As with virtually all writers of the Beat Generation, the attitude of the literary-critical establishment towards Jack Kerouac’s works has been turbulent. Dubbed “a Neanderthal with a typewriter,” and having his oeuvre panned (most notably by Harold Bloom) as having “no literary value whatsoever” or dismissed for moral reasons, Kerouac seems to have little to offer contemporary audiences and scholars being categorized as quasi-picaresque epigone of the romantic tradition, celebrating immature dropout attitude and a life of excess mingled with a shallow understanding of Eastern religions. Whereas I concur with the claim that Kerouac’s works do display some deficiencies of style, my essay argues for a more constructive reading of the motive of journey explored in his central novels (particularly in On the Road, Dharma Bums and Visions of Cody), as I would like to overview some striking similarities between the experiences of Kerouac’s characters and the primal, ritualistic traverses of shaman-like figures in early cultures. On such a reading (inspired chiefly by Mircea Eliade and Joseph Campbell’s Hero’s Journey), Kerouac’s hero’s journeys appear to be taking place both at the physical, spiritual and psychic level and are attempts at self-healing, pacifying, maturation and reconciliation with society. They are not then, straightforward rejection and escape, but a temporary, painful strategy, whose final aim is to return to society as a transformed individual, though as the development of the journey motif across his oeuvre demonstrates, this attempt at transformation and reconciliation need not be entirely successful.