The paper presents the current work on the digital edition of the church chronicles of the Orthodox Metropolitan See of Philippopolis, or Plovdiv, in today's Bulgaria. This peculiar set of volumes, known as kondika in Bulgarian or codix/codicas in Greek, is written in Greek and contains the annals of the region of Upper Thrace from the end of the 18th century until the late 1800s. This is a historical period of great turmoil, several wars and revolutions, the crisis of the Ottoman Empire and the creation of the modern nation-states on the Balkans. During the decades encompassed in the 4 volumes of these codices, the Episcopate of Philippopolis/Plovdiv passed from the Ecumenical Patriarchate in Constantinople to the newly-created Bulgarian Exarchate and fell within the boundaries of three successive states: the Ottoman Empire, the protectorate of Eastern Rumelia, and the Bulgarian Principality. In the chronicles of the See, we encounter information about taxes and donations, properties and changes thereof, marriages and deaths, the sustenance of monasteries, schools and hospitals in the region and their costs, local political, cultural and religious life and its protagonists. The digital edition of these annals, a contribution to DARIAH-EU on the part of the national Bulgarian consortium CLaDA-BG, suggests diverse activities from the editing of the original handwritten Greek text and its translation to the annotation of personal and place names, institutions and organizations, events and other entities as well as the creation of indices, vocabularies, notes and commentaries targeted at the scholarly community and the general public. The workflow is divided into several stages and includes researchers and assistants at various levels of their career. The present paper focuses on methodological challenges such as the recognition and annotation of different named entities in the text, the creation of indices that could serve as digital multilingual prosopographies and gazetteers of the historical period, and also the online publication of the annotated texts, original and translational, as a parallel aligned edition. The potential for further development of the digital edition in the context of the national consortium is also explained. Institutions such as the Ivan Vazov National Library of Plovdiv and the Ethnographical Museum to the Bulgarian Academy of Sciences are also content providers to CLaDA-BG. The former is currently conducting large-scale activities on the digitization of historical newspapers from the region of Plovdiv from the 1800s largely containing references to the same people, places and events that could be encompassed in a big searchable meta-collection together with the church annals. The latter is bound to provide materials to be included in CLaDA-BG's digital collection of historical artefacts from everyday life and popular culture which can also serve as illustrations to the notes in our digital edition about objects characteristic for 19-c. Thrace but virtually unknown to today's average user. Last but not least, the dataset extracted from our digital corpus will be integrated into a detailed knowledge graph of our country and region from different periods derived from different sources.