This essay investigates the two most significant vitae dedicated to St Cuthbert, namely Bede’s Latin prose Vita S. Cuthberti and Ælfric’s Old English Life of St Cuthbert, and, through these two crucial texts of Anglo-Saxon hagiography, it discusses the Anglo-Saxon appropriation of the desert ideal as well as of the legacy of the Desert Fathers. By challenging the interpretative categorisations and dichotomies that have traditionally been applied to the history of the Anglo-Saxon monasticism and keeping to a close reading of primary sources instead, this study explores how the two major literary voices of Anglo-Saxon monasticism, Bede and Ælfric, read their Eastern antecedents in their representations of Cuthbert’s eremitic vocation. Beyond their – inevitable – differences, the comparative analysis of the Cuthbert hagiographies by Bede and Ælfric yields a fundamental continuity in the way of articulating the two crucial elements of the Christian paradigm of sanctity, the active and the contemplative, which is distinctively Gregorian. It is under the aegis of Gregory’s synthesis of contemplation and pastorate that Cuthbert’s multifaceted vocation unfolds as an exemplary prototype of the characteristically multifarious Anglo-Saxon monasticism.