The history of Iwo, like many other ancient Yoruba settlements, is rooted in the distant past. It is closely intertwined with the history of the city-state of Ile-Ife, which is considered the cradle of Yoruba civilization. According to legend, the founder of the ruling dynasty of Iwo was Prince Adekola Telu, the son of Queen Luwoo Gbagida, the sixteenth ruler (Ooni) of Ife. Historians suggest that the migration from Ile-Ife occurred, by various estimates, between the 11th and 17th centuries.
The journey of the settlers led by Prince Telu was long and difficult. They stopped in several places but were forced to move on due to river flooding and attacks by wild animals. After the death of Adekola Telu, his followers, following the prediction of an oracle, continued their journey in search of a land where many parrots (Odidere) lived—a symbol of the promised land. The final settlement, which became the modern city of Iwo, was founded in the 17th century by a man named Olumade Parin, who became the first ruler with the title of "Oluwo."
Several key factors contributed to the development and prosperity of Iwo. The city's geographical position at the intersection of important trade routes connecting it with centers such as Ibadan, Oyo, and Ogbomoso was extremely advantageous. Its location on the border of the savanna and the forest zone created favorable conditions for agriculture. Trade and crafts also played a vital role: the economy was based on the cultivation of yams, maize, cocoa, and oil palm, and the city itself was known as a center for weaving and fabric dyeing using local indigo. Furthermore, Iwo's political role as the capital of the Yoruba kingdom of the same name provided its ruler, the Oluwo, with significant traditional authority.
From early on, Iwo was an important center of Islamic culture. It is believed that the first mosque in Yoruba lands was built here as early as 1655, making the city a hub for Islamic education. Alongside traditional beliefs, Islam became the dominant religion. The city's economy was significantly strengthened with the construction of the railway in 1906, which facilitated trade growth. Traditional crafts, such as weaving and wood carving, also played an important role in the city's life.