Divorcée Helen decides to embark on a beginner's Appalachian Trail survivalist course as a fresh start in life. Just before her departure, she tries to locate her brother Duncan but instead encounters his close friend Jake, who she asks to keep an eye on her home while she's away.
As she prepares for the course, Helen receives a phone call from her ex-husband Mike, who reminds her that it would have been their sixth wedding anniversary. This prompts a wave of nostalgia as she recalls their wedding day, where both Jake and Duncan were present, silently disapproving of Mike's awkwardness.
On her journey from Pittsburgh, Helen makes a stop to visit Gigi, the grandmother who raised them. After checking into a motel in Connecticut, Helen meets the young guide Beckett who outlines the hiking adventure ahead. To her surprise, she finds she's one of the oldest participants, and Hugh is quick to point this out. The situation becomes even more complicated when she discovers that Jake is also part of the group.
Faced with the unexpected presence of Jake, Helen confronts him about their past, insisting that he keeps their history under wraps. Shortly thereafter, their adventure kicks off with a hike, during which Helen injures her leg on a rock. Luckily, Jake, being a doctor and the assigned EMT, takes care of her injury and awkwardly wishes her well on her divorce.
As they navigate the challenges of the AT, Helen's tendency to violate the group's rules draws criticism, particularly from Beckett. Meanwhile, her tent companion Windy develops a crush on Jake, but Helen sees him as too immature for her taste. Seeking assistance for her blisters, Helen asks Jake for help, revealing her struggles with inadequate footwear.
Throughout the hike, they all share their backgrounds, with Hugh mentioning his dreams of becoming an actor before he settled for a career in insurance. Once again, Helen has an honest dialogue with Jake, who expresses concern over her reconnecting with Mike, whom he feels doesn't deserve her.
After ten days on the trail, Beckett decides they should hike a path again, emphasizing teamwork, which leads to tensions with Mason from Wall Street who is reluctant to support his fellow hikers. Helen finds herself on the verge of losing everything when she accidentally drops her goal list, but instead of fessing up, Jake quietly brings it to her attention later.
Rumors swirl among the group about a spark between Jake and Windy, and an accidental kiss is brought to light, only adding to Helen's frustration. In a dramatic twist, an injury leaves Hugh in need of assistance, prompting Helen to rush to the lead group under the cover of darkness. After recounting the incident, they all agree to go back at dawn, and Helen shares a vulnerable moment with Jake about her traumatic childhood, revealing that her family's dysfunction stems from her brother Nathan's drowning when she was just six.
As tensions rise, jealousy brews between Helen and Jake over each other's unaddressed feelings for others. After successfully rescuing Hugh, the group returns to their motel, where emotions run high, leading Helen to seek out Jake alone for a heartfelt conversation in the woods. Hearing about his inherited eye disease that jeopardizes his career as a doctor makes her grateful, but their moment almost turns into a kiss before being tragically interrupted.
With another day gone, the group prepares to leave, ready for the farewell festivities. Yet, Helen panics upon learning that Jake has someone waiting for him back home, prompting her to slip away. As she drives back to Gigi’s, she’s unable to shake thoughts of him. Captivated by a poem (by Pablo Neruda) that he left for her to read later, she realizes that Jake reciprocates her feelings.
Upon returning home, Helen contemplates her changed perspective and the relationships she's mended, especially with Duncan, with whom she shares a heartfelt apology for her past behavior. When Jake unexpectedly arrives to see her, they embrace in a passionate kiss, confirming that their journey together has sparked a newfound love between them.
