This article examines representations of the road in the work of independent Florida-born film director Kelly Reichardt. Reading Reichardt's so-called Oregon trilogy, Old Joy (2006), Wendy and Lucy (2008), and Meek's Cutoff (2010), alongside radical anti-freeway and anti-automobile movements from the Pacific Northwest, I argue that Reichardt's films offer critical engagements with the subject of the American road, interrogating the freedom and emancipation from social constraint it purportedly offers.