How, they wonder, is this still Maui, and why haven’t we ever been here? 

At nearly 3,000 feet in elevation, high above the shoreline of resort-lined Wailea and its procession of golden sands, you’ll find Grandma’s Coffee House in Keokea (www.grandmascoffee.com), one of the smallest, oldest and historically rich corners of rural Upcountry Maui. This little-visited region stretches between 2,000 and 4,000 feet on the slopes of Haleakala volcano, and is a place most visitors blow right through en route to their Haleakala sunrise.

Those who take the time to stop, however, will find one of Maui’s most enchanting areas not experienced by nearly enough visitors. Here, in this residential, rural and—dare I say—“real” section of the Valley Isle, you’ll find no resorts or condominiums, and no trace of the beach town atmosphere so prevalent down on the shoreline.

Upcountry was founded by enterprising farmers who were drawn to the fertile slopes. Linton Torbert—founder of what is now the 18,000-acre Ulupalakua Ranch— planted corn and potatoes that were shipped to San Francisco to feed California gold rush prospectors. During the American Civil War, cotton was planted to make up for the deficit in Southern U.S. exports. When Chinese laborers arrived in the late 1800s to work in the valley’s sugar plantations, many used the money they earned to buy land in Kula and farmed their own crops. The Chinese revolutionary Sun Yat Sen spent time here in Keokea on his Brother’s sprawling farm while recouping from multiple failed attempts to overthrow Imperial China. His attempts at revolution would eventually succeed, and a small park a mile past Keokea commemorates his time spent in Upcountry.

Today, both the Chinese history and the agricultural heritage are still very much a part of the area. After breakfast I pull my truck into the driveway of the Ching store, a small grocery store and the only gas station in town. The gas here is often the cheapest on the island, and Florence Ching—a soft-spoken, smiling Chinese woman with a TV playing on the counter—takes my cash and motions toward the pump like she’s been doing for dozens of years.

The next stop is Kula Country Farms (www.kulacountryfarmsmaui.com), a roadside market along Kula Highway that bursts with colorful produce. At this basic trailer full of wicker baskets festooned in shades of green, you can load up on onions and Kula corn, for which the Upcountry region is famous. When strawberries are in season, you can pick your own from the fields next to the trailer. The fall pumpkin patch in September and October is backed by an ocean view.

While the Kula soil has been producing bountifully since the middle of the 1800s, it’s only recently that the agricultural charm has been blended with bits of tourism. 

One of the most striking and romantic examples of the fusion is found at O’o Farm (www.oofarm.com), an 8.5-acre, sustainably managed farm that supplies produce for Pacific’o Restaurant. For Maui farmers, providing produce for island restaurants isn’t anything out of the ordinary, but O’o Farm actually invites visitors to the property for a hands-on farm tour and luncheon. 

The farm is open only Monday through Thursday. The last time I visited I helped pick spinach to accompany our lunchtime salad and tasted fresh crops such as watercress and creamy, fleshy cherimoya. Even with the tour beginning at 10:30 a.m., the mists rolling across the 3,500- foot elevation warranted a light jacket or sweater, and freshly roasted coffee that is grown on the farm was offered to combat the chill. The luncheon setting was a long wooden table beneath a wildvine- covered trellis, and the squawk of chickens and distant pheasant provided an authentic and natural soundtrack. Coffee was served in a large French press, visitors were encouraged to bring their own wine, and you couldn’t shake the feel of a luxurious picnic in your own secret villa on the mountain. 

Maui’s Winery, Ulupalakua Vineyards, the Island’s only winery, is located at historic Ulupalakua Ranch, 20 minutes past Keokea, and I make the decision to go for a drive through the green of the rolling pastures (www.mauiwine.com). I weave past snarling, stone-frozen lions that seem to leap from Sun Yat Sen Park. Although it’s only five miles from Keokea to the winery in Ulupalakua, the narrow road undulates like a country roller coaster with a sweeping, panoramic view. Down below, along the distant shoreline, the splashing of humpback whales can be discerned even from this altitude, and Molokini Crater looks like nothing more than a crescent moon in the sea.

By the time I’m greeted by the camphor and kauri trees, which tower above Tedeschi’s tasting room, I’ve realized the view O’o Farm / Photography credit: Joia Holman alone is worth the drive. Inside the tasting room—itself a historic 19th-century cottage where King David Kalakaua, Hawaii’s last reigning king, would hold parties of legendary repute—a sleek wooden bar runs the length of a room packed with bottles of ranch-produced wine. Though the vineyard began in 1974 by making sparkling wine from pineapples, seven varietals of red and white grapes are grown on the ranch today. Ulupalakua Red, one of the most popular blends, is a combination of Merlot, Syrah and Malbec, with hints of white pepper and vanilla. Upcountry Gold mixes Viognier and Muscat with classic Chardonnay. The winery is completely unpretentious and intriguingly historic, and walking the grounds feels like touring a museum that just happens to also serve wine. And despite being only a few miles from the ocean as the crow flies down toward Makena, the pastoral setting is reminiscent of outposts you might find in the American West.

Across the road from the winery tasting room, puffs of smoke from a carnivorous grill rise into the open blue sky. In addition to cowboy memorabilia, the Ulupalakua Store is famous for elk burgers from the local herd of elk. Yes, you read that right: elk. In Maui.

What’s more, all the meat served off the Ulupalakua grill—whether it’s elk from the pastures, Maui Cattle Company beef brisket or lamb served with Kula greens and onions—is from livestock raised on Maui and fed by Haleakala’s grass. And there are burgers for vegetarians, made from Maui-grown taro. At a shaded picnic table beneath a rustling eucalyptus, dining at the store is like a century-old throwback to the pioneering ranchers of old.

If you keep driving south from Ulupalakua, it doesn’t take long for civilization to disappear into the arid grasslands. Thus begins the famous “back road” to Hana, although that is a separate adventure for another day of exploring this beautiful island. 

Instead, I drive back along the roller- coaster highway on a path for the town of Makawao. As you hang a right onto Haleakala Highway (Route 37) just prior to Kula Country Farms, the road climbs higher past botanical gardens and dreamworthy country homes.

Past the turnoff for Crater Road and the route to Haleakala Crater, two of Upcountry’s most notable lodgings—Kula Sandalwoods (www.kulasandalwoods.com) and Kula Lodge (www.kulalodge.com)—occupy opposing sides of the road and appear as rustic and romantic as ever. Even though Upcountry doesn’t boast any resorts, there are still a number of small inns and lodges where serenity replaces activity. Concierges are swapped for affable innkeepers who’ve lived here for 30 years, and the swimming pool is traded for a roaring fireplace to add warmth to the winter nights. As I descend toward Makawao, I see a field full of horse trailers and diesel trucks gathered for an afternoon at the polo fields. The arena sits on Haleakala Ranch, a 30,000-acre property that’s home to 4,000 head of cattle, and for the paniolo (Hawaiian cowboys) who run the ranch and manage the operations, roping, riding and rodeo sports are still a way of life. It’s an island existence that runs completely counter to the tourism-based hustle of the coastline, where traditions rooted in generations of ranching eclipse timeshares or discount luaus.

Finally, past the Oskie Rice Roping Arena and stands of violet jacaranda, I pull up to the timeless center of Makawao, a “one stop sign” kind of town that is equal parts artsy and Western. The hitching posts lining Old West storefronts are a throwback to the ranching town of the past, and while it’s technically still possible to find townsfolk on horseback, nowadays you’re more likely to find new age yogis and hippies kicking beanbags on the sidewalk. It’s this eclectic charm that gives Makawao its spunk, and the shopping along the town’s main drag is a reflection of its singular character. Clothing boutiques with the trendiest fashions sit next to medicinal herb and tea shops, and high-end art galleries and Tahitian pearl jewelers border spice shops, glassblowers and a family-run bakery that has been curing Makawao’s cream puff craving since its doors opened in 1916. 

Standing at the only intersection in town, I follow the directions to Polli’s Mexican Restaurant (www.pollismexicanrestaurant.com), where the sign out front reads “Come In and Eat or We’ll Both Starve!” Surfing videos splash across a television that is draped in a colorful blanket, and photography and artwork from across Latin America create an authentic, festive decor. Most of the bar patrons know each other by name, and with waitresses who’ve been working here for nearly 25 years, it’s a testament to the intoxicating staying power of Upcountry’s community lifestyle.

After a juicy fish taco and a mango margarita, the 10-minute drive to the town of Pa’ia brings me back to sea level and the beach. While the pink sunset over soft white sands is a familiar Maui tableau, it’s the emerald green pastures and hickory brown fence posts, ripe red tomatoes and violet jacarandas, and the colorful spirit of the Upcountry community that define this rural corner of paradise that is all too often overlooked.