Cheryl continues on with Stacy and Trina, covering the fifty miles to Stover Camp, where they part ways to hitchhike. As Cheryl tries to catch a ride, she meets a man named Jimmy Carter who tells her that he writes about the "hobo life" and asks her questions about her journey. Despite being annoyed, Cheryl is pleased when he gives her a can of beer and some food. Cheryl ends up being picked up by a woman named Lou and two men named Spider and Dave, who are brothers. Lou is going to be married to Dave soon, and she tells Cheryl that, five years ago, she lost her young son in a car accident. They drive Cheryl to Old Station, where she reunites with Stacy and Trina. Cheryl is pleased to hear that a new water tanker has recently been installed about fifteen miles away, which should alleviate the need for her to carry large amounts of water on the trail. Trina and Stacy set off, but Cheryl stays an extra day, feeling more confident now that her pace has improved. Cheryl thinks about the idea of becoming a writer and impulsively phones Paul, telling him about her adventures on the trail.
The next morning, Cheryl resumes her hike, facing intense heat as she hikes over Hat Creek rim. The heat leads her to quickly deplete her water supply, so she is relieved when she encounters the water tank where she is scheduled to refill. However, she is dismayed to realize that the water tank is empty. Desperate, she heads towards a reservoir known to have water of questionable quality. Cheryl purifies the water from the reservoir and drinks it, waking up to tiny frogs crawling all over her. She sets off the next day in a weakened condition and doesn't make much progress. She detours off the trail to a general store in a town called Cassel, where she chats with a fellow hiker named Rex. He tells her that if her boots are too small, she can ask the company to send her new ones. The next day, Cheryl hikes the rest of the way to Mc-Arthur Burney Falls Memorial State Park, where she picks up her resupply box and phones to arrange to have new boots sent to her.
Cheryl is initially happy with her plan, but she becomes concerned as she waits for the boots to arrive since the delay risks affecting her progress on the trail. When she learns it will be five days before she can have the boots, she asks them to be sent to her next stop, resigning herself to hiking the next stretch in her ill-fitting boots. Frustrated, Cheryl thinks about a prediction an astrologer once made about her needing to fight a battle in order to heal a wound left by her father. As Cheryl walks the next day, she thinks about the history of the trail and the dedication of those who worked to make it possible for her to be hiking it.
As she approaches Castle Crags, Cheryl sits down to rest on the edge of a slope and accidentally knocks one of her boots off the edge. She now has to continue in only her sandals. Continuing on, she recalls how, before she began her hike, she had driven to see Eddie and visit her mother's grave on the rural property. She arrived during a party and was greeted by her brother, only to be upset by seeing the old kitchen table being carved on by party guests. She and Leif reminisced together, reflecting on what her life might look like after she finishes hiking the trail. They also visited an abandoned house nearby that they used to sneak into as children.
On the trail, Cheryl continues her hike, concerned because she is feeling disoriented and lost. Her sandals have also fallen apart, so she is now hiking in foot coverings from makeshift duct tape. Finally arriving at Castle Crag, Cheryl picks up her resupply box, her new boots, and letters that have been forwarded to her during her time hiking. She also reunites with some of the hikers she had met earlier on the trail, and they all camp together that night. The next day, Cheryl is annoyed to find that her new boots still hurt her feet.
Because of her difficult experience on the trail, Cheryl is eager to take a few days off and spend them at the Rainbow Gathering, a festival. However, the hikers can't locate the Rainbow Gathering, even though they come across other hippies looking for it as well. She crosses paths with a woman named Vera who is hiking with a small boy named Kyle, but she is mostly alone. As Cheryl approaches the border of California and Oregon after more than 50 days on the trail, she realizes that she is finally feeling stronger and more confident.
Cheryl's boots have been causing her pain and suffering since the start of her hike. She has been feeling frustrated, but she is also unable to come up with any ideas about how to resolve this problem. To someone else, the solution is obvious. Cheryl's realization that she can order new boots reflects why it can be hard to change one's life, and why she has spent four years stuck in something of a rut. While the trail has taught her to be self-reliant, it has also shown her that other people can be incredibly helpful. However, her confidence that she will soon have new and better boots leads her to an exaggerated expectation of happiness and comfort. Cheryl becomes even more frustrated when her boots are delayed, she loses one of the originals, and she ends up with a pair that still hurt her feet. The whole experience exemplifies, once again, the balance of surrender and agency that she has to grapple with.
Nonetheless, Cheryl's confidence in herself is steadily improving. This optimism about her time on the trail allows her to contemplate what she might want her life to look like after she finishes her hike. Cheryl has become intrigued with the idea of becoming a writer, which makes sense given her clear love of literature. There are also more powerful psychological factors at play here: for Cheryl to contemplate a career as a writer, she needs a sense that she has a voice and stories worth telling. Before beginning her hike, Cheryl felt totally lost and aimless. Now, she can start to see things about who she is and what she has to offer to the world. Cheryl's tentative career plans are a sign that her journey is helping her to reclaim her sense of self.
Cheryl's optimistic plans are also foiled when it comes to joining the Rainbow Gathering. Cheryl has been reliant on socialization from fellow hikers and her stops in towns, but she longs for a festive gathering and a sense of community. The inability to find the gathering functions as a kind of playful extension of the theme of lostness that has been haunting Cheryl throughout the memoir. She struggles to find a direction in life, and she struggles to maintain a sense of direction on the trail. What is powerful in this case is the realization that others are just as lost as she is, and perhaps not handling it so well. The exaggerated helplessness of the hippies trying to find their way to the gathering is comical in contrast to what Cheryl and the other PCT hikers have to deal with on a daily basis. Cheryl will always be able to look back and see how much stronger her hike has made her.