According to the majority of Canarian pre-historians the initial colonisation of La Gomera took place at around 500 BC. At the time of the 15th century Spanish conquest the island was divided into four districts or cantons, where the aboriginal population lived around the most important gorge on their territory.

Hipalán covered major parts of the present day boroughs of San Sebastián and Alajeró, Mulagua coincided with the boroughs of Hermigua and Agulo, Orone covered Valle Gran Rey and parts of Alajeró, and Agana coincided with the valley of Vallehermoso. The social and political control of each canton was assigned to a single leader or mencey, with the concession to exploit the apportioned territory from the coast up to the mountains and hillsides.

In the 15th century the conquest and subsequent colonisation of La Gomera by the Spanish established a lordship regime on the island in the person of Hernán Peraza the Elder, who was the first in a series of twelve lords to rule the insular territory. The despotic rule and enslavement policy of his successor Hernán Peraza el Mozo faced tenacious resistance by the natives, leading even to his death by the hands of an aboriginal warrior Hautacuperche in the year 1488.

Following this event there was ruthless repression carried out by the ruler of Gran Canaria, Pedro de Vera, who executed many Gomerans or sold them as slaves, introducing a proper feudal regime on La Gomera. This new regime brought about the change from collective to feudal ownership of the land, where the lords granted or leased plots of land to colonists, which in turn served to contain emigration and to guarantee labour. The feudal economic model was devoted in the north of La Gomera to farming export crops like sugar cane, whereas the south was cultivating cereals to supply the insular market.

The importance of La Gomera in navigation was based on its status as one of the main ports of call for Atlantic shipping, as was shown by Christopher Columbus himself in 1492 on his voyage to discover America. The port of call status augmented commercial activity which enabled the island to sustain relations with many European ports, with significant participation by Flemish and Genoese merchants. Unfortunately the commerce attracted pirates as well, who plundered the village of San Sebastián on several occasions during the 16th century.

The institutional setting of La Gomera changed at the beginning of the 19th century with the elimination of the feudal lordship, and the landowners sold their property to private citizens representing the agricultural middle class either from the island or overseas. All the same this process did not solve the penury of the Gomeran farmer, who continued to work as an underprivileged sharecropper for the landowners.

This condition led many of them to choose emigration as the only way out of the harshest way of life and working to which they were subjected. The scarce population left on the island continued farming traditional crops like potatoes, maize, vegetables, etc. for subsistence, along with some export crops such as wine, silk, cochineal, etc.

After the cochineal crisis towards the end of the 19th century, new irrigated crops for export were introduced: tomatoes and bananas were grown in the lower lying coastal areas and along valley floors, leading to the appearance of new settlements. Thus the beginning of the 20th century showed the greatest population growth in the island’s history, reaching almost 30.000 inhabitants, but soon after in the second half of the century the crisis of domestic agriculture resulted in a mass emigration to Venezuela and Tenerife, leaving La Gomera with only 15.000 inhabitants.

Since 1970s the unexpected boom of tourism and construction industry, aided by the creation of a regular ferry link between San Sebastián and Los Cristianos in 1974, has consolidated the growth of southern tourist resorts like Playa Santiago and Valle Gran Rey, leaving rest of La Gomera in a state of indeterminacy and agricultural decadence.