From Prehistoric times caves have been found in the township of Gaucin. A major complex of caves and paintings is near Benaojan, another village in the Ronda mountains.

The Iberians lived in Gaucín when the Phoenicians invaded. Ancient Iberian ceramics have been found in the castle's water deposit. The Phoenicians established gold mines on the nearby Sierra Bermeja and probably controlled Gaucín during their hegemony in the region.

The Romans found Gaucín the easiest place to access the Ronda mountain range from the sea to penetrate the interior, and they built roads to accommodate the traffic and the first castle.

The Visigoths invaded Gaucín in the fifth century. They named the town Belda and left a necropolis. In 1309 the Visigoth Guzman el Bueno, died fighting the Moors in front of the castle.

The Moors invaded in 714 by Gibraltar, using the Roman roads for their conquest. The village was re-named Gauzan (meaning rich village or hard rock) and as the western outpost of the Kingdom of Granada it was the site of many battles.

The Catholic King Henry IV finally conquered Gaucín in 1457. During the 16th Century the Moorish population (mudéjars) rebelled against the Catholic kings several times, killing soldiers and priests and causing mayhem.

The crown waged continual war against the malefactors. Many mudéjares crossed back over the Straits, but some became vagrants, and the town became depopulated and impoverished. Ruined farmers or decommissioned soldiers turned to banditry (bandolerismo,) hunting mudéjar vagrants to sell them into slavery, and preying on the local population. The British took Gibraltar in 1704.

By the end of the century many British Gibraltarians were coming to Gaucín in order to spend the summers in the cool mountains as they do again now. The French invaded Gaucín in 1808 during the Napoleonic Wars. Experienced mountain guerrillas, 700 strong, tried unsuccessfully to defend the castle, but the French won, razed 135 private houses, killed citizens and burned the municipal archives.

The French adventure impoverished Gaucín again and bandolerismo became a career. Bandoleros lived in caves and preyed on travellers and townsfolk, killing and robbing with impunity. Bandoleros are to be distinguished from the contrabandistas, smugglers who illegally imported English goods from Gibraltar.

During the Carlist wars in the 1830s the castle was repaired, fortified and provisioned by the Crown. However, the enemy captured it. At this time English settlers in Gibraltar started coming in greater numbers to Gaucín for its cool summer air.

During the Spanish Civil War more than 50 people were shot before the nationalists captured Gaucín in September 1936. Impoverished by war, many citizens turned again to contrabandismo and bandolerismo. Some became rich; the Guardia Civil shot others. Memories of this epoch are still vivid among the elderly of the village.

It's only the last 20 years, after Franco died and Spain entered the European Communion the economy is booming and the population now stabilizes thanks to tourism and building activities for mainly the British.