The bulk of world literature comprises stories of tangible and symbolic quests and American literature is no exception to this general rule. The quest narrative dominates the American literary landscape and, on the surface, is founded on its history as a nation of immigrants seeking, above all, religious freedom. It would have been facile to state that this quest is for the American Dream, and it would have been just as easy to define this modern Dream as social equality and economic opportunity, or vice versa. After all, a prime purpose of the Mayflower project was to become free of medieval Europe’s pomp and show, most importantly in religious practices. However, the ubiquity of ancient symbols in the American quest narrative intrigued me. These symbols indicated hidden meanings that went beyond materialistic realization of America’s constitutional ideals. Exploration of the deeper meanings of quest narratives in modern America required plumbing symbolic depths. The vortex motif helped to go far beneath the surface meaning of the symbols encountered. This quest was both a vertical plunge and a horizontal journey towards a specific goal. Fascinatingly, the quest in the texts analyzed almost invariably ended at a destination that turned out to be its starting point. The hermeneutic cycle helped to explain the circularity of the quest. This study, therefore, set out to explore the nature of the American quest, to sift through the symbols dotting the literary terrain, to encounter a key symbol, to explore its religious content, and to fathom the significance of this symbol in modern American literature. A brief survey of modern American literature proved the presence of quest stories in almost all genres, from science fiction to the American literary canon. In many American narratives, obsession with apocalypse also combined well with the quest theme to make for great story telling. Importantly, they easily reincarnate as cinematic script. Apocalypse has riveted American attention after 9/11 but it also prevailed during the 20th century and earlier American literature produced along modern lines. Quests to survive and flourish invite inclusion of marginal voices, presenting equality of opportunity for blacks, women, the old and otherwise infirm, so essential to American narratives. The quest aspires to assume metaphysical properties. Its goal is an elusive symbol. Powerful symbols contain coded messages dating from ancient religions. In modern narratives they shed their religiosity. However, cult following reestablishes the symbol’s spiritual status. They embody eternal Truth. The Holy Grail exemplifies such powerful symbols. The grail icon is so prevalent in American society that most of its canonical writers are compelled to weave tales around the grail. This study suggests that American society has Americanized the grail, and to understand the United States one must also grasp the manifold meanings of its Holy Grail – there being no better place to start than traverse the modern American literary landscape.