A walk down Wailuku’s quaint Market Street might feel like a stroll through the 1950s, but the town’s history goes back much further. Kamehameha I won a decisive battle here in 1790; missionaries arrived in the 1800s; and by 1860, the Wailuku Sugar Company had turned the village into a bustling plantation town.
Built in 1928, the ‘Iao Theater once hosted Bob Hope and Frank Sinatra. Today, Wailuku’s pink landmark stages community theater productions and Maui Chamber Orchestra concerts. 68 N. Market Street. 808-242-6969; mauionstage.com.
Along with items from the missionary period and Hawai‘i’s aristocracy, Hale Ho‘ike‘ike at the Bailey House exhibits precontact Hawaiian artifacts and the Islands’ largest collection of Hawaiian land snails. 2375-A Main Street. 808-244-3326; mauimuseum.org.
Maui isn’t known for its nightlife, but Wailuku stays out later for First Friday, a monthly street party with live music, food trucks, and after-hours shopping. mauifridays.com.
Upbeat island-inspired designs emblazon Maui Thing T-shirts, hats, and accessories. 7 N. Market Street. 808-249-0215; mauithing.com.
Find work by kapa makers, feather artists, and other Hawaiiana practitioners at Native Intelligence, which also carries locally made items inspired by Polynesian culture and native species. 1980 Main Street. 808-249-2421; native-intel.com.
The basement of Request Music holds an extensive collection of new and used LPs. This independent store hosts performances and stocks CDs, comics, movies, and vintage posters. 10 N. Market Street. 808-244-9315; fb.com/requestshawaii.
Thin-crust pizzas from a recipe passed down by the owner’s Italian grandmother are undeniable, but Giannotto’s Pizza also serves traditional pastas and subs. 2050 Main Street. 808-244-8282; giannottospizza.com.
At the nondescript neighborhood favorite Ichiban Okazuya (very limited parking, carry-out only), chicken katsu leads a lineup of plate-lunch classics. 2133 Kaohu Street. 808-244-7276; tinyurl.com/ichibano.
808 on Main has a full menu of salads, burgers, and sandwiches. For pau hana, the Maker’s Smash combines Maker’s Mark bourbon, lemon juice, simple syrup, bitters, fresh mint, and soda water. 2051 Main Street. 808-242-1111; 808onmain.com.