When people think of Maui, they often imagine beaches, palm trees, and waves – but there’s a whole other side to this tropical paradise. Head up to Maui’s Upcountry, where rolling hills, sprawling ranch lands, and crisp, cooler air bring a different kind of island experience. This area, including the town of Makawao, is the heart of Maui’s cowboy, or “paniolo,” culture, giving visitors a surprising taste of Hawaii’s lesser-known ranching heritage.
The paniolo tradition dates back to the early 1800s when King Kamehameha III invited Mexican vaqueros (cowboys) to train locals in cattle handling. These skilled horsemen introduced not only ranching but also the aloha version of cowboy culture, leading to a unique fusion of Hawaiian and Western lifestyles. Today, that spirit lives on in Makawao, known for its old-time charm and a thriving artist community, making it a hub for both history buffs and creatives.
Walking down Baldwin Avenue in Makawao feels like stepping back in time. Wooden storefronts house quirky boutiques, art galleries, and local food spots. Stop by Komoda Store and Bakery, a legendary spot for pastries.
The annual Makawao Rodeo, held each July, is one of Hawaii’s most popular rodeos and a perfect event for those curious to see Hawaiian cowboy culture in action. From roping competitions to live music and parades, the rodeo draws locals and visitors alike.
For those looking to explore more than just beaches, Upcountry Maui offers a beautiful blend of history, culture, and rugged outdoor adventure that showcases Hawaii’s diverse heritage.
An upcountry roadtrip to the town of Makawao is a half day adventure. The drive from Kihei is about 35-40 minutes. Take a shopping stroll down the main road or chill for a while at a coffee shop. There is something for everyone in this cowboy town.
