Kosmas' Chronicle – in the so-called Chapter Manuscript from the 14th century – reporting the death of Prince Slavník in 981, with a mention of Litomyšl. It was originally a protective fortified settlement of the Slavník principality on a significant trade route, defending a forested border area against Moravia.

which he gave Litomyšl municipal rights. In the first privilege, he confirmed all the previous privileges of the monastery so far, with a brief remark that he gives the same rights and freedoms to Litomyšl that royal towns enjoy. The town elected its mayor and 12 councillors. In the second document the king defines its privilege in more detail, Litomyšl is named as the property of the Monastery of Our Lady, and it is given judicial, municipal and market rights to the same extent as other royal towns.

The extensive conversion was designed by Giovanni Battista Aostalli (1510–1575). Older buildings belonging previously to Kostkas of Postupice were adapted for the east wing, the north corridor and the connecting wing. The west wing is a new Renaissance building with a partial use of older cellars. The rich sgraffito decoration, consisting of stylised 'envelopes' (about 8000 different envelopes on the facade of the castle) and figural (themes from the Old Testament, from ancient times, battle scenes on the north wall of the 2nd courtyard) was created by a group of Italian builders and stonemasons. The Pernštejns also built a chapel dedicated to St. Monica inside the castle. After the Pernštejns, the Trauttmansdorfs got possession of the castle, after which the Wallenstein-Wartenberg family settled there and had the interiors modified in the Classicist style. The castle was put up for auction in 1855, in which it was bought by the Thurn-Taxis, who however did not live in the castle. Nevertheless, the castle remained in their possession until the end of World War II, when it was confiscated on the basis of presidential decrees. The compound is a rare example of the conversion of an Italian Renaissance palace; on the ground floor of the aristocratic residence a unique Baroque theatre with functional machinery and a set of backdrops has been preserved.

World Heritage Committee decided to inscribe the castle grounds on the UNESCO World Heritage List.