Church, castle, and city are the central locations in the development of literature in Latin and the vernacular in the thousand years we call the Middle Ages. It was a time of great changes. Around 500, literature as we know it was virtually non-existent (stories were transmitted as remembered and retold words; only Latin texts were committed to parchment), whereas around 1500 printed books were in circulation, and the common people as well as clergy and nobility, could read. In the form of medieval romance, the modern novel is born; worldly love becomes the foremost theme for songs, narratives, and plays. In this chapter, the history of medieval Europe is used to contextualize what happens in culture and literature. The building of castles and courts led to courtliness, courtly love and the love songs of the troubadours; the growth of cities provided a new audience for playwrights, but also for religious masterpieces like Dante’s Divine Comedy. The socially varied population of the city is reflected in the cast of Chaucer’s Canterbury Tales. The courtly culture of France takes a central role in this chapter, because its literature radiated out to all parts of Europe during the High Middle Ages.