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Set 2,000 feet up the slopes of Maui’s Haleakala volcano, Ulupalakua is a truly unique spot on the island.

Here is a place where cattle and elk graze in rolling green pastures, and the island’s only winery—Maui Wine—farms grapes in their ocean view vineyard. It’s a place where paniolo, or Hawaiian cowboys, have wrangled cattle and saddled their horses since the middle of the 19th-century, and where King Kalakaua once wagered Molokini as a late-night gambling bet.

Maui_May_Sun Yat Sen ParkWhen visiting Ulupalakua today, the drive itself is an adventure. It’s a 20-minute, winding drive past small-town Keokea, home to Grandma’s Coffee Shop, three stores, and single gas station. Five minutes in to the drive, the road passes a small park dedicated to Sun Yat Sen—the Chinese revolutionary who lived on Maui while working to found modern China.

After navigating the narrow, twisting road, you’ll notice pasturelands slowly giving way to a grove of towering Eucalyptus, which shade the small but charming Ulupalakua Ranch Store. The perfect place for a hearty lunch, the store has a grill that cooks up delicious meals from meat that’s raised right on the ranch. Order an elk burger and sit on the porch of the classically rustic store, which also has gifts and western-wear with a notable island twist.

Maui_May_UlupalakuaAcross the street is Maui Wine, open daily for free tastings for visitors 21 and older. The winery is especially known for its famed pineapple wine, which has long been an island favorite. More recently, Maui Wine has expanded to also include a variety of grapes. Sip on samples of ranch-grown Malbec, Syrah, and Chenin Blanc, while reading about how the tasting room is set in the cottage where King Kalakaua would stay when he visited the ranch in the late 1800s. You can also peruse the black and white photos of early ranching and farm life, and see how cowboys would drive their cattle to the beach and load them on boats.

Today, the shoreline once used to ship cattle is lined with resorts. And while Makena and Wailea look close enough to touch while standing out on the ranch, there isn’t a public road that runs from the beach up to Ulupalakua. Between the wine, elk, pastures, and views of the southern coastline, this half-day adventure is one of Maui’s most memorable outings.

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