In the summer of 1969, Elliot Tiber (Demetri Martin) divides his time between Greenwich Village and the upstate ramshackle motel, El Monaco, of his Old World parents. When the proposed venue for the upcoming Woodstock concert falls through, Elliot steps in and plays a pivotal role in the generation-defining event by helping organizers secure Max Yasgur's nearby farm for the festival and offering the El Monaco as the home base.