The film kicks off with a glimpse into the troubles surrounding Mercury Worldwide Shoes and its latest product, crafted by Drew Baylor. He faces the ire of the company's head, Phil Devoss (Alec Baldwin), who reveals a staggering projected loss of $978 million due to Drew's failed design. Following his dismissal, Drew, in a moment of despair, clears out his apartment, placing all his possessions on the curb. In a misguided attempt on his life, he rigs a suicide machine using an exercise bicycle and a kitchen knife. However, just as he's about to go through with his plan, a phone call from his sister, Heather (Judy Greer), interrupts him with devastating news: their father has passed away from a heart attack while visiting family in Elizabethtown, Kentucky.
Drew promptly shifts his focus, preparing to travel to Elizabethtown to retrieve his father's body. Meanwhile, Heather struggles to manage their mother, Hollie, who is channeling her grief into learning new skills like cooking and tap dancing. On the plane, Drew meets a friendly stewardess named Claire, who also hails from a town nearby. She offers him a hand-drawn map to guide him, but Drew ends up getting lost anyway, before finally reaching Elizabethtown.
Upon arrival, Drew is warmly embraced by his father’s family, though they express concern about the idea of cremating his father. He also encounters his cousin Jessie (Paul Schneider), who grapples with his rambunctious son, Samson (Maxwell Moss Steen, Reid Thompson Steen). The Baylor family intends to hold a memorial service for Mitch in the upcoming days.
During his stay, Drew checks into a local hotel, bustling with the excitement of a wedding happening nearby. As loneliness creeps in, he attempts to reach out to his sister, ex-girlfriend, and Claire. In this round of phone calls, he learns about his mother’s incessant activities, hears an abrupt breakup, and continues a thoughtful conversation with Claire. Drew shares a poignant memory of a planned road trip to Elizabethtown with his father that never materialized, prompting Claire to suggest he take a road trip back.
As fate would have it, Claire returns to the area, only 45 minutes away. After a night of deep conversation, they decide to meet up at sunrise, savoring a fleeting moment together. Claire soon becomes more involved in Drew's life, encouraging him to pick out an urn for his father and providing him with a video that pacifies Samson's loud outbursts. In a last-minute decision, Drew ultimately opts against cremation, but he realizes it's too late for that choice.
The day of Mitch's memorial service arrives, attended by their mother and Heather, who briefly appear amidst various heartfelt speeches. In a surprising turn, Hollie shares an amusing story about widowhood, culminating in an interpretative tap dance honoring her husband, much to the delight of the attendees. Stepping outside for a breather, Drew encounters Claire, who has brought him a road trip kit. Just as their conversation takes a deeper turn, Drew's cousin Jessie performs a rendition of 'Freebird,' leading to chaos as a papier-mâché bird bursts into flames, prompting a swift evacuation.
The following day, a funeral takes place, during which mementos of Mitch are placed into the casket. Once the services conclude, Drew embarks on the road trip, guided by the playlists and instructions provided by Claire. As he travels, he scatters his father's ashes at significant spots. Intrigued by her notes, Drew eventually finds himself at "The World's Second Largest Farmer's Market." Following her hints, he faces a choice—either to resume his journey or to locate a girl wearing a red hat. Opting for the latter, he discovers Claire waiting for him at the market, leading to the promise of new beginnings.
