Before Western contact, Maui had three major population centres: the southeast coast around Hana, the Wailuku area and the district of Lele (present-day Lahaina). In the 14th century, Pi'ilani, the chief of the Hana district, conquered the entire island and went on to accomplish some impressive engineering feats. He built Maui's largest temple, Pi'ilanihale Heiau, which still stands today, and an extensive islandwide road system.

The last of Maui's ruling chiefs was the powerful Kahekili. During the 1780s, he brought Oahu and Molokai under Maui's rule. In 1790, while Kahekili was in Oahu, Kamehameha the Great launched a bold naval attack on Maui and defeated Maui's warriors in a fierce battle at Iao Valley. He was forced to withdraw eventually, but the battles continued over the years. When Kahekili died in 1794, his kingdom was divided. In 1795, Kamehameha invaded once again and this time brought the whole island under his rule. He established Lahaina as his home in 1800, and it remained Hawaii's capital until 1845.

Whalers and missionaries arrived in Lahaina in the early 1820s, but they were soon at odds with one another. Shortly after arriving in 1823, William Richards, Lahaina's first Protestant missionary, converted Maui's governor, Hoapili, to Christianity. Under Richards' influence, Hoapili passed laws prohibiting drunkenness and debauchery. The whalers looked forward to indulging in grog and women after spending months at sea, and didn't take kindly to the missionaries' puritanical influence.

In 1826, when English captain William Buckle reached port, he was outraged to discover Lahaina had a new 'missionary taboo' against womanising. Buckle's crew came to shore seeking revenge against Richards, but a group of Hawaiian Christians came to Richards' aid and chased the whalers back to their boat. In 1827, Governor Hoapili arrested the captain of the John Palmer for allowing women to board his ship, and the crew retaliated with a round of cannonballs shot at Richards' house. The captain was released, but the laws - and tensions - remained.

After Governor Hoapili's death, laws against liquor and prostitution were less strictly enforced, and whalers again flocked to Lahaina. By the mid-19th century, two-thirds of the whalers entering Hawaii landed in Lahaina, which replaced Honolulu as the new favourite harbour. The whaling industry began to fizzle out by the 1860s, as the depletion of the last Arctic hunting grounds and the emergence of the petroleum industry spelled the end of an era. After the whalers left, Lahaina became all but a ghost town.

As whaling was declining, however, sugar was on the rise. In 1870, Samuel Alexander and Henry Baldwin, sons of prominent missionaries, began growing sugarcane on small plots in Haiku; the next year, they added hundreds of acres of the crop. It was the beginning of Hawaii's biggest sugar company. In 1876, the Alexander & Baldwin company began construction of the Hamakua Ditch, which carried water from the mountainous interior to the Haiku plantation. This system transformed Wailuku's dry central plains into green sugar land.

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