During the second half of the 14th century the arts and crafts received a significant impetus as well as the art of decorating church books with exquisite miniatures. Time has spared for us two books which were decorated on the order of Tsar Ivan Alexander — a Bulgarian translation of the Chronicle of Manasses, a Byzantine chronicler, and a Tetraevangelicum. These masterpieces not only of the Bulgarian, but also of the European Middle Ages, which are an irreplaceable source of Bulgarian history, are kept among the most valuable manuscripts in the Vatican Library in Rome, and in the British Museum in London.

It is difficult for secular literature to flourish in a doomed and declining country, and that is why Bulgarian literature of the 14th century does not have its Dante and Petrarca. Instead of this, however, Bulgarian literature gave to the Eastern Orthodox world religious writers of exceptional stature. During Ivan Alexander's reign the Kilifarevo Monastery near Turnovo became a centre of very lively literary and cultural activities. It was here that Theodosius of Turnovo worked, an eminent theoretician of Hesychasm, – a religious teaching preaching extreme mysticism and asceticism, which was also called 'miLitant Orthodox Christianity'.

The Kilifarevo School turned out a number of prominent theologians and religious writers, disciples of Theodosius of Turnovo. The most famous among them was Patriarch Evtimi – the last Bulgarian patriarch before Bulgaria was conquered by the Turks. In the course of five years he managed to set up a whole university in the small monasteries near Turnovo; there, besides Bulgarians, foreigners also studied, mainly Russians, Serbs and Romanians. Patriarch Evtimi is the author of scores of works, whose religious content does not hide his original literary style, rich in artistic comparisons, vivid natural pictures and militant patriotism. Of particular importance was the spelling reform introduced by Patriarch Evtimi, whose aim was to create a unified literary language. The literary style of the entire Turnovo School was characterized by an elevated lofty tone aimed at causing a patriotic upsurge among the Bulgarian people, to prepare them for the forthcoming bloody battles with the Ottoman invaders.

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