Preaching in Thessaly
After leaving Mount Athos, Damian traveled through the regions of Greece preaching the word of God, calling Christians to repentance and to turn from injustice and evil deeds, and exhorting them to keep the commandments of God. Greek accounts trace his missionary path through the area of Mount Olympus and on to Larissa and Mount Kissavos (Ossa), and eventually into the Agrapha region of his birth.
Greek tradition further holds that he established and largely rebuilt monastic houses during this ministry, including a monastery on Mount Kissavos and the rebuilding of the Monastery of the Panagia Peleketes at Karytsa, and that part of his preaching urged Christians not to engage in commerce on Sundays — a message the Ottoman authorities are said to have regarded as a disturbance of the markets.