When searching the 2nd Largest Farmer's Market in the World for a woman in a red hat, Drew walks past a signpost with arrows pointing to "Success" and "Failure". He takes the "Failure" route to reach Claire.
Cameron Crowe had written the role of Drew Baylor with Orlando Bloom in mind. When Crowe originally offered Bloom the part, Bloom was unable to take it due to scheduling conflicts with Kingdom of Heaven (2005). Crowe then cast Ashton Kutcher in the part but later felt that Kutcher and co-star Kirsten Dunst had no chemistry and decided to let him go. Crowe then pushed his January 2004 start shoot date back to July 2004 for a summer shoot. Many young actors that included Seann William Scott, James Franco, Colin Hanks and Chris Evans auditioned for the part of Drew. Scott was seriously considered and nearly nabbed the part but Crowe pushed to get Bloom instead. When Bloom was able to work the film into his schedule, Crowe cast him in the part.
Cameron Crowe's first choice for the part of Claire Colburn was Kirsten Dunst. Dunst wanted the part very much but had already signed for The Village (2004). Evan Rachel Wood (who was apparently too young) was then under consideration for the part but Dunst dropped out of The Village (2004) at the last moment to audition for the part and won it. Judy Greer, however, appeared in both "The Village" and "Elizabethtown".
The Claire Colburn character in this movie was the reason for "The A.V. Club" columnist Nathan Rabin's coinage of the term "The Manic Pixie Dream Girl," which later entered into common usage in movie writing. Rabin's definition of the term, which first appeared in a 2007 article titled "My Year Of Flops/The Bataan Death March of Whimsy Case File #1: Elizabethtown," was: "The Manic Pixie Dream Girl exists solely in the fevered imaginations of sensitive writer-directors to teach broodingly soulful young men to embrace life and its infinite mysteries and adventures. The Manic Pixie Dream Girl is an all-or-nothing-proposition. Audiences either want to marry her instantly (despite The Manic Pixie Dream Girl being, you know, a fictional character) or they want to commit grievous bodily harm against them and their immediate family. As for me, well, let's just say I'm not going to propose to Dunst's psychotically chipper waitress in the sky any time soon...(see Natalie Portman in Garden State (2004) for another prime example)."
While shooting a scene in a cemetery with actors Orlando Bloom and Kirsten Dunst, filming was interrupted due to an unexpected rain storm. Cameron Crowe suggested they shoot the scene anyway because it looked more beautiful and natural.
Loudon Wainwright III plays Uncle Dale in the film, and on one of Claire's play list in the Road trip scrapbook, you can see "Oh What a World" by Rufus Wainwright listed. Rufus is Loudon Wainwright's son.
Southern cooking queen Paula Deen of Food Network fame made her big screen debut in this movie as Aunt Dora. Deen's character is of course is depicted doing plenty of cooking. A Food Network special, Paula Goes Hollywood, aired in conjunction with this film's premiere.
A scene was shot in the John Wayne Airport in Orange County. It was the first time since the terrorist attacks on the USA of 11 September 2001 that a film has shot there. The crew was given only one night to shoot.
When Drew arrives in Elizabethtown, you're actually seeing downtown Versailles, KY. Shops on Main Street redressed their windows to accommodate filming.The funeral home "Clark Funeral Home" is also located in Versailles, KY.
When Drew is driving through Louisville on his way to Elizabethtown from the airport, he's actually going in the wrong direction. Cameron Crowe did this to give the scene more character. The actual route is pretty remote without much scenery.
The fictitious Mercury shoe company is headed by a guy named "Phil DeVoss", it is from Oregon, and it is an athletic shoe company. Nike, an athletic shoe company, was co-founded in Oregon by Phil Knight who later became Nike's CEO and Chairman of the Board.