Built amphitheatrically on the slopes of a hill, Kyparissia was called Arkadia in the Medieval Times. The origins of Kyparissia are lost in antiquity. Some accounts place the founding of Kyparissia somewhere before 1,500 B.C. The archaeological site of Peristeria, close to the town, shows a prosperous Mycenaen settlement in the area. Kyparissia got its name either from the abundant cypress trees (Kyparissia in Greek) that would grow there or from the name of King Kyparissos. Homer, in his great epic Iliad, mentions Kyparissia as one of the largest cities of the Kingdom of Nestor, king of Pylos.

Several centuries later, Kyparissia declined during the Peloponnesian War, when the Messenians were decisively defeated by Sparta. However, the people of Kyparissia got their revenge when the Thebans, led by Epaminondas, invaded Peloponnese in 371 BC and liberated Kyparissia, after defeating the Spartans. Under the benevolent rule of Epameinondas, Kyparissa flourished and it became a prosperous seaport.

During the Macedonian rule of King Philip, who supplanted the Thebans, as well as during and after the Roman invasion (165 A.D), we know little about the history of Kyparissia. Apparently, Kyparissia declined once again under the mild rule of the Romans. The historian Pausanias provides information about the temples that existed in the area, including the Temple of Dafnios Apollo and the Temple of Athena Kyparissia. In the Medieval Age, Kyparissia became the capital of the barony founded by the Franks till 1430 when Thomas Paleologos expelled the Franks from the Peloponnese.

However, the liberation of the town was short-lived, as the Turks won the inhabitants that were hiding inside the Castle and conquered the town in 1460. Between the late 17th century and the beginning of the 18th, Kyparissia languished under the oppressive rule of the Venetians who had briefly supplanted the Turks. The tyranny of the Venetians soon came to an end with the return of the Turks in 1715. The Greeks launched their great revolt against the Ottomans and finally gained their independence in 1821.