In the early 20th century Wailuku was the main tourist destination on Maui, though it has since been eclipsed with the rise of the resort towns such as Kaanapali.

[citation needed] Home to Maui's most famous Hawaiian rulers, site of Kamehameha's decisive 1790 victory at the Battle of Kepaniwai in the Iao Valley, location of the 19th century Mission Station and birthplace of the mighty sugar industry, Wailuku illustrates the powerful influences which shaped the town, the island and the state.

In the mid-1800s it was irrevocably changed when New England missionaries brought their religious beliefs, western skills and implements and new agricultural methods.

By the 1860s the Wailuku Sugar Company (owned by C. Brewer & Co.) and other plantations were busy growing and milling sugarcane.

Miles of ditches were dug, bringing irrigation water from deep in the mountains to the vast fields of central Maui, and the sugar industry flourished, to the detriment of the native people.

Thousands of skilled and unskilled workers immigrated to Maui from all parts of the world to toil in the fields and factories.

They came from China, Japan, Okinawa, Korea, the Philippines, Europe, America – bringing ethnic, cultural and religious diversity to their new home.

Many settled in Wailuku, where houses, schools, churches, temples, shops, banks and community buildings were built to meet the needs of the thriving company town.

In 1905, Wailuku was designated Maui's County Seat, and it soon became a hub of government, business and entertainment, boasting vaudeville and movie theatres, bowling alley, hotels, poi factory, ice and soda works, and many markets and offices.

Thus began the era of growth which continued until the late 1960s when the sugar industry, losing its economic prosperity, reduced operations and the development of alternative commercial centers drew business away from Wailuku's downtown streets.

Beyond this stylish neighborhood are the narrow lanes where modest bungalow, amidst colorful gardens, preserve the flavor of old Wailuku.

Maui's ruler Kakaʻe, in the late 15th century, designated ʻĪao Valley as an aliʻi burial ground.

In 1790, the Battle of Kepaniwai took place there, in which Kamehameha the Great defeated Kalanikūpule and the Maui army during his campaign to unify the islands.