Recent scholarship has challenged the still-powerful claim that long-distance pilgrimage and the journey to Jerusalem dramatically declined in number and significance in the sixteenth century. This article seeks to explore the different ways in which pilgrimage was embedded in the culture of the period. We interpret pilgrimage as a field of shared cross-confessional practices, representational conventions, and contestation. The paper presents a series of interlinked case studies, based on printed sources, correspondence, family archives, and material evidence. Together they demonstrate that early modern pilgrimage perpetuated medieval practices and yet was in constant dialogue with contemporary, post-Reformation religious and intellectual trends.