Plot
Divorcée Helen books a beginners' Appalachian Trail survivalist course. While at a party looking for her brother, Duncan, to give him keys to housesit, she speaks to her brother's friend Jake.
When Helen's ex Mike calls, reminding her their sixth wedding anniversary would have been today, she has a flashback. Both Jake and Duncan were at the wedding, disapproving of the very awkward Mike.
Northbound 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 guide Beckett gives them an overview of the hiking trip. They introduce themselves and 40ish Helen discovers she's one of the eldest participants, which fellow older hiker Hugh happily points out. Then she is shocked to see Jake appear and introduce himself.
Confronting Jake afterward, as he won't leave, Helen tells him to not interact with her 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 on a rock. Jake, a doctor and therefore the designated EMT, dresses her wound and congratulates her on her divorce.
After a short time, Helen gets scolded for stepping on a log, one of many rules they should have learned beforehand. Beckett shows them 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 didn't bring the correct footwear and didn't prevent it. Beckett casts some of the blame on Mason, the Wall Street hiker, for not being a team player and 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 again, 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.
As they have been 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 had fallen from her pocket. No one fesses up to owning it. Jake, who knows it was hers, quietly calls her out for it, then hands her something to read later.
In Helen's hiking group, they gossip about Jake and Windy, suggesting there is chemistry. A quick kiss is mentioned. While everyone else is checking the map, Hugh foolishly plays balance beam with a rotten log. Severely damaging his leg, as Mason freezes up, Helen steps up and offers to go for help.
Helen explains what happened when she reaches the lead group after nightfall, and they decide to go find them at dawn. Sharing a tent with Jake, she tells him her middle brother Nathan had drowned when she was six. Helen felt responsible, and the family unraveled with first their dad, then their mother, leaving 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.
Waking at dawn, Helen takes the other three to Hugh and company. She and the men carry him 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 has departed from the group in the woods. Grateful, he hugs her then explains he inherited a degenerative eye disease causing him to slowly lose his sight. It currently affects him most at night and is the reason why he couldn't find the glasses he'd dropped, and also why he'd stopped practicing medicine. They nearly kiss but are interrupted.
The next day they head for the bus, which takes them back to the motel. Meant to participate in karaoke and other farewell activities, Helen ducks out after overhearing that Jake has someone at home. Driving to Gigi's, she can only think of him. Finally reading what he had written her (a poem by Pablo Neruda), she discovers he has feelings for her. Gigi sees the trip has changed her and thinks she might be in love.
Duncan comes over, and Helen apologizes for how she's treated him over the years and vows to be a better sister. Duncan insists Helen 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 repeating "Okay, people", indicating many new groups of hikers, which he finds his happiness in.
