Counterculture is a major cultural and political movement that affected all major spheres of the American mainstream, and this paper deals with its feminist implications. Young hippies, or counterculturers, sprung out of the 1950s mainstream society, rejecting the societal roles and lifestyles of their parents, and reviving egalitarian values and redefining the established gender roles. Whilst many would argue feminism of the 1960s bypassed Counterculture, and would only associate it with the New Left, I would argue feminism was an integral part of the hippie society. Along with the sexual revolution, Counterculture redefined the sexual roles of women, and provided young women with a new alternate lifestyle. This research aims to portray how the Counterculture influenced feminism, and vice versa, and to display the shift in the paradigm that occurred in the 1960s, with regards to women and how they are represented in society and the mainstream. Counterculture feminism is explored through 3 distinctly feminist literary works, The Group, The Bell Jar, and I’m With the Band. Whilst the previous two deal with ‘the problem with no name’ that heavily affected women in pre-Counterculture mainstream society, I’m With the Band portrays a uniquely countercultural lifestyle of a groupie that embraced her own autonomy and sexuality.