Drew Baylor (Bloom) is an intelligent young man and designer for a shoe company. When his latest design, hyped to be a great accomplishment in his life, has a flaw that will cost the company $972 million to correct, Drew is shamed by his boss (Baldwin) and his coworkers before he is dismissed. Disappointed in his failure, and the subsequent breakup with his girlfriend Ellen (Jessica Biel), he plans an elaborate suicide by taping a butcher knife to an exercise bike, only to be stopped at the last moment by a tearful call from his sister Heather (Judy Greer) that his father died of a heart attack while visiting family in Elizabethtown, Kentucky. Drew volunteers to retrieve the body, following a memorial service when his mother Hollie (Sarandon) refuses to go, following a dispute between her and the rest of the Kentucky Baylors, who consider them "Californian" despite the fact they were in California for a little over a year 27 years before, and instead live in Oregon.
On the flight to Kentucky, Drew meets Claire (Dunst), an optimistic, enthusiastic and kind flight attendant who gives him a seat in first class, due to the plane being empty, so she does not have to travel all the way back to coach. She proves helpful and happy to an otherwise despondent Drew, giving him directions, instructions and tips on getting to his destination before they part ways. When he gets to Elizabethtown, Drew is met with the love of the family, though he is somewhat goaded by being a "California Boy" and he makes the arrangements for a cremation at Hollie's request despite the family's objections. While staying at a hotel, where a wedding reception is being held for the weekend, Drew calls his mother and sister, then his ex-girlfriend as he continues to struggle with his suicidal thoughts. Finally, he calls Claire, who relieves his anxiety and the two of them talk for hours. She impulsively suggests they drive out to meet before she has to depart on a flight to Hawaii that morning and they meet and talk.
Drew comes to grips with his father's death, and while he is visiting his Aunt Dora, his uncle Bill remarks on how his father would look in the suit. Drew realizes that he hadn't given the suit to the mortuary to be cremated, and has second thoughts on the procedure. He rushes out to stop the cremation but is too late and is given his father's ashes. Claire returns from her flight and unexpectedly meets him at the hotel where they become friends with Chuck and Cindy, whose reception is the one being held there. Drew and Claire sleep together, but when she tells him she loves him, he responds with regret that he failed his company and failed at his life, admitting he was contemplating suicide. Claire shrugs it off, saying that it's only money and leaves upset when Drew does not respond.
Hollie and Heather arrive for the service, and Hollie gives an amusing anecdote with her eulogy, likening herself to a comedian, before dancing to their song. Claire arrives, and during a band's presentation of Lynyrd Skynyrd's 1974 song "Free Bird" a prop lights on fire, setting off the sprinkler system. Claire tells Drew to take one final trip with his father, giving him a map and marking special stops to make along the way. Drew follows the map home, spreading his father's ashes at memorable sites until the map gives him a choice; to either follow the map home, or follow new directions. He chooses the latter, which leads him to a small town fair, where he encounters Claire waiting for him. The two kiss and Drew finally realizes what Claire has been telling him all along: life is going to be filled with fierce battles, but through the battles, redemption is found and results in a glorious life.
Claire tells Drew to take one final trip with who?
His father