In the twelfth and thirteenth centuries, Kirkwall was a major cultural, political and religious centre in the Norse world, with links east, south, west and north. It was a locus for poetic innovation, developments in prose narrative forms, cutting-edge architecture, religious and secular music and much else. However, there is little evidence for literary activity in the Northern Isles after the mid-thirteenth century. Two hundred years later, the Orkney earldom had been transferred from Scandinavian to Scottish overlordship, with the Black Death of 1348 an important turning-point in this process. This represented not only a political, but a major social, cultural and linguistic shift for Orkney and its northern neighbour Shetland. The paper will start by charting the complex linguistic situation of this transitional period, involving Norn, Norwegian, Danish, Latin and Scots, and attempt to identify the effects of this complexity in the surviving record. It will then go on to tease out evidence for the fate of literary activity in the fourteenth and fifteenth centuries, using (of necessity) a broad definition of literature which includes poetry, chronicles, hagiography, myth, folklore and even the law. The regeneration of Orcadian culture was a complex process that in many ways still reached back to its Norse origins while accommodating new political and linguistic realities.