Numerous countercultures and alternative ways of life emerged not merely in the 1960s, but also throughout the history of the United States. This work zeroes in upon one of the most significant ones, the hippie counterculture. After dealing with the etymology of the word “hippie,” tentative definitions of both the hippie phenomenon and of the word “counterculture” are given, with the conclusion that hippies never formally united into a mass movement, and hence the word “movement” is a misnomer. Moreover, the Beat generation, as the antecedent of the hippie counterculture, and its two major representatives, Jack Kerouac and Allen Ginsberg, are mentioned along with a brief discussion of the poem called “Howl” and the novel called On the Road, illustrating that they paved the way for the hippies. The paper then proceeds to expound upon the similarities and differences between the Beat generation and the hippie counterculture. The hippies’ prevailing philosophies are also limned, more precisely, the idea of love, arationality, the hippies’ withdrawal from established institutions, and the motto “turn on, tune in, drop out.” The experimentation with creating alternative microsocieties, most notably in Haight-Ashbury, segues into hippie communes and the ethics of the trinity—sex, dope, and rock and roll. Additionally, aside from proposing that Woodstock can be construed as the apotheosis of the hippie phenomenon, the counterculture’s multitudinous legacies are also touched upon. The hippies’ quixotic endeavor to bring about social change by establishing experimental, alternative communities—and thus implicitly setting an example for the rest of society—was infeasible to materialize for a variety of reasons: the hippie phenomenon was disorganized, amorphous, arational, and present-focused; furthermore, the hippies did not have any leadership or a well-defined plan.