Nowhere in the Hawaiian Islands is there a more charming town than Wailuku, where the fascinating tale of its historic and cultural legacy is embodied in its building, streetscapes and vistas.

Home to Maui’s most famous Hawaiian rulers, site of Kamehameha’s decisive 1790 victory at 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.

The area was a center of power and population in pre-historic Hawaii. 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 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.

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.

Many homes and buildings in Wailuku town date from that earlier heyday. They offer a window into the past, providing a glimpse of plantation times, with its simple pleasures and enduring values. Along High Street, century-old Monkeypod trees and handsome residences reflect the town’s prosperity in the 1920s. Many private and public buildings have architectural and historical significance. Beyond this stylish neighborhood are the narrow lanes where modest bungalow, amidst colorful gardens, preserve the flavor of old Wailuku.

On upper Main Street (the road to Iao Valley), are remnants of the missionary era. A tiny graveyard contains tombstones of Hawaiian Ali’i (royalty) and missionary families. Further uphill are the Alexander House and Bailey House, now an excellent museum displaying ancient Hawaiian artifacts and missionary period rooms, and office of the Maui Historical society. A turn on Ilima Street to the top of Vineyard Street brings you to an interesting cemetery with lovely views of the Iao Valley and West Maui Mountains.

Follow Vineyard downhill through a charming neighborhood clustered around the Iao Congregational Church. The mature trees, varied architecture and serene vistas recreate the atmosphere of bygone days. As you approach the center of town, new buildings mingle with old, and former residences or commercial buildings have been rehabilitated for modern uses, keeping the colorful appearance of the past. In the business district, where false fronts and art deco facades stand shoulder to shoulder, sidewalks are shaded by canopies, inviting you to stroll and explore the charms of Old Wailuku Town.

Here the history and rich variety of Maui combine…here the past is always present…here you will understand that Wailuku is truly the heart of Maui!

Visit the Maui Historical Society website.

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Wailuku Maui