In this dissertation, I turn to three major pilgrim accounts from fourteenth- and fifteenth-century England (and the nearby continent) in order to explore how these pilgrims situated themselves spatially in order to access times outside their own moment. Each of these texts – William Wey's Itineraries, The Book of Margery Kempe, and The Book of John Mandeville – depicts adventures and voyages to myriad locations in and beyond medieval Europe, and while all these writers hailed (or purported to hail) from England, their remarkable accounts display a diverse range of beliefs about and attitudes toward temporality, spatiality, and religious experience. It should of course come as no surprise that accounts composed over two centuries may differ in their interests, goals, and source material, but nevertheless in each narrative, Jerusalem and the Holy Land writ-large seems to act as the testing ground for each author's theories on and beliefs about their place in time and their access to the past and future. Ultimately, this dissertation explores how these late-medieval pilgrimage accounts invite and exploit the paradoxes that inhere in temporality in order to imagine and create new ways of being in and navigating time.