During a hometown memorial for his Kentucky-born father, a young man begins an unexpected romance with a too-good-to-be-true stewardess.
After causing a loss of almost one billion dollars in his company, the shoe designer Drew Baylor decides to commit suicide. However, in the exact moment of his act of despair, he receives a phone call from his sister telling him that his beloved father had just died in Elizabethtown, and he should bring him back since his mother had problem with the relatives of his father. He travels in an empty red eye flight and meets the attendant Claire Colburn, who changes his view and perspective of life.
Oregon based Drew Baylor contemplates suicide after his professional world starts to fall apart. A running shoe designer for Mercury Worldwide Shoes owned by the egomaniacal Phil DeVoss, he cost the company close to $1 billion after his latest much hyped running shoe design, the Späsmotica, which was supposed to revolutionize the industry and which just went into mass production and initial distribution, is recalled, the shoe ultimately deemed an utter failure. Drew is fired, with news of the fiasco to hit the public consciousness in a featured article in one week's time. Before he can commit suicide, he learns that his father, Mitch Baylor, has just died of a heart attack while visiting his hometown of Elizabethtown, Kentucky. As the oldest offspring and as his mother, Hollie Baylor, was dependent upon Mitch for everything in life, Drew is assigned to go to Elizabethtown to represent Hollie, his sister Heather Baylor, and his own wishes for Mitch's funeral against Mitch's extended family, who Hollie, Heather and Drew have not seen in years. There is especially bad blood between Hollie and the Baylors because she was the one who stole him away from Elizabethtown to the west coast, and from his Elizabethtown girlfriend Connie to whom he was engaged. Drew plans to go to Elizabethtown to carry out this task before he returns home to continue with his suicide mission. Drew feels overwhelmed in this task as he is seen by the extended Baylor family as the successful one, and he feels he needs to maintain the façade for his mother's sake. To deal with this overwhelming situation, he turns to the one person he feels he can, namely Claire Colburn, the gregarious flight attendant he met on his Louisville inbound flight. Ultimately, Claire may not only help Drew get through the funeral arrangements, but may provide Drew with a different perspective of his life.
After causing the Oregon shoe company he works for to lose hundreds of millions of dollars, Drew Baylor is fired for his mistake, and promptly also dumped by his girlfriend, Ellen. On the verge of suicide, Drew is oddly given a new purpose in life when he is brought back to his family's small Kentucky hometown of Elizabethtown following the death of his father, Mitch, as it falls to him to make sure that his dying wishes are fulfilled. On the way home, Drew meets a flight attendant, Claire Colburn, with whom he falls in love, in a romance that helps his life get back on track...
Hours after a ruinous product debut, suicidal industrial designer Drew Baylor learns of his father's sudden death. As the only son, Drew must travel to their small hometown of Elizabethtown, Kentucky to attend to his father's memorial. On the flight to Kentucky, Drew meets Claire, a quick-witted flight attendant, who helps him navigate the rough waters ahead and proves that amazing things happen when you least expect them.
- 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 things through, 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, Heather 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 Baylors. 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.