Milestones is a richly observed, many faceted portrait of those individuals who sought radical solutions to social problems in the United States during the 1960s and 1970s. The film cuts back and forth between six major story lines and more than fifty characters as it scans across a vast American landscape to explore the lifestyles and attitudes of those survivors of the American left who faced both personal and political transitions in the period following the Vietnam War. The filmmakers touch on such subjects as black and Native American rights, on the readjustment experiences of a Vietnam veteran and an ex-convict, on parent-child relations and the family, and on sexual alternatives, communal farming, drugs, and regional politics.