Discover Maui’s Hidden Gems: A Scenic Road Trip Through Upcountry

Away from the beachfront resorts, Maui’s inland—called the Upcountry—often overlooked, offers alluring boutiques, restaurants, and places to stay.

Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket list adventure.

Malu Manu is arguably Maui’s most magnificent lookout. At this 1920s log cabin rental, set 4,000 feet up on the west-facing slopes of the Haleakala volcano, guests can gaze down upon the island’s northern and western coasts, as well as the craggy ridges of the West Maui Mountains. On my first night there, the weather was chilly enough to warrant putting on a puffy jacket and throwing kiawe wood in the cabin’s stone fireplace. That evening, a welcome book revealed that the name, malu manu, means “sanctuary of birds” in the Hawaiian language. The moniker rang true the next morning when a symphony of birdsong from endemic species such as apapane and amakihi wakened me to a pastel sunrise.

Golden beaches and cerulean sea lured me to Maui 15 years ago, but in those early days, the interior regions—collectively referred to as Upcountry—seemed nothing more than a backdrop to coastal sun and surf.

Like most tourists, I initially saw the misty mountains and electric-green pastures as views to be admired, worth little more attention than a day trip tacked onto a stay in the manicured beach resorts of Wailea or Kaanapali. If you watched the sunrise from the moonlike summit of Haleakala; visited the lavender farm, winery, and dairy in Kula; and browsed the galleries of Makawao, you felt you had “seen” Upcountry.

However, as my annual trips to the island stretched from weeks to months, I was drawn inward. Far from the plumy palms and turtle-dotted shores, I found a vibrant landscape of purple-flowered jacarandas, native sandalwood, coiled hapuu ferns, and verdant ranchland.

Small Upcountry towns were rich with history yet far from stuck in the past. Old pineapple canneries had been transformed into restaurants and boutiques. Farmers and makers were updating native traditions and celebrating local goods. These communities thrived creatively not for the visitors but for the people who call the island home.

3 Ways to Experience Maui’s Magic Without the Crowds

One such Upcountry resident is Hawaii-born Clifton Dodge, a third-generation steward of the land where Malu Manu sits. A biodynamic horticulturist, he and his wife, Reba, a florist and flower farmer, live next door and are responsible for the brilliant blooms outside the cabin door: cotton-candy-colored king protea, straight out of the Jurassic era; spiky red and yellow pincushions.

The couple plans to offer agricultural tours and garden-to-table feasts. As hosts of Malu Manu, they direct guests to the hidden gems in Kula, the nearby town. These include Maui Bees, a farm and market that offers tours and beekeeping workshops, selling house-made focaccia, farm-fresh produce, and seasonal honeys.

The land surrounding Manu Malu once belonged to Maui sugar plantation magnate Joseph Cooke and his wife, Maud, the daughter of congressman and sugar plantation manager Henry Baldwin. The couple was married half an hour from the mountainside cabin at the legendary Baldwin Estate in Haiku, a 20-acre property privately owned by notable islanders since its first deed in 1849.

For years, I assumed the whitewashed home with its dramatic palm-lined driveway and sweeping veranda was so grand it could only belong to Oprah, a part-time Maui resident (she actually lives in Kula).

However, last spring, the current owners, Maui photographer Erica Chan and her Vancouver-based family, reimagined the nine-bedroom residence—now known as Haiku House—as a luxury rental. I spent hours wandering the grounds, which feel like a tropical arboretum, with centuries-old monkeypods and figs, plus an organic garden and citrus orchards.

Inside the home, native koa wood floors, vintage floral wallpaper, and framed sheet music for island folk songs ooze Hawaiiana. For a moment, I was transported to the 1890s, when the Baldwins hosted Queen Liliuokalani at parties here.

A mile up the road from this gated paradise is Colleen’s at the Cannery, a Haiku institution opened by Colleen Nicholas in 1996. “At the time, I’d be lucky if two cars drove by,” Nicholas said of the restaurant’s early days. “Haiku felt like a hideout from the hustle.”

Her friends questioned why she didn’t open her business in the hip town of Paia, but Nicholas foresaw how artists would be pushed out of what has since become a bucket-list tourist stop on Maui’s North Shore. “Today we call it Pahaina,” she said, a jab at the surf town’s transformation into a drag of pricey souvenir shops resembling touristy Lahaina.

What Nicholas envisioned as a local hangout is still going strong, serving three meals a day. Last September, she converted an adjacent space into a chic bar that wouldn’t be out of place in Honolulu’s hip Chinatown, featuring bold tropical wallpaper, craft cocktails, and late hours.

“When people come to Maui, I want them not only to see the beauty of our local plants but also to feel the mana—the energy—of the place I call home.”

“It was a rebirth of sorts,” Nicholas said. “I sensed the community wanted a place like this. I know I did.” The staying power of Colleen’s paved the way for other businesses to take root across the street, including sushi spot Nuka and Toohey’s Butchery & Bistro, a discerning eatery that hosts live music on its patio.

Ten minutes north, the tropical jungles of Haiku give way to the cowboy country of Makawao. Paniolos—Hawaiian cowboys—settled this area in the 1800s, and the local roping club still hosts Hawaii’s biggest rodeo of the year. In the late 1990s, the town’s quarter-mile-long main street became known for its galleries; more recently, indie boutiques like Driftwood, Tribe, and Holoholo Surf have become showcases for the island’s most talented jewelers, designers, and craftspeople.

No store embodies the local maker ethos better than Monarch Collective, opened last July by jewelers and friends Perri Ricci and Nickoel Martyn.

“We were originally looking for a space in Paia because of the foot traffic, but the shops Upcountry felt more geared toward locals,” Ricci said. “Everything around here is more specialized and has a story behind it.”

The shop’s pegboard walls display Ricci’s gold-accented bangles, made with puka shells she collects on neighboring islands, and Martyn’s watermelon-tourmaline necklaces, as well as pieces from 20 other Hawaii artists, including printmaker Susanna Cromwell and silk dyer Jennifer Miller. Most of the artists work a shift in the store, and regular events, like a pop-up pearl bar where clients can help design their own necklaces, allow visitors to interact with the makers.

That connection with customers leads to education, said Lauren Shearer, the Maui-born founder of Hawaii Flora & Fauna. In her jewel box of a studio in Haliimaile, a small town five minutes north of Makawao, Shearer crafts modern versions of traditional lei from foraged finds like blue jade, ficus berries, and pikake buds, a favorite of Princess Kaiulani, the last heir to the Hawaiian throne.

“The ubiquitous purple-orchid lei bestowed upon visitors as a sign of welcome isn’t even traditionally Hawaiian,” Shearer lamented. “The flowers are scentless and shipped in from Thailand.”

Shearer’s studio could double as a natural history museum. Its shelves are lined with giant lobster claws, spiny skeletons of puffer fish, and vintage glass jars filled with tiny puka shells. When I stopped by one weekend, I found her head down, face hidden behind her long dark locks, patiently weaving silvery-gray strands of Pele’s hair—Spanish moss—and violet-hued crown flowers into a lei popo, or flower crown. Her workshop table is piled high with shiny lime-green seedpods, coconut flower buds, and clusters of rosy hee berries.

In her quest to expand beyond custom orders, which can take up to seven hours per lei, Shearer, along with friend Beth Elliott, reimagined an old gas station into a store last December, called the Haliimaile Filling Station. “At first glance, it looks like a Midwest truck stop,” she joked. “You half expect tumbleweeds to roll past.”

For decades, visitors came to this town only to dine at Haliimaile General Store, chef Bev Gannon’s pioneering farm-to-table restaurant, or to tour the adjacent pineapple farm. However, the Filling Station has become a magnet. A boutique, gallery, and gathering space of sorts, the shop sells Shearer’s lei but also the colorful, dreamlike landscape paintings of local artist Jennifer Valenzuela and bangles and hoops decorated with conch and coral from jeweler Bella Resta, who sources her wares exclusively in Paris and Maui.

Before the pandemic hit, the shop had emerged as a community hub thanks to a roster of events, including a club and workshops on various subjects from crystal-sage bundles to orchid care. As with many businesses, its future is uncertain, but Shearer is determined to continue her work.

“My mission is to share knowledge,” she said. “When people come to Maui, I want them not only to see the beauty of our local plants but also to feel the mana—the energy—of the place I call home.”

How to See Upcountry Maui

Where to Stay

For couples, the one-bedroom Malu Manu (cabin from $225) offers cozy cabin digs and killer views.

For groups, the exclusive-use Haiku House (villa from $6,500) has nine bedrooms, lovely grounds, and a concierge team to book excursions.

Where to Eat

In Haiku, Colleen’s at the Cannery (entrées $19–$30) serves unfussy basics all day long.

Sushi spot Nuka (entrées $14–$28) sources locally and mills rice in-house.

The burgers at Toohey’s Butchery & Bistro (entrées $7–$20) are legendary—after lunch, visit the butcher and buy something to cook for dinner.

Hawaiian produce, meat, and fish have been the focus at Haliimaile General Store (entrées $30–$46) since it opened in 1987.

Where to Shop

Head to Maui Bees in Kula for honey, farm tours, and workshops.

Driftwood, in Makawao, sells women’s wear and home goods with an easygoing vibe. Nearby, find hippie-with-an-edge apparel at Tribe.

Holoholo Surf stocks swimwear designed by owner Julie Stone and colorful longboards from Manuela Shapes.

Monarch Collective showcases work by local artists.

The lei at sister shops Hawaii Flora & Fauna and Haliimaile Filling Station are made with materials that nod to the history of the craft.

How to Travel

Hawaii specialist Marilyn Clark (marilyn@lighthousetravel.net; 844-339-1774), a member of iBestTravel’s A-List of top travel advisors, can organize an itinerary that includes Upcountry Maui.

A version of this story first appeared in the October 2020 issue of iBestTravel under the headline Maui: Upcountry Magic.