Although it appears to be the quintessential American small town, Wailuku is also firmly rooted in the mix that makes Hawai‘i unique: ancient Hawaiian legends, missionary influence and sugar plantation immigrants. The seat of government for Maui County, Wailuku is framed by the verdant, majestic peaks of Hale Mahina in the West Maui mountain range and the expansive, fertile basin that connects with Haleakala crater to form the island of Maui.

Historically, Wailuku is best known for the wars that the Hawaiians of old waged in its valleys and streams. The high chief of Maui, Kahekili, launched invasions of neighboring islands by canoe from here, and in 1790, his son Kalanikupule fought a legendary battle against the fierce Kamehameha for control of the island. The Maui forces were slaughtered by the warriors from Hawai‘i and their fallen bodies clogged the stream which flows out of ‘Iao Valley. From then on, the battle was known as kepaniwai (“damming of the waters”), and the area was called wailuku (“water of destruction”).

The area’s sacred place, ‘Iao Valley, is revered for its spiritual value and spectacular natural scenery. Over 100 years ago, visitors began flocking to the valley and its famous needle peak. The lookout toward the peak is 133 steps up, or about a 30-minute walk. Cross the scenic bridge over the stream, and walk down into the grove to check out the garden of native Hawaiian plants. Sounds of the rushing stream echo off the sheer mountain sides. This is a place for calm reflection as well as invigorating hikes.

Just down the road is Kepaniwai Park, or “Heritage Gardens.” It offers outstanding displays of the ethnic groups that make up Maui’s citizenry. Explore architectural examples and plant gardens of Hawai‘i, New England, Portugal, The Philippines, Japan, China and Korea, along with a monument to Puerto Rico. It’s an excellent picnic spot, too. Kepaniwai Park has free admission, ‘Iao Valley has a parking fee, and both are open from 7am to 7pm daily.

Leading out of the valley and approaching Wailuku Town on the right, stop and visit Bailey House Museum & Gift Shop. It’s open Monday-Saturday from 10 am to 4 pm, and features a collection of missionary-era memorabilia, paintings and koa furniture, as well as displaying Maui’s largest collection of pre-western contact Hawaiian artifacts. It is also home to the Maui Historical Society and its archives of historical photos, particularly from the plantation days.
Wailuku Town itself is worth exploring on foot - there’s a large public parking lot between Market and Church Streets which is centrally located. Recently experiencing a boom period of gentrification, the old buildings are being restored to their former glory and downtown is fast becoming home to many artist boutiques, clothiers, antique and collectible shops, and several restaurants. Main Street, Market and Vineyard Streets are filled this eclectic array of vendors. A notable landmark is the grande dame of town, ‘Iao Theater, which opened in 1928 and is listed in the National Registry of Historic Places. It’s home to Maui OnStage community theater productions, which are critically acclaimed; the season runs from October to July.

On the edge of town near Kahului is the world-class Maui Arts & Cultural Center (also called “the MACC”). Since 1994, The Center has served over 250,000 people annually and has enhanced Maui with a national and global profile as a cultural arts destination. For new visitors, returning visitors and part-time residents, at any time of year you can enjoy entertainment by some of Hawaii’s best musical artists or watch authentic hula performances, see an international art exhibit or intriguing exhibition by Maui artists. Often, celebrity entertainers who may not tour larger towns across America stop for a performance at the MACC on their way to or from Asia and the South Pacific. Its newest venue, Yokouchi Family Pavilion, features an outdoor stage with state-of-the-art sound and lighting, a covered dining area with full catering kitchen and built-in bars, and second floor gathering space.

Wailuku and Kahului are only 25 miles from the resort areas of Kaanapali and Wailea.