced an unplanned pregnancy and abortion a few months before beginning her hike. She doesn't discuss her thought process around the choice, but as someone young, single, financially unstable, and deeply unhappy, it seems that Cheryl assessed herself as not yet ready to become a mother. There also seems to be an implicit contrast between her and Bobbi: Cheryl feels disconnected from her mother's memory and unworthy of her identity as a daughter. Until she can claim and reconcile this, it seems unlikely that she will be ready to move into a role where she can nurture and provide unconditional love to a child of her own.
Along with Cheryl's lack of preparation, she also clings to two aspects of her normal life, even though they seem an awkward fit with the realities of trail life. Cheryl insists on carrying condoms with her even though the chances of her encountering a prospective sexual partner seem slim. Even she admits, as she copes with a new relationship to her body, that her sexuality might be temporarily shelved while she contends with the challenges of the hike. Cheryl also stubbornly brings books with her, showing that she is also attached to her intellectual and imaginative identity. Unlike the condoms, the books get constant use, giving Cheryl a lifeline to a sense of normalcy. Especially given her position as a writer, the decision to give herself access to books reveals something about Cheryl's deepest values. She uses the trail to find herself, not just because of the journey, but also because of how it forces her to strip her life down to the barest essentials. She also has to focus on how simple, mundane tasks suddenly become complex: "Wild exemplifies the transformation of a broad idea or goal (changing one’s life/oneself via dramatic, new experience) into a series of rational actions or steps" (Brown 364).