The discovery and colonization of the island is shrouded in mystery. The first reference to São Jorge dates from 1439 and it is known that, around 1470, when there were small groups of settlers in the west and south coasts and the town of Velas was founded, the Flemish nobleman Wilhelm Van der Haegen, famous for his virtues, came to the island and settled in Topo. Now his name has been translated as Guilherme da Silveira.
The settlement of the island with people from the north of the Portuguese mainland must have been fast, as well as its prosperity because its captaincy was given, in1483, to João Vaz Corte Real, Angra donee, in Terceira, and the city of Velas received its charter before the end of the 15th century. Topo was the Council in 1510 and Calheta in 1534, showing the vitality of an economy that, apart from the vine and wheat, had in the cultivation of Pastel and the harvest of wheat, exported to Flanders and other European countries, and used in dyeing, the main productions.
The dynastic crisis caused by the ascent to the throne of Portugal of the King Philip II of Spain had its repercussions in São Jorge, which, as well as Terceira, supported Dom António, Prior do Crato, also pretender to the throne and it was only capitulated to the Spaniards after the fall of Terceira in 1583. It is followed by a period of centuries in which the island remains quite isolated especially because of the precarious shelter offered by its ports to ships, to its limited economic importance. Even so the attacks by British and French privateers during the 16th and 17th centuries and the devastating raids by the Turkish and Algerian pirates keep happening. At the end of the 16th century a section of the squadron under the command of the Count of Essex landed in the cove of Calheta.
To fight back the inhabitants threw heavy stones - the only weapons they had – and a soldier named Simão Gato, faces an official of the enemy force, knocks him down and steals the flag from him. In the 18th century the French privateer Du-Gnay Trouin loots São Jorge, and in 1816, an Algerian corsair, who tried to seize a merchant vessel, was driven off by shots from the fortress of Calheta. Other calamities worried S. Jorge’s inhabitants. They are food shortage and hungry due to the poor harvest years, since the 16th century to the 19th century, earthquakes and the volcanic eruptions of 1580, 1757 and 1808.
The isolation of the past has been broken with the improvements made in the two main ports - Velas and Calheta - and the airport, opening new horizons to the prosperity and progress of Sao Jorge, making total use of its natural resources, expansion of livestock and dairy, fishery and canning industry.