The west-facing upper slope of Haleakala is considered "Upcountry" by locals and is a hidden gem by most accounts. Though this region is responsible for most of Maui’s produce—lettuce, tomatoes, strawberries, sweet Maui onions, and more—it is also home to innovators, renegades, artists, and some of Maui’s most interesting communities. It may not be the Maui of postcards, but some say this is the real Maui and is well worth at least a day or two of exploring.
Upcountry is also fertile ranch land; cowboys still work the fields of the historic 18,000-acre Ulupalakua Ranch and the 30,000-acre Haleakala Ranch. Take an agricultural tour and learn more about the island’s bounty. Lavender and wine are among the offerings. Up here cactus thickets mingle with purple jacaranda, wild hibiscus, and towering eucalyptus trees. Keep an eye out for pueo, Hawaii’s native owl, which hunts these fields during daylight hours.
A drive to Upcountry Maui from Wailea (South Shore) or Kaanapali (West Maui) can be an all-day outing if you take the time to visit Maui’s Winery and the tiny but entertaining town of Makawao. You may want to cut these side trips short and combine your Upcountry tour with a visit to Haleakala National Park. The park is a Maui must-see/do. If you leave early enough to catch the sunrise from the summit of Haleakala, you should have plenty of time to explore the mountain, have lunch in Kula or at Ulupalakua Ranch, and end your day with dinner in Makawao.