The film begins with a recall of Mercury Worldwide Shoes' latest product, designed by Drew Baylor (Orlando Bloom). Drew is brought before the head of Mercury, Phil Devoss (Alec Baldwin), who explains to Drew that the company is expected to lose $978 million due to the failure of the shoes that he designed.
After being fired, Drew returns home, where in an act of desperation, takes all his worldly goods to the curb outside his apartment, before rigging a suicide machine from an exercise bike and a kitchen knife. However, before he can go through with his plan, his sister Heather (Judy Greer) calls him, to inform him that their Dad (Tim Devitt) has died from a heart attack while visiting family in Elizabethtown, Kentucky. Drew puts his plans on hold so that he can travel to Elizabethtown to retrieve their Father's body, while Heather contends with their Mother (Susan Sarandon), who responds to this news by learning all sorts of new things, from cooking to tap-dancing.
On the plane flight, Drew meets up with a stewardess named Claire (Kirsten Dunst), who strikes up a conversation with Drew. As she's also from an area near Elizabethtown, Claire ends up drawing out a map for Drew to follow. Drew doesn't follow the map, and almost gets lost, before finding his way to Elizabethtown.
Drew has never met his Father's side of the family until now. He is welcomed with open arms by almost everyone, but finds them apprehensive when he tells of the possibility of cremating his Father. He also meets his cousin Jessie (Paul Schneider), who seems to have little control over his noisy, mischievous son Samson (Maxwell Moss Steen, Reid Thompson Steen). At the same time, the entire Baylor family decides to throw a memorial service for Mitch, in a few days.
While staying in Elizabethtown, Drew checks into a local hotel, which is serving as the site for a raucous wedding for a couple named Chuck (Jed Rees) and Cindy (Emily Rutherfurd). One evening, wanting to speak to someone, he tries calling his sister Heather, his former girlfriend Ellen (Jessica Biel), and Claire. In a roundabout phonecall, Drew finds his sister pleading for help as their Mother won't stop doing things in the wake of her husband's death, Ellen unceremoniously dumps him over the phone, and Claire ends up providing a stimulating conversation. It is here that Drew reveals that originally, he and Mitch were going to try and take a road trip to Elizabethtown some years ago, but this never happened. Claire tells Drew that he should take a road trip on his return trip, and Drew takes this into consideration.
As it turns out, Claire has returned from her duties with the airline, and is 45 minutes away. As Drew has been talking to her into the early morning hours, the two decide to meet up to watch the sunrise, before going their separate ways.
However, Claire shortly re-enters Drew's life. Talking through things, Drew decides to remain firm on the cremation of his Father, and Claire helps him pick out an Urn for his Father, Mitch. She also provides him with a videotape that ends up quelling Samson's noisy tantrums. However, at the last minute, Drew decides to not have his Father cremated, but it's too late. Afterwards, Drew and Claire share an intimate evening together, before Drew confesses to Claire about his 'failure' with Mercury Shoes. Claire simply tells Drew to stop feeling sorry for himself, and that as a creative person, he should just keep on going.
Finally, the day of Mitch's memorial service is at hand. At the last minute, Judy and their Mother (Hollie) have decided to attend. A number of Mitch's family and friends speak, before Hollie stands up and introduces herself. After giving a humorous anecdote about life as a widow, she then does an interpretive tap-dance to her husband's memory, much to the delight of the Baylor's. Drew steps out for a moment, and finds himself face-to-face with Claire, who has brought a present for him: a kit for his road trip back home to Oregon. However, before they can say anymore, Drew's cousin Jessie takes to the stage with his band, playing the song 'Freebird' in tribute to Mitch. However, a papier-mache bird ends up catching fire and setting off the sprinkler systems, sending everyone scrambling from the meeting place.
The next day, a funeral is held in the place of Mitch's burial plot, with mementos of Mitch put in the casket. Once services end, Drew begins his road trip, following the CD's and instructions that Claire has outlined. Along the way, Drew sprinkles Mitch's ashes at various locations. Finally, Claire's instructions lead him to "The World's Second Largest Farmer's Market." After following clues in her notes and at various stalls at the market, her instructions give Drew a choice- 1) He can get back in the car, and continue his journey, or 2) He can look for a girl with a red hat. Drew chooses the second choice, and finds Claire at the market.
