Plot
Divorcée Helen books a beginners' Appalachian Trail survivalist course. While seeking her brother Duncan to give him keys to housesit, she sees her brother's friend Jake.
Helen's ex Mike calls, reminding her their sixth wedding anniversary would have been today, so she has a flashback. Both Jake and Duncan were at the wedding, disapproving of the clumsy Mike.
Helen pops in to see Gigi, the grandmother who'd raised them, on her drive from Pittsburgh. Staying in the designated Connecticut motel, the next morning the young hiking guide Beckett gives them their trip orientation. Introducing themselves, 40+ Helen discovers she's one of the eldest participants, which fellow older hiker Hugh happily notes. Then she is shocked to see Jake.
Confronting Jake afterward, as he won't leave, Helen suggests they not interact and keep their connection quiet. Shortly after the bus drops the group off at the 50+ mile hike's starting point, Helen immediately gashes her leg. Jake, a doctor and designated EMT, dresses her wound and congratulates her on her divorce.
Soon after, Helen gets scolded for stepping on a log, one of many rules they should have memorised. They learn how to put up a bear hang to protect them and their food. Helen's tentmate Windy is 'crushing on' Jake, but Helen only sees him as immature.
The next morning, Helen asks Jake for help with blisters as she has the wrong footwear and didn't prevent them. Beckett partially blames Mason, the Wall Street hiker, for not being a team player by pushing everyone.
Windy tries to promote positive thinking. Everyone gets to know each other, Hugh sharing that he had been an aspiring actor but now sells insurance. When they are next alone, Helen confronts Jake about his staring and hovering. He says he simply fears her returning to Mike, as he's not good enough for her.
After hiking for ten days, Beckett has them rehike a route, grouped according to speed. He insists Mason go with the slower hikers to promote team-building. Before leaving, Beckett has a fit when he finds Helen's personal goal list, which she had accidentally dropped. No one claims it, but Jake quietly shows he knows, then hands her something to read later.
In Helen's hiking group, they gossip about Jake and Windy, suggesting chemistry, as a quick kiss is mentioned. While everyone else is checking the map, Hugh foolishly plays balance beam on a rotten log. Breaking his leg, as Mason freezes, Helen goes for help.
Helen catches up with the lead group after nightfall, so they decide to go find them at dawn. Sharing a tent with Jake, she tells him about her middle brother Nathan. He drowned when Helen was six, which she felt responsible for. The family unraveled, as their dad, then their mother, left them. They both act jealous: Jake over her accepting Mike's constant messages and Helen over his kiss with Windy, although it was during a game of Truth or Dare.
Early in the morning, they carry Hugh on a makeshift stretcher to an awaiting ambulance three miles away. The next day, they all relax and chat and when dusk falls, Helen seeks out Jake, who is absent. Grateful, he hugs her then explains he inherited a degenerative eye disease so is gradually going blind. It affects him mostly at night and is why he couldn't find his dropped glasses, and also why he'd stopped practicing medicine. They nearly kiss but are interrupted.
The next day, back at the motel, karaoke and other farewell activities are planned, but Helen ducks out after overhearing Jake has someone at home. Driving to Gigi's, she can only think of him. Finally reading the Pablo Neruda poem he'd given her, she realises he has feelings for her. Gigi believes the trip has changed her and she might be in love.
When Duncan comes over, Helen apologizes and vows to be a better sister. He insists she go out with him and Gigi to celebrate a birthday. Jake shows up and they finally kiss, after he confesses he's loved her for years. The movie ends with a montage of Beckett repeatedly addressing many new groups of hikers, his great happiness.
