Things have been better for Drew Baylor (ORLANDO BLOOM). Not only has he been informed by his boss, Phil DeVoss (ALEC BALDWIN), that his latest athletic shoe design will cost their company $972 million dollars, but his girlfriend Ellen (JESSICA BIEL) had dumped him and when he tries to kill himself, he's interrupted by a phone call.
It's his sister Heather (JUDY GREER) who's called to say that their father Mitch has died of a heart attack in his hometown of Elizabethtown, Kentucky. With Heather and their mom Hollie (SUSAN SARANDON) too distraught to go, it's up to Drew to fly there from Oregon, attend the memorial service and return with his father's remains.
Still reeling from all of the bad news, Drew isn't ready for Claire Colburn (KIRSTEN DUNST), a perky and cheery chatterbox who works as a flight attendant and won't let him be on the otherwise almost empty overnight flight. Armed with her directions and phone number in case he needs anything, Drew sets off from the airport for Elizabethtown.
There, he meets relatives such as his cousin Jessie (PAUL SCHNEIDER), who lets his young son run wild in a hands off sort of parenting approach, and old family friend Bill Banyon (BRUCE McGILL) who Hollie states swindled her husband out of money years ago. Everyone's very welcoming to Drew, but in such mass numbers and with so much attention, they're overwhelming.
Accordingly, and needing someone more like him to talk to, Drew decides to give Claire a call from his room in a hotel already full of attendees for an upcoming wedding. The two instantly bond over the phone, finding kindred spirits in each other. Since she says she has a boyfriend, he doesn't expect much, but sparks eventually fly. As he tries to get to know her better, Drew much figure out his life including how to deal with his previous business fiasco as well as all of his relatives and family friends who don't want Mitch's remains taken back to Oregon.