This chapter explores how hitchhiking—with its promise of free, untethered, and spontaneous mobility—allowed youths of the late sixties and early seventies the ability to maintain a largely nomadic existence while living out the values of the hippie (or freak, as many self-identified) lifestyle. Within the national culture soliciting rides became closely connected to an increasingly politicized counterculture—one that sought to upend the Protestant work ethic and conventional sexual and gender norms. Notably, this radicalized youth culture and its dismissal of traditional values generated resentment among many, creating a deep cultural divide between young people and older, so-called straight Americans. Because of its association with the freak movement, the act of hitchhiking became a key point of confrontation. An increasingly mature regulatory state began cracking down on the practice, in part to reign in the counterculture and women’s liberation movement, but also to promote safer and more uniform traffic behavior. Still, these efforts did little to slow the growing popularity of the practice in the early 1970s.