There is no specific historical record when Kalkan was founded, but one of the legends most widely accepted is that a woman from the Island of Meis came with a boatload of goods which she tried to sell to the villagers around the Kalkan area. Her venture proved so successful that other tradesmen from Meis followed her example and actually moved to Kalkan about 150 to 200 years ago, thus making Kalkan a small trading coastal post.
The original settlers were of both Greek and Turkish origin and were subjects of the Ottoman Empire . Still today the architectural style of the Kalkan resembles that of the houses in Meis (Castellorizo). Because of the mixed population, people started to call the village "Kalamaki" and it is thought that this name was derived from the Greek word "kalamari (squid)" which were plentiful in the surrounding sea. The building that many consider to be the symbol of Kalkan, the Mosque standing above the harbour was formerly a Greek Orthodox Church. This lovely building was built in the later part of the nineteenth century and the ornamented church bell, dated 1897, is now located in the Town Hall.
Within a period of 25 years, Kalkan rapidly grew to its present size and became a successful community. The growth of Kalkan can in all likelihood be attributed to the fact that Kalkan was the only easily accessible harbour between Kaş and Fethiye.
At the beginning of the 20th century, Kalkan had its own custom's house and in 1928, the first local elections were held. In 1937, the present elementary school was opened and it was one of the few elementary boarding schools in existence in Turkey at the time. There were also many restaurants and businesses established at this time
One of the major factors contributing to the decline of Kalkan's harbour trade was the vast improvement of the Turkish road system and in particular, the completion of the coastal road in 1960, which meant that goods could be moved from place to place overland.