21 Things to Do in Makawao

Aloha from My Upcountry Home

Every time I drive into Makawao, the first thing I notice is the air, it's cooler, scented with eucalyptus and the faint, sweet promise of fresh malasadas from Komoda's. As a long-time Upcountry resident, this isn't just a stop on a map for me; it's the heart of a community that holds two of Maui's most precious stories in its hands. It's a place where the weathered wooden storefronts seem to whisper tales of the past, while the vibrant colors spilling out of art galleries sing of the present.

Makawao is a town of beautiful contradictions. It's where you'll see a real-life paniolo, or Hawaiian cowboy, in boots and a wide-brimmed hat walking past a chic boutique showcasing the latest in sustainable island fashion. It's where the rugged, independent spirit of Maui's ranching history meets a thriving, world-class arts community. This unique intersection of grit and grace, of history and creativity, is what makes Makawao one of the most soulful and fascinating places in all of Hawaiʻi.

The Soul of the Paniolo: The Enduring Legacy of the Hawaiian Cowboy

To truly understand Makawao, you have to start with the paniolo. Long before the iconic cowboys of the American West were driving cattle across the plains, Hawaiian cowboys were navigating the rugged volcanic slopes of the islands, creating a rich and unique culture that defines Upcountry Maui to this day.

From Royal Gifts to Ranging Herds: The Dawn of Cattle in Hawaiʻi

The story begins not with a cowboy, but with a king and a gift. In 1793, British Captain George Vancouver presented King Kamehameha I with six cows and a bull. Recognizing their potential, Kamehameha placed a royal kapu, or sacred prohibition, on the animals, forbidding anyone from harming them. This act of foresight allowed the herd to grow exponentially. Within a few decades, thousands of wild cattle, known as pipi ʻāhiu, roamed the islands. They became a formidable, and often dangerous, presence, rampaging through villages, destroying crops, and even eating the thatch from the roofs of homes.

The Arrival of the Vaqueros and the Birth of the "Paniolo"

By the 1830s, the cattle population had become unmanageable. King Kamehameha III needed a solution. Hearing of the legendary horsemen of California, he sent one of his high chiefs to recruit experts who could teach his people how to handle the wild herds. The men who arrived were not the "Spanish" cowboys of popular lore, but skilled Mexican vaqueros of mixed heritage, masters of roping and riding.

The Hawaiians, natural horsemen themselves, quickly adapted the vaqueros' techniques. They learned to braid their own rawhide lariats, called kaula ʻili, and became masters of working cattle on the challenging island terrain. They called these new cowboys paniolo, a Hawaiian phonetic rendering of Español, the language the vaqueros spoke. This was more than just an exchange of skills; it was the birth of a new culture. The paniolo tradition became a profound example of ethnogenesis, where two cultures merged to create something entirely new and distinctly Hawaiian. This fusion even influenced Hawaiian music, as the vaqueros' guitars were adopted and adapted into the singular Hawaiian style of open-tuning known as kī hōʻalu, or slack-key guitar, its portability perfectly suited to the paniolo lifestyle.

Maui's Ranching Legends and a World Champion

As ranching expanded across the islands, Upcountry Maui, with its wide-open fields, became a major hub. Great ranches like ʻUlupalakua Ranch were established, and generations of paniolo families honed their skills on the slopes of Haleakalā. Among these legendary figures, one stands tallest: Ikua Purdy.

In 1908, Purdy, a foreman from ʻUlupalakua Ranch, traveled with two other Hawaiian cowboys to the biggest rodeo in the country, Frontier Days in Cheyenne, Wyoming. The mainland competitors, who had never seen anything like these cowboys with their flower lei-adorned hats, were dismissive. But Purdy stunned the crowd of 30,000, winning the world steer-roping championship in a breathtaking 56 seconds. This victory was more than just a trophy. It came at a time of immense political and cultural change in Hawaiʻi, following the overthrow of the monarchy. Purdy's win on a national stage became a powerful symbol of Hawaiian excellence, skill, and resilience, bringing a tremendous sense of pride back to the islands that endures to this day. Other notable Maui paniolo families, such as the Hapakuka and von Tempsky families, also left their mark, cementing the legacy of ranching in the region.