Elizabethtown
Though not inherently a "women's" roadfilm, I would consider Elizabethtown to be my favorite. Released in 2005 by director Cameron Crowe, Elizabethtown details the journey of Drew Baylor as his life is turned upside down in a matter of days. I am particularly fond of the style the show is written in - at times it is unclear whether the audience should be laughing or crying. Drew's father dies, but he manages to find an ecctrinc lover, take is first road-trip, and discover who he really is (all in 123 minutes!) The most poignent moment of the entire film, for me, is when Drew embarks on his journey from Kentucky to Oregan with his father's ashes in tow. He is able to make peace with his father, whom he had been neglecting for several years while he was becoming a successful businessman. Drew selects certian destinations where he sprinkles some of his father.
I believe Elizabethtown is so alluring, and the perfect roadfilm, because it has a storyline that is easily relateable. Everyone hits bottom at some point, but Drew slowly accepts his failures and moves forward in his life, a lesson that any viewer can benefit from.