This historic, off-beat Maui town is laden with ‘ono bakeries, quirky shops and showstopping murals.
Once an easy-to-miss sleepy town, Wailuku is experiencing a contemporary renaissance – with funky boutiques, craft cocktail bars and larger-than-life murals popping up left and right.
Despite the new age wave sweeping this Central Maui town, some of the best things about Wailuku have been around for generations. Explore the intersection of old and new on Wailuku’s eclectic streets with our curated Wailuku walking guide.
SixtyTwo MarcKet
A proper feed is essential before exploring Wailuku on foot. Tuck into heaping plates of eggs benedict, quiche or crepes at SixtyTwo MarcKet, a farm-to-table eatery that highlights seasonal ingredients. Chef-owner Marc McDowell rotates the menu every 62 days and often features specials with ingredients harvested the very same day.
Beyond the menu, SixtyTwo MarcKet is a veritable market featuring a selection of spices, sauces and rubs made with local herbs.
Four Sisters Bakery
Don’t fill up too much at breakfast — because your next stop is Four Sisters Bakery, a Wailuku staple since 1983.
Around the corner, on E Vineyard Street, look for a pale yellow storefront with a fading sign. Although unassuming from the outside, Four Sisters pastries are a big deal – evidenced by the line that often stretches out the door. Pick up a few loaves of banana bread, cream-filled malasadas and famous melt-in-your-mouth butter rolls.
Market Street
After securing the Four Sisters’ goods (and stopping at the car to drop them off), return to Market Street – the beating heart of Wailuku Town.
The balance of old and new is evident here. Buzzy bars, locally-owned boutiques and trendy cafes stand alongside antique shops and music stores stocked with vinyl records. History buffs can ogle at Maui’s oldest operating theater, ‘Iao Theater, first opened in 1928, while lovers of all things old-school can browse thousands of LPs in Request Music’s basement.
Meanwhile, contemporary shoppers can peruse the island-inspired garb at Brown Eyed Bella before stopping into Depo Market, a jewelry store that provides job opportunities to adults with disabilities.
However, no exploration of Market Street is complete without getting a feel for Wailuku’s artistic undercurrent. Drop into Sabado Art Gallery for a selection of Hawaiian art and prints or Sandell Artworks for trippy t-shirts and whimsical prints. Across the street, ParadiseNow features Maui-meets-vintage artworks and locally-designed aloha wear.
Main Street
While Market Street has long been the place to be in Wailuku, Main Street is at the center of the town’s revival.
Main Street’s once-vacant storefronts are becoming second-hand boutiques, metaphysical shops and zero-waste stores. Food truck hubs are replacing used car lots – and rumor has it that a retro tavern is set to open on Main Street in summer 2024.
Among the eclectic storefronts, Native Intelligence is a must-visit. This cultural boutique is filled with Hawaiian products made by local artisans and creatives—from clothing and jewelry to handmade sennit and lei hulu (feather lei). Native Intelligence is also known for its vibrant fresh flower lei selection.
Shikeda Bento Patisserie
Head mauka (uphill) on Main Street to a special hidden gem – Shikeda Bento Patisserie. The short walk to Shikeda allows you to admire some of Wailuku’s larger-than-life murals. These works are part of a public art project, and each incorporates ʻōlelo no‘eau, or Hawaiian proverbs.
But the real treat lies at a bona-fide hole-in-the-wall in the Main Street Promenade food court. Shikeda Bento Patisserie offers, you guessed it, bentos and Japanese and French-inspired pastries. Pick up an ube mont blanc, lilikoi toffee puff or classic cream puff. You’ll need the pick-me-up to make it to the next stop.
Maui Historical Society
Next, make the ten-minute uphill walk to Hale Ho‘ike‘ike at the Bailey House, home to the largest public collection of Hawaiian artifacts in Maui County.
Historical points of interest abound before you even reach the museum. Near the corner of High Street and Main, you’ll spot the Old Wailuku Courthouse, built in 1907, two years after Wailuku was named the county seat of Maui.
Across the street stands the historic Ka‘ahumanu Church, first established in a meager shed in 1832. Queen Ka‘ahumanu attended a service that same year and requested that a more permanent structure be named after her. Her request was honored, and the present building was constructed in 1876.
At last, Hale Ho‘ike‘ike at the Bailey House Museum offers a captivating look at Maui’s past. Once the site of the Royal Compound of Kahekili, this historic building, constructed in 1833, now serves as a museum brimming with fascinating artifacts and exhibits. Explore an array of Hawaiian artifacts, including traditional tools, household items, and an impressive collection of 19th-century paintings by Edward Bailey — missionary teacher, plantation owner and the house’s namesake.
Ester’s Fair Prospect
Your final stop is a deserved one. Cozy up at the lively tropical cocktail bar, Ester’s Fair Prospect, for craft libations and small bites. The cocktail list favors locally-sourced ingredients – like calamansi and Maui-grown sugarcane – as well as niche spirits like okolehao, cachaca and apple jack.
Grab a seat on the outdoor patio and soak in views of ‘Iao Valley, or take a chair at the bar. Ester’s is always abuzz with visitors and residents, so strike up a conversation with your neighbor. You might get the inside scoop about the next must-visit place in Wailuku.
