Upcountry Maui is fresh mountain air, cool afternoon mists and a scattering of picturesque communities hugging the slopes of a volcano called Haleakala. Upcountry communities reflect an eclectic mix of historic and contemporary influences. Here you'll find a cowboy town, the original Chinese settlement, bedroom communities, a healthy dose of Portuguese culture, a winery, good entertainment and food, art galleries and botanical gardens, downhill biking, ATV tours and horseback riding.
As you head up the mountain on Haleakala Highway (Hwy. 37), watch for towns like Pukalani, Makawao, Kula, Keokea, Hali'imaile and 'Ulupalakua. Makawao is at the hub of Upcountry Maui. Nestled in the hills just off the road to Haleakala National Park, Makawao is the place where pineapple fields give way to tall eucalyptus and jacaranda trees. Here the first paniolos (cowboys) set up shop in the 1800s, when cattle were first introduced to the island. The annual 4th of July parade and rodeo is the big annual event.
Today Makawao reflects the eclectic nature of Maui's diverse and changing nature. The historic building facades and the old hitching post on Baldwin Avenue could be the set of a western movie. But today you're more likely to see bicycle riders than cattle stampeding through the center of town. Hundreds of riders coast down from Haleakala each day on their trip from summit to sea.
More and more, Makawao is shedding its Wild West image to embrace the multi-cultural origins of Maui's newest wave of inhabitants; artists and musicians, spiritual healers, teachers and seekers, alternative health professionals, herbalists, acupuncturists, body workers, naturopathic and holistic physicians.
Keokea is farther up Kula Highway. Originally settled by Chinese immigrants, Keokea remains home to two small stores owned and operated by descendants of these original Chinese families.
Tedeschi Winery, Maui's only vineyard and one of two in the state, is located 2,000 feet up the slopes of Haleakala on 'Ulupalakua Ranch, a 20,000-acre cattle ranch where cowboys still roam. To get to the winery from Central Maui, take Hana Highway (Rte. 36) to Haleakala Highway (Rte. 37). Heading up the mountain, stay on 37 all the way to Keokea. Drive past the Henry Fong Store on the right and continue on the narrow road 5.1 miles to 'Ulupalakua. The winery's tasting room is open daily.
To reach Haleakala National Park, continue on Haleakala Highway, turn left on Crater Road and go to the top. Head uphill again on this road to reach Rice Park, a great place for a picnic with panoramic views of the island. Just past Rice Park, look for Kekaulike Avenue (Hwy. 377) and take a left to find Kula Botanical Gardens, where you can take a rustic nature walk among mature trees and foilage. Enchanting Floral Gardens, across from the 10 mile marker on Highway 37, is another interesting stop.
