At the end of the fifteenth century, Hieronymus Bosch provided the foremost expression of the strict religious piety embodied by the Devotio Moderna and the impending embrace of secular humanism. As a result, Bosch's seemingly complex images provided viewers with positive messages concerning the journey of life through the use of binary symbolism. He utilized the pilgrimage motif as a guide throughout his paintings and in relation to the liminal spaces surrounding his works. This article will examine his important triptych, The Haywain, (c.1495-1516) as an example of spiritual paths taken simultaneously by both religious and contemporary figures, along with the viewers themselves. The underlying theme of Christ's Ascension in The Haywain plays out in an interwoven assortment of journeys, identified by characteristic northern and medieval Christian iconography. Christ's final journey acts as the ultimate goal and the paradigm for both the pilgrim within the triptych and the viewer. Evidence of processional celebrations mimicking pilgrimages reveals that the motifs in Bosch's works were located throughout his visual culture. Finally, an investigation of Bosch's 1505 triptych The Temptation of St. Anthony reveals that Bosch remains consistent in his use of the pilgrimage theme. Bosch worked within the context of the visual and textual culture of the Netherlandish city of ‘s-Hertogenbosch, and despite his creative style, was understood among his contemporaries as a messenger of positive piety.