This dissertation examines the historical and artistic circumstances behind the emergence in late medieval Japan of a short-lived genre of painting referred to as sankei mandara (pilgrimage mandalas). The paintings are large-scale topographical depictions of sacred sites and served as promotional material for temples and shrines in need of financial support to encourage pilgrimage, offering travelers worldly and spiritual benefits while inspiring them to donate liberally. Itinerant monks and nuns used the mandara in recitation performances (etoki) to lead audiences on virtual pilgrimages, decoding the pictorial clues and touting the benefits of the site shown. Addressing themselves to the newly risen commoner class following the collapse of the aristocratic order, sankei mandara depict commoners in the role of patron and pilgrim, the first instance of them being portrayed this way, alongside warriors and aristocrats as they make their way to the sites, enjoying the local delights, and worship on the sacred grounds. Together with the novel subject material, a new artistic language was created—schematic, colorful and bold. We begin by locating sankei mandara’s artistic roots and influences and then proceed to investigate the individual mandara devoted to three sacred sites: Mt. Fuji, Kiyomizudera and Ise Shrine (a sacred mountain, temple and shrine, respectively). For each of the sites, we read the histories (political, religious, economic, social) and diaries (of pilgrims, monks and warlords), noting upheavals, power dynamics, and institutional relationships, and how these circumstances and relationships changed over the course of the 16th and early 17th centuries. We then apply this textual history to a formal analysis of each of the mandara devoted to the site, studying how the history of the site and the layout of the shrines and temples and the route to them are expressed in the pictorial language of the mandara, and we try to imagine how these paintings were employed and enlivened in etoki performances. Furthermore, by closely studying similarities and differences in choice and emphasis we show that the mandara, above their call for pilgrimage and donations, also encode the historical conditions at the time they were painted, capturing for example the tensions between religious groups and classes or the changing fortunes of a particular institution over time. This investigation thus aims to show how reading the artistic language of sankei mandara enlarges our understanding of a particular moment in Japan’s social and religious history, making these images valuable primary sources that enhance and supplement research in a wide range of fields.