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.
Kyparissia ilijengwa kwa njia ya maonyesho kwenye mteremko wa kilima, na iliitwa Arkadia katika Enzi za Kati. Asili ya Kyparissia imepotea katika enzi za kale. Kulingana na ripoti fulani, mji wa Kyparissia ulianzishwa kabla ya mwaka 1500 K.K. Eneo la kiakiolojia la Peristeria, karibu na mji huo, linaonyesha kwamba kulikuwa na makazi yenye ufanisi ya Wamikene katika eneo hilo. Jina la Kyparissia linatokana na miti mingi ya mti wa cypress (Kyparissia katika Kigiriki) ambayo ilikua huko au kwa jina la Mfalme Kyparissos. Homer, katika kitabu chake kikubwa cha Iliad, anataja Kyparissia kuwa mojawapo ya majiji makubwa zaidi ya Ufalme wa Nestor, mfalme wa Pylos. Karne kadhaa baadaye, Kyparissia ilipungua wakati wa Vita vya Peloponnesian, wakati Wamessenia waliposhindwa kabisa na Sparta. Hata hivyo, watu wa Kiparisia walipata kisasi chao wakati Thebans, wakiongozwa na Epaminondas, walivamia Peloponnesus mnamo 371 KK na kuikomboa Kiparisia, baada ya kuwashinda Waspartani. Chini ya utawala wenye fadhili wa Epameinondas, Kyparissa ilifanikiwa na ikawa bandari yenye ufanisi. Wakati wa utawala wa Mfalme Filipo wa Makedonia, ambaye aliwachukua nafasi ya Thebans, na wakati na baada ya uvamizi wa Waroma (165 KK), tunajua kidogo juu ya historia ya Kipaurisia. Yaonekana, Kyparissia ilipungua tena chini ya utawala wa Kiroma wenye upole. "Pausanias, mwanahistoria wa Roma, aliandika hivi: ""Kuna hekalu la Dafnio, hekalu la Apolo, na hekalu la Athena." Katika enzi za kati, Kyparissia ilikuwa mji mkuu wa barony ilianzishwa na Franks hadi 1430 wakati Thomas Paleologos kufukuzwa Franks kutoka Peloponnese. Hata hivyo, ukombozi wa mji huo haukudumu kwa muda mrefu, kwani Waturuki waliwashinda wakazi waliokuwa wakijificha ndani ya ngome na kuishinda mji huo mnamo 1460. Kati ya mwishoni mwa karne ya 17 na mwanzo wa karne ya 18, Kyparissia ilikosa nguvu chini ya utawala wa ukandamizaji wa Waveneti ambao walikuwa wamewatawala kwa muda mfupi. Utamaduni wa Waveneti ulianza kuenea sana wakati wa vita vya kwanza vya Uturuki mwaka 1715. Wagiriki walianza mapinduzi yao dhidi ya Uturuki na hatimaye walipata uhuru wao mwaka wa 1821.