During his reign (ca. 1450), Aliʻi nui (ruling Chief) Pi’ilani, the 15th King of Maui gained political prominence for Maui by unifying the East and West of the island, bringing rise to the political status of Maui. Local history reveals that Pi’ilani organized great public works projects, which are still evident today such as the King’s Road in West Maui (Hono-a-Pi`ilani Trail), fishponds, irrigation, and religious architecture including the largest Heiau in Hawai’i (sacred Hawaiian temple), Hale O Pi’ilani, which still stands today along the Road to Hāna.
In the early 1500s, King Pi’ilani’s son, Aliʻi nui (Ruling Chief) Kiha-a-pi’ilani extended his father’s footpath (King’s Road) into the Hana District not only along the coast, but also up the Kaupo Gap and through the summit area and crater of Haleakalā. Portions of the Road to Hāna are a remnant of this 16th century coastal footpath or alaloa (long road), and also known as the King’s Highway, King Kiha-a-pi‘ilani Trail or even Kipapa o Kiha-a-pi’ilani (the pavement of Kiha-a-pi’ilani).
After completion of the footpath by Kiha-a-pi‘ilani, the King’s Road was the only alaloa to completely circumnavigate an entire Hawaiian island. It was paved with hand-fitted basalt (lava) rocks, and was 138 miles (222km) long and 4 to 6 ft. (1.2m to 1.8m) wide. The road was used for the 4-month annual harvest festival of Makahiki and to collect taxes, promote industry, enforce order and move armies. This footpath to Hāna was well maintained for the next 250 years.
Since there were no bridges, some beaches on the east side of the alaloa along Route 360 were often used to cross gulches. It has also been reported that travellers resorted to swinging on homemade ropes made of vines to cross the abundant east Maui streams and used treacherous staircases carved into the cliffs to cross the deep gulches.
Around 1759, the King of the Big Island, Kalaniʻōpuʻu, captured Hāna and held it for more than twenty years. The footpath soon fell into disrepair and in 1780, Kahekili, the King of North Maui, retook Hāna, repaired and reopened the road and made improvements by building wooden bridges. The road could only support foot traffic until around 1900, by which time Hāna had become a thriving sugar plantation community, relying on foot and horse paths along the irrigation ditches, travel by canoe or weekly steamship service for travel to central Maui.
Fading into history, most of King Kiha-a-pi’ilani’s East Maui Trail of the alaloa has been paved over by modern roadways, including the Road to Hāna or destroyed by agriculture. A section of Kiha-a-pi’ilani’s alaloa can still be walked along the Road to Hāna today at Wai’anapanapa Beach Park.