The first reference to Sigri is made by the historian and geographer Strabo (65 BC–23 AD), who, referring to the dimensions and boundaries of the Hellespont, writes ‘Now as one sails from Lectum to Assus, the Lesbian country begins at Sigrium, its promontory on the north.’ :
In the 2nd century AD, Arrian in his Anabasis of Alexander, referring to the Siege of Mytilene, wrote: ‘A part of his fleet guarded their harbour, and, intercepting the ships passing by, he kept the rest of his fleet as a guard off Sigrium, the headland of Lesbos, where is the best landing-place for trading vessels from Chios, Geraistos, and Malea. By this means he deprived the Mitylenaeans of all hope of succour by sea.‘
Until the Renaissance, there is no mention of Sigri from other historians. However, it appears on maps by early European cartographers under various names Porto Sigri, or Castelo Seguro, or Sigrium amongst others.
Systematic archeological excavations have not been carried out in Sigri and therefore information about the settlement of the area is limited. However, scattered ruins in the wider area of Sigri show that it has been inhabited since ancient times. In Paliokastro, Ag Giorgos, Oikia, and elsewhere, the ruins of past lives invite us to explore. The main occupation would have been farming, and at Adamania the ruins of an old olive press have been found.
With the subjugation of Lesvos to the Venetian nobles Gatelouzos (1355–1462), the main settlement of the area was Agia Theodori, north of today’s Sigri.
In 1331, besides the Monastery of Ypsilou, other documented monasteries were: Agia Theofanous (in Agia, north of Antissa), Klimation (at the intersection of Sigri–Antissa–Eresos), Keramonos (in today’s Keramos), and Kreokopou.
Another church that was used until a few years ago is Panagia Vascana (in Metochi).