The ancient Hawaiians of Olowalu lived in the largest and deepest valley in southwest Maui. The valley and its upland area comprised a land division called an ahupua`a, a pie-shaped area designed to provide the various resources a community required to thrive. Hawaiians supported themselves by growing kalo
(taro)in extensive lo`i
(irrigated terraces), and by cultivating `uala
(sweet potato), `ulu
(breadfruit) and niu
(coconut), made possible by water that flowed out of the West Maui Mountains through Olowalu Stream. Olowalu was particularly suited for growing `ulu
in the lower areas of the valley and `uala
on the kula
(open field) lands closer to shore. Both kalo
served as principle food sources along with fish caught along the coast.
Several archeological sites at Olowalu have been identified as having been used for religious purposes. Due to its size and location, the Kawaialoa (or Kawaloa) heiau was likely used for major religious ceremonies involving high chiefs. This suggests that Olowalu played a significant role in religious matters in the moku (district) of Lahaina. Hawaiians probably used another medium-sized heiau still remaining in Olowalu for local rituals. Smaller shrines still extant at Olowalu indicate use as fishing and agricultural shrines used by one or more families.
Though gone now, a fishpond did exist in pre-contact Olowalu. It was located in the low areas just behind the coastal dunes. These were swampy lands resulting from intermittent run-off and possibly springs. Hawaiians converted these swampy lands into a fishpond for the growing of fish for the high chiefs. Oral history indicates that this fishpond was named Kaloko o Kapa`iki and dates back at least into the 1700s.
Olowalu contains one of the largest collections of petroglyphs on the island of Maui with at least 72 petroglyphs. They are close to a natural rock overhang at the base of a cliff, which was probably used as a camping site or resting place, so it is probable that at least some of them were created by travelers using the `Iao-Olowalu Pass. Two panels of petroglyphs hold representations of many human forms, some in interaction and some holding objects such as spears and paddles. The petroglyphs also show dogs, horses, fish, outrigger canoes, early historic writing, circles and several indistinct forms.
Travelers to Olowalu could follow the Alaloa, the great highway that encircled Maui. Canoes and paddlers stationed at the mouth of Olowalu Stream allowed travelers from Lahaina to avoid crossing the stream in times of high water by transporting them via the ocean, sometimes as far as Ma`alaea. Chiefs of West Maui traveled the Alaloa, usually carried on maneles
(litters) by human bearers, to acquaint themselves with the people and to maintain their power. Tax collectors paid a yearly call during the makahiki
(harvest) season from October to January.
If speed was needed between East and West Maui, travelers utilized the `Iao-Olowalu Pass. The route, considered one of the most difficult and dangerous on Maui, proceeded five miles into Olowalu Valley and then climbed over into `Iao Valley. The importance of this trail is illustrated by its use in wartime; Kalanikapule, son of the great Maui chief Kahekili, used it to escape from Kamehameha after his defeat in the Battle of Kepaniwai.