Cheryl crosses the border from California into Oregon, feeling triumphant. She is eager to arrive in Ashland because she has put additional money in the box she will pick up there, along with regular clothes. However, when she arrives, she is dismayed to find that the box is not there. A strange atmosphere also hangs over the town since the death of Jerry Garcia has just been announced. Cheryl is invited a number of times to gatherings to celebrate his life, but she is focused on retrieving her box. Once she has it, she checks into a hostel with fellow hiker Stacy and Stacy's friend Dee. After resting and eating, they decide to go to the Grateful Dead memorial gathering, where Cheryl meets a man named Jonathan. He invites her to come back to the club the next night to join him.
Cheryl and Jonathan listen to music at the club and make plans for her to see his home later that night. She steps outside while waiting for him to finish working, and she meets a man named Clyde, who is living in his truck. She gets into the truck and passes some time with Clyde, who offers her chewable opium. After a while, Cheryl rejoins Jonathan and they drive to the farm where he is living and working. He and Cheryl talk, kiss, and finally go into his tent, where Cheryl is startled to find that he doesn't have any condoms; she left her own back at the hostel because she feared Jonathan might find her unattractive, and she wanted to resist the temptation to sleep with him. Nonetheless, Cheryl spends the night, and the next day, she and Jonathan go to the beach. Cheryl slips off by herself to write Paul's name in the sand, knowing it will be the last time she commemorates him this way. Later, Cheryl and Jonathan make love on the beach before returning to town. The next day, Cheryl resumes her hike, headed towards Crater Lake National Park.
As Cheryl hikes through Oregon, she notices changes in the terrain and temperature. On August 18, her mother's birthday, she thinks about how her mother would have been turning fifty. She recalls her mother's personality and the decision to cremate her. While most of her mother's ashes had been spread on their property in Minnesota, Cheryl had consumed a handful of them. Cheryl also reflects on how, when she was pregnant, her projected due date was the week of her mother's death.
At Shelter Cove Resort, Cheryl picks up another supply box and meets a group of hikers who have been walking just behind her on the trail. They are three handsome young men, whom she nicknames the Young Bucks. They push past Cheryl on the trail, maintaining a faster pace, and she continues through Oregon alone. One day, on a detour from the PCT, she meets two hunters who ask her for water. She offers to let them use her filter to clean pond water, but they end up breaking it. Growing increasingly uncomfortable, Cheryl lies and says she plans to hike on before setting up camp, and the men leave. A few minutes later, they come back and are angry when it becomes clear that she lied about her plan to move on. They eventually leave, but Cheryl is so unsettled that she packs up all her things and starts walking again.
In Olallie Lake, Cheryl retrieves another box and reunites with the Three Bucks. The three of them camp together before being offered a space in a cabin at the resort. Cheryl is also joined by her friend, Lisa, who has driven out from Portland. Before she leaves Olallie Lake, Cheryl also runs into Doug. They agree to hike together for a stretch, although Cheryl wants to finish her hike alone. About fifty miles away from the Bridge of the Gods, Cheryl breaks off alone. Early on a Friday morning, she walks into the town of Cascade Locks, located on the Oregon side of the Bridge, which spans the Columbia River and marks the border between Washington and Oregon. Cheryl pauses to savor the moment, knowing she is only a short distance from Portland, where she plans to stay indefinitely. A man offers to drive her, but she declines, wanting to reflect. Cheryl does not yet know that her future will involve a happy marriage and two children, including a daughter whom she will name after her mother. She does know that her experience on the trail has changed her forever.
After so many weeks on the trail, Cheryl can't wait to enjoy time in a social and festive atmosphere in Ashland. Simple things like music, wine, and pretty lingerie are now treasures that she appreciates on an entirely new level. Cheryl is also eager to reclaim a flirtatious and sexual side of her identity. Because sexuality was something she was using as a coping tool, she needed to distance herself from it during her time on the trail. She has not engaged in any sort of flirtation with any of the hikers she encountered, even though she felt attracted to some of them. However, the memoir makes it clear that the point is not for Cheryl to cut herself off from sexuality forever. Her encounter with Jonathan is part of her healing process because it shows her that is possible to experience pleasure and affection while understanding that a relationship is temporary. Reclaiming her body's capacity for pleasure is just as crucial a way for her to come back to herself as experiencing her body's capacity to endure pain. As Shelly Sanders notes, "her self-doubt and confidence are at once wrapped up in what her body can and will do, without her ordering it to do so" (pg. 20).
While her encounter with Jonathan shows Cheryl the power and beauty of her sexuality and femininity, those same qualities put her at risk in other contexts. While Cheryl felt nervous being a woman hiking alone when she started her journey, she mostly encounters people who want to be kind and helpful. As a result, she becomes more relaxed and trusting. Even though the two hunters she encounters in Oregon make her feel uneasy, Cheryl tries to be helpful. She wants to repay the kindness that others have shown her, especially now that she is the person who has more knowledge and tools to navigate the wilderness. Still, it becomes clear that Cheryl should have trusted her instincts, for the men do indeed pose a threat to her. Although she escapes without incident, it is a cruel irony that despite bears, rockslides, blazing heat, and other natural dangers, the moment where Cheryl is in most immediate danger is because of other humans.
The anniversary of Bobbi's birthday marks a moment of closure and healing for Cheryl. She will never stop missing her mother, but Cheryl is beginning to be more attuned to the natural rhythms of life, death, and regeneration. Her time on the trail has shown her how everything in nature is temporary, but also how it all plays a role in a bigger cycle. She has also seen for herself how all events are moving individuals towards other things. These cycles of regeneration come up in reference to how Cheryl's due date roughly coincided with her mother's birthday. Although this wasn't the moment for her to continue the pregnancy, this coincidence hints at how Cheryl's future children will someday carry on her mother's legacy. Cheryl's decision to consume some of her mother's ashes also seals the unbreakable bond between mother and daughter. Cheryl has literally been carrying her mother with her through her entire journey, and she will continue to do so.
Cheryl's peak moment of liberation and release comes when she finally arrives at the Bridge of the Gods. She has achieved her goal, no matter what she had to endure along the way. She doesn't know what lies ahead, but she feels confident and capable. What her experience on the trail has really given Cheryl is a feeling of hope. The reveal that she will go on to find a loving partner and have children provides a sense of totality and closure to a story extending beyond her hike. It has the effect of showing Cheryl taking up her place in the circle of life and finally feeling able to live up to her mother's memory. Some critics have suggested that including the information about Cheryl's marriage and motherhood counterbalances what is otherwise a narrative focused on independence and rebelling against gender norms; for example, Amy Bowen describes this ending as "a narrative that ultimately reinforces traditional values, where a hike in the woods only makes Strayed more prepared to fulfill domestic responsibilities." However, given how personal the memoir has been, it seems fitting that Strayed offers readers a final perspective on the person she has become.