Given its proximity to Terceira, it is believed that the Portuguese navigators discovered São Jorge Island along with the other islands that surround it. As the second island to be inhabited in the Central Group, it is believed that it started to be populated around 1460. A decade later, several settlements were already established on the western and southern coasts, including in Velas. The arrival of the Flemish noble Wilhelm Van der Haegen marks the foundation of the Topo community in the east end of the island.
In 1483, the captaincy of São Jorge Island, which was developing rapidly, was given to João Vaz Corte Real, who was at the time the captain of Angra do Heroísmo on Terceira Island. A town charter was awarded to Velas at the end of 15th century, a status that was also extended to Topo in 1510 and to Calheta in 1534. The prosperity of the island came from wheat, but from early on the island also stood out for the quality of its pastures.
Left to a certain isolation due to the lack of safe ports, São Jorge Island progressively lost its economic influence. In the 16th and 17th centuries, the island was visited by the unwelcome English and French privateers, as well as by the ruthless Turkish and Algerian pirates. The Du-Gray-Trouin incursion in Velas in 1708 became famous. Defeated by the people’s heroic resistance, the French corsair left São Jorge Island with many casualties in his crew.
From the 16th to the 19th centuries, the inhabitants’ lives were hit by agricultural crisis, which caused food scarcity, and by earthquakes and volcanic eruptions, which caused great destruction. Similarly to other islands, the economy was based on agriculture and cattle breeding, namely on wheat and vineyards, on the extraction of orchil, and on livestock that from early on generated important secondary sectors linked to cheese and wool. The fishing industry became important between the end of the 19th and the 20th century, first through whaling, and since the 1960s, through the fishing of tuna. Currently, the excellent quality of the pastures of São Jorge has become evident in the production of the island’s typical cheese made from raw cow’s milk. São Jorge Cheese is a protected designation of origin, and the island is a demarcated region for its production. The island’s airport and the modern ports of Velas and Calheta have contributed to the full integration of São Jorge Island into the Azores Archipelago and into the world.