In popular imagination, La Mancha is the vast, arid plain where Don Quijote tilted at windmills. As you travel through the region, you’ll first see modern wind farms, then—on the occasional hilltop—an array of old-fashioned windmills or the ruins of a medieval castle. Or both. On escarpments high above winding rivers, its cities are reminders of Spain’s turbulent past. Every culture from the Romans on made Toledo its citadel; siege was a way of life. Yet the dramatic settings have proved as important to art as to war. El Greco looked out from the walls of imperial Toledo and saw the earth far below and the heavens at eye level—a perspective repeated again and again in his paintings of the Ascension. The eastern city of Cuenca, perched above a deep river gorge, became a haven for abstract artists in the 20th century; its hanging houses (casas colgadas) cling to the rocks like a cubist fantasy.

The name Castilla-La Mancha is a modern administrative fusion of two age-old territories: The first part means land of castles, the second comes from the Arabic al-mansha, meaning parched wilderness. The monotonous tableland (meseta) supports wheat, olives, sunflowers, herds of sheep and endless, industrial vineyards. The region’s celebrated cooking reflects the landscape: roast game and stews, saffron and paprika, hard sheep’s cheese, and good red wine.