Ranchers, ropers, and Hawaiian cowboys were saddling horses in Maui’s pastures before there was an American West. Cattle were bequeathed to King Kamehameha by early British explorers, and when the King placed a kapu—or law against their harm—feral cattle ran unchecked on the Big Island for over 20 years. In 1832, Kamehameha III summoned three vaqueros from the Mexican state of California, whose mission was to train the Native Hawaiians how to round up wild cattle. The end result was a ranching industry that spread to all of the islands, and the Hawaiian cowboys (known as paniolos) became such talented riders, that in 1904, a paniolo by the name of Ikua Purdy rode entirely unknown into the Cheyenne Frontier Days and rode out as the Steer Roping champion. Today, the long legacy of Hawaii’s ranches lives on through its scenic trail rides, and since ranching, economically, has become increasingly difficult, Maui horseback riding is a way to help save this traditional way of life.
Cool climate, country living, and arguably the best view on Maui—it’s hard to ask for anything more than what you get on this tour. Ride across pastureland to the 6,000 ft. elevation and the border with Polipoli forest, and get an authentic glimpse into Upcountry living on this family-run Keokea ranch.
Before the pineapple and luxury homes, the lush mountainside behind Kapalua was home to Honolua Ranch. Today, Ironwood Ranch has the only trail rides available on the northwest side, although the misty trails through green valleys still remain from days gone by. Ride through an ancient village site on the slopes above Napili, and close the day with a sweeping view of a fiery sunset behind Moloka‘i.
Haleakala Ranch is the real deal: 30,000 acres, over 1,100 cattle, and bi-coastal views you can enjoy from the saddle when riding with Pony Express. Clop across pristine Upcountry pastureland that has been ranched since 1888, and gain access to an exclusive swath of mountainside reserved for real paniolo.
Before Kihei and Wailea existed, Makena was the thriving population center on the island’s southern coast. On a sunset ride with Makena Stables, ride past historic Hawaiian sites that were abandoned in the 1800s, and cross through volcanic pastureland that was the site of Maui’s last eruption. Finish with a walk along the ocean and the sound of waves at sunset.
When the Mendes family relocated to Maui from Portugal’s Azores Islands, they probably didn’t think that 150 years later they’d manage over 3,000 acres. Today, visitors can explore this windswept ranch on the road towards Kahakuloa—and experienced riders are often given the chance to open the horse up and run.