Cheryl only hikes a very short distance with Tom and Doug before sending them on ahead because she wants to be alone. She is now in her third week on the trail; it is late June, and she is ascending into the Sierra mountain range. She camps with the two men that night, but she hikes alone the next day. When Cheryl first encounters a patch of snow and ice, it becomes apparent to her that she will have to get off the trail at Trail Pass and bypass the highest and snowy part of the PCT. She tells Tom and Doug about her decision that night and her plan to go to Sierra City and rejoin the trail there. The two men discourage her from going off alone, but she insists. Cheryl thinks about how her plans will change by bypassing the High Sierra; she decides that she can now hike all of Oregon. Her new endpoint is the Bridge of the Gods, on the border of Oregon and Washington.
When Cheryl runs into Greg the next day, he tells her he is also bypassing. The two of them get off the trail at Trail Pass and hitchhike to a town called Lone Pine. Cheryl contacts Lisa to explain about the rerouting. Cheryl and Greg realize that, in order to get to Sierra City, they will have to take a Greyhound bus to Reno, and then another bus to Truckee, before hitchhiking to Sierra City. On the bus, Cheryl counts her money, becoming more and more worried. She will not receive more money until her next supply box in Belden Town, 96 miles away from Sierra City, and she does not think she can afford a motel in Sierra City. She and Greg arrive in Truckee, but they have a hard time getting a ride to Sierra City. When they finally do, they check into a motel. Cheryl is relieved to clean up, but she is disconcerted about the state of her body. When she tells Greg that she is losing toenails, he tells her that her boots must be too small.
That night, as Cheryl lies in her bed, she thinks about the time she met with a counselor named Vince to talk about her relationships with men. Cheryl recalls the pain of growing up with an inconsistent and abusive father. Nonetheless, Cheryl was sad when her parents divorced because she knew it meant she would lose contact with her father. Cheryl leaves her room; instead of knocking on Greg's door, she takes a long bath.
Outside of Sierra City, Cheryl and Greg rejoin the trail and part ways. She is concerned because this stretch of trail is still very snowy, and she becomes disoriented and unsure of whether she is still on the PCT. Cheryl briefly considers returning to Sierra City and bypassing even further, but she decides to stay on the trail. Four days after leaving Sierra City, Cheryl has covered 43 miles and has another 55 miles left to go before reaching Belden Town. She knows she will run out of supplies and finds the snowy conditions unbearable, so when she comes to a road, she veers off the trail and heads for a town called Quincy. Along the road, she is picked up by a car headed to Packer Lake Lodge; she accepts the ride, even though Packer Lake is in the wrong direction. When she arrives in Packer Lake, Cheryl also only has sixty cents because she has spent most of her money in Sierra City.
At the Lodge, a woman named Christine learns about Cheryl's journey and invites her back to the cabin where she is staying with her family. They give Cheryl a meal and suggest that she take a book with her. Cheryl is drawn to a novel by James Michener, who was her mother's favorite author. Christine drives Cheryl to the Quincy Ranger station, but they don't have any useful information about where to rejoin the PCT. Cheryl gets a ride with a group of young women to a point where the trail intersects with a road. On the drive, she thinks about her stepfather and how well he had gotten along with Cheryl and her siblings when he first started seeing her mother. However, within a short time after their mother's death, he had distanced himself and begun a new relationship.
When Cheryl is dropped off, she's disappointed to realize she will have to walk almost two miles before rejoining the PCT. It is late in the day, and Cheryl decides to camp for the night. However, she is woken up in the night by campground owners insisting that she has to pay if she wants to stay there. Cheryl is forced to hike in the night towards the trail. She makes camp only a short ways off and thinks about her mother's beloved horse, Lady.
Bobbi had purchased Lady when Cheryl was six, just after finally leaving Cheryl's father. Lady and a second horse eventually lived on the rural Minneapolis property, but when Cheryl visited in December 1993, years after her mother's death, she realized that Lady was elderly and ill. Cheryl and Eddie debated whether to pay a veterinarian to put her down or to shoot her themselves, and Eddie agreed to handle it. However, when Cheryl and Paul came back on Christmas Eve, Lady was still there. After speaking with her grandfather, Cheryl called her brother and Leif drove out to help. On the day after Christmas, Cheryl, Paul, and Leif took Lady out to shoot her, but the process was more grotesque and prolonged than Cheryl anticipated. After the horse was dead, Leif suggested that the spirit of their mother might now be able to pass into the next world.
The next morning on her current journey, Cheryl is still hesitant to return to the snowy PCT. She decides to walk back through the campground and along to Buck's Lake before rejoining the PCT at Three Lakes. At Three Lakes, Cheryl meets a group of friendly men who listen to her talk about the trail. One of them gives her a Bob Marley t-shirt. The next day, Cheryl continues on to the PCT, towards Belden Town. Despite challenging trail conditions, Cheryl reaches Belden and collects her box. She also meets two other women hiking the PCT: Trina and Stacy. The three women camp together, and they are joined by another hiker, a man named Brent. From this group, Cheryl learns that Greg grew frustrated by the snowy conditions and quit the hike.
That night, the hikers decide on their route to accommodate the continuing snow: they'll use a combination of roads and the PCT for the next fifty miles, and then bypass a particularly treacherous section by hitchhiking, before returning to the PCT at Old Station. Cheryl's next resupply box is 154 miles away, in McArthur-Burney Falls State Park. Before she goes to bed that night, Cheryl writes a letter to Joe and stargazes with Brent, reflecting on how far she has come and the journey that still lies ahead.
In large part, Cheryl's hike teaches her the value of determination and grit. However, it also shows her that adaptability and flexibility are equally powerful and necessary tools. Cheryl needs to regain a sense of empowerment, but that comes from knowing when to adapt to circumstances rather than persisting out of stubbornness. Her decision to bypass involves some disappointment and regret, but it also allows her to work within the confines of the reality of the conditions she is facing. Bypassing teaches Cheryl one of her most powerful lessons on the trail: achieving a goal can mean changing strategies, and things will seldom unfold exactly as predicted. So much of Cheryl's anger and grief is rooted in her inability to accept that, even though it was tragic and unfair, her mother got sick and died. Acceptance is part of what will set her free.
Along with the loss of her mother, it also becomes increasingly clear that Cheryl is grappling with her pain because of her estrangement from her father and stepfather. Her father was often a source of fear and distress in her childhood, yet she still mourns that the two of them were not able to develop her relationship. As she confronts her vulnerability on the trail, Cheryl thinks about the ways she feels ill-equipped, and she wonders whether different parental relationships would have helped her to feel stronger or more confident. Eddie, Cheryl's stepfather, seemed for a time like someone who could provide a paternal influence in her life, so his distancing of himself after Bobbi's death is even more painful. All of the parental figures in Cheryl's life have eventually died or abandoned her, so it is unsurprising that she finds it hard to trust people or believe that she is worthy of love.
Cheryl's disappointment with Eddie is manifested in how he stopped caring for Lady, Bobbi's horse. Bobbi's love of horses suggests that she shared some of the qualities that have led her daughter to the PCT: a connection to nature, a love of freedom, and a desire to live an unconstrained life. Since Cheryl witnessed her mother's suffering during her illness, she finds the suffering of the animal particularly unbearable. The decision to shoot the horse themselves seems somewhat bizarre, but it might reflect the need for closure and control that Cheryl has been struggling with. She never got to be with her mother in her final moments, but she can experience the finality of Lady's death. Not unlike Cheryl's experience on the trail, the reality of Lady's death is uglier and more brutal than she anticipated. Nonetheless, it does seem to bring some measure of peace to both Cheryl and Leif.