Asceticism had deep roots in ancient society, both in the various religious traditions of the Eastern Mediterranean and in the Greek philosophical tradition. However, the emergence of monasticism constitutes a strikingly rapid and radical change of social, political and religious culture. This chapter discusses asceticism and monasticism in the East during the fourth and fifth centuries. It presents a discussion of some general characteristic features that precedes a typological description of the main varieties and a sketch of the tradition's emergence in the five major areas: Egypt, Palestine, Syria, Asia Minor and Constantinople. In various ways the ascetic groups in the cities, as well as the ascetic households, were transformed into monasteries. In monastic communities, the spiritual direction of the disciple by his master or the answers of the solitary monks to those seeking advice were gathered and transmitted in growing collections of spiritual wisdom.