Shortly after the Protestant Missionaries arrived in 1820, they built the first schoolhouse in Honolulu. They learned Hawaiian as rapidly as they could and started the process of creating a written Hawaiian language, as before it had been only oral. The Hawaiians responded well to the offers of schooling. At first, the missionaries taught only those of chiefly class, then as many other adults as they could. The adults with newly-acquired literacy then taught more adults and children.
Protestant missionaries brought Western-style education to Olowalu probably in 1826, when students attended school either in the open air or in a thatched hut. The first school for commoners in the Kingdom of Hawai`i had opened in Lahaina just two years before. The school at Olowalu also served and was termed a "common school" or "native school.. In 1835 when the Olowalu Church was built, classes were held there. Initially the Lahaina Protestant mission station both funded and supervised the school. However, by 1840, the Kingdom of Hawai`i took over financial support of all common schools leaving supervision to the mission, which continued to incorporate religious lessons until the 1850s or 1860s.
It is likely that the Catholic mission established a one-room school at Olowalu during the 1840s, conducted by a native Hawaiian and supervised by a priest. If so, it lasted only a short time.
At Olowalu School Hawaiian continued as the language of instruction until 1890. Reverend S. K. Kamakahi, who doubled as both the minister at the Olowalu Church and the school's only teacher, taught from 16 to 24 students from at least the early 1880s until the changeover to English language instruction in 1890. Instruction was provided only for the young, usually up to the fourth grade.
When the school converted to English language instruction, officials enlarged the building and enrollment jumped to 35. The yearly budget for Olowalu School for the period 1890-1892 was set at $416, in addition to a yearly salary for the British-born teacher of $500. The Department of Public Instruction supplied a cottage as housing for the teacher at the beginning of the century and built a new school building on a new site in 1908. A burgeoning school population of 62 children in 1911 necessitated the expansion of Olowalu School from one room and one teacher to two rooms and two teachers. It may have been in this year of expansion that instruction was expanded to the fifth and sixth grades. Enrollment hit a high of 91 in 1912.
Over time enrollment declined and the school reverted to using one teacher. In 1931 only 37 students attended Olowalu School. On January 4, 1932, Olowalu School closed. Students from Olowalu traveled to Kamehameha III School in Lahaina for their education, using transportation provided by the County of Maui.