This thesis examines the destroyed thirteenth-century monastery of Lykousada, located at Loxada, in Thessaly and founded by the nun Hypomone. A surviving chrysobull issued by Andronikos II in 1289 mentions Hypomone exclusively in terms of her monastic foundation. An analysis of the lands belonging to the monastery place Lykousada within thirteenth- and fourteenth-century religious, cultural, and ethnic networks of the region. Lykousada presents the only example of a Byzantine monastery founded by a Vlach. By focusing on the architectural commissions and properties of this elite nun, my study investigates the material culture left by the transhumant group. I examine the repetition of thirteenth-century architectural models from Epiros to Thessaly to uncover features of Hypomone’s monastery. A study of Vlachs— encapsulated in the story of this elite nun—demonstrates their indispensable role in Thessaly. The medieval roads that connect Hypomone’s estates indicate the boundaries of her influence and power, and subsequently that of her Vlach ancestors.