Mykalessos suffered along with the rest of Boeotia during the Greco-Persian Wars, especially during the Battle of Plataia. Furthermore, around the time of the Peloponnesian War, the local militia burned the village down.
After the fire died down, the northern part of the village was claimed by bandits, and it became their base. West of the village were the beginnings of the bridge to Euboea, crossing the Euripos Strait. Southeast of the village was located the Snake Head Rock, which offered a good view of the burnt polis.