Skip the Beach for a Day: Maui’s Hidden Cowboy Town Is Worth the Drive

On the northwestern slopes of Haleakalā, an active shield volcano in Upcountry Maui, you’ll find the small town of Makawao, where Hawaiian paniolo (cowboy) culture reigns supreme and the vibe is laid-back and local. Ranching in the early 19th century brought paniolo (cowboy) culture to Maui after King Kamehameha III invited Mexican vaqueros to Hawaii to teach the local Hawaiians about herding, roping, and rodeo events. The traditions live on with the annual Makawao Stampede, Maui’s favorite rodeo celebrated every Fourth of July weekend. 

Drive down Baldwin and Makawao avenues in town and you’ll spot century-old, plantation-style buildings that still house businesses today. This main area of town is where sugar plantation workers and cattlemen often joined for a sense of community, whether it was at the post office or over a cup of coffee. The false fronts on the stores were designed to project an image of stability—a technique used across the American West that adds to Makawao’s western vibe.

Today, art galleries, distillery tours, and the annual Makawao Stampede (Hawaii’s largest paniolo competition), all give visitors a perspective that’s different from Maui’s traditional beach scene. The town also gives visitors a deeper understanding of Maui’s varied terrain, where lush upland fields, mountainous views, and cooler temperatures showcase the sand-free side of the island. After a day or two at the beach, take a drive north for a less-explored Maui locale. 

Throughout the main drag of town you’ll find art galleries specializing in sculptures, paintings, jewelry, and glassworks. Watch artist Chris Richards work with molten glass to create dreamy jellyfish sculptures at Hot Island Glass, and find various scenes from Maui painted by Jordanne Perkins at Jordanne Gallery. Vibrant Hawaiian landscapes and marine life are found on canvas at Sherri Reeve Gallery, and fine art from an array of Hawaiian-based artists are found at Viewpoints Gallery. Just down the road, Hui No’eau Visual Arts Center offers art classes in metalsmithing, watercolor, screenprinting, and even botched artwork, where you create a masterpiece from something that didn’t quite work out the first time. 

Traditionally held over Fourth of July weekend, the Makawao Stampede is a three-day rodeo extravaganza that’s become one of the premier events across Maui. See paniolos try their hand at po’o wai u, a Hawaiian style of cattle roping not seen anywhere else in the world, plus more than 300 competitors in bull riding, barrel racing, double mugging, team and tie-down roping, and more. Family-friendly activities also include face painting and bounce houses. 

Makawao’s milder temperatures and consistent rainfall create an ideal environment for growing blue agave, and at Waikulu Distillery, you can see just what lush volcanic soils do to help these plants thrive. Take a tour of the agave farm and distillery, where you’ll walk through the agave fields and then see the handmade copper still and other equipment used to create the spirit. Tours end with a tasting of Waikulu’s spirits. 

Maui has a deep history with the pineapple. The fruit was growing wild in Maui by the 1820s, and by the early 20th century, the Maui Pineapple Company was in full swing. In Hali’imaile, a small town near Makawao, Maui Pineapple Tour offers visitors the chance to see a working pineapple farm plus learn about cultivation and the fruit’s history on Maui. Tours with lunch and dinner are available as well, and each guest takes home a Maui Gold pineapple as part of the experience. 

Rising over 10,000 feet above sea level, Haleakalā is a dormant volcano where you’ll see arguably the best sunrise of your life. Watching the sun rise from the volcano’s crater is an experience that Mark Twain called “the most sublime spectacle I have ever witnessed,” and reservations are required. Legend says that the demigod Maui wrangled the sun as he stood on the volcano’s summit, slowing its descent to make the day last longer. While you’re here, explore more of the park’s 30,000 acres full of hiking trails and endangered species like the nēnē (Hawaiian goose). 

For more than 100 years, the Komoda family has been blessing Makawao with a gathering place where food and community are the priority. They’re known for their to-die-for pastries, which often sell out before noon. The cream puffs are the most popular item, but you should also try their stick donuts, guava malasadas (a Portuguese donut), and long johns and butter rolls. There’s also pies, cookies, danishes, tarts, and so much more. The store is closed on Wednesdays and Sundays, so plan accordingly. 

Have an alfresco breakfast or lunch at Freshies, where a large tree in the courtyard provides plenty of shade. The menu features traditional breakfast dishes like omelets and French toast, plus fresh salads, tacos, burgers, and fresh fish for lunch. 

Since the mid ‘80s, Casanova has brought Italian flavor to Makawao. Order a pizza for the table, as Casanova uses an Italian wood-fired oven to make Napoli-style pies with keawe wood from Haleakalā Ranch. Pastas are made in house, and the homemade focaccia bread is great for sopping up sauces. 

Mitzi Toro started baking cookies in 2012 as a fundraiser and was encouraged to turn her efforts into a full-blown Maui cookie empire. She did just that by starting The Maui Cookie Lady, and you can find her delicious creations right on Baldwin Avenue. Mitzi uses Hawaii ingredients as often as possible, including Maui Gold pineapple, Waihe’e Valley macadamia nuts, rum from Kōloa Rum Company, lilikoi from Haiku, caramel from Haleakalā Creamery, and more. The white chunk mac (white chocolate macadamia nut) is a bestseller, and the lilikoi white chocolate is something you’ll find only in Hawaii. For a real Maui treat, try the Anuhea Upcountry Breeze cookie: Ali’i Kula Lavender Farms lavender, Waihe’e Farms macadamia nuts, island-grown calamansi (Filipino lemon), white chocolate truffle, Hawaiian sea salt, and a lemon-meringue reduction drizzle. 

For fresh sushi, check out Satori, a sushi food truck serving local fish and other dishes using ingredients from local farms. The lilikoi spicy tuna roll is a hit, with macadamia nuts adding crunch and a zippy lilikoi aioli you won’t find anywhere else. They also serve sushi bowls. Ramen, and poke bowls.  

Also along Baldwin Avenue, Makawao Public House has an extensive menu with dishes nodding to the town’s paniolo history. There’s the paniolo pie, made with local venison, beef short ribs, uala (Hawaiian sweet potato), carrots, onion, and mashed potato, and the Japanese-style steak—a nod to the island’s Japanese history with wasabi, ponzu, and furikake. Smash burgers and birria ramen are sure to fill up any cowboy, and a lengthy cocktail menu means you have to come back for a taste of it all. 

Just outside of town, Lumeria Maui offers 24 guest rooms offering gorgeous garden or ocean views. The property is designed for retreats, whether you’re a solo traveler or with a group looking for an Upcountry experience that’s different from anything you’ll find at the beach. Walk the lush garden spaces for zen moments, and take classes in meditation, yoga, hula, lei making, and much more. The on-site restaurant, The Wooden Crate at Lumeria, is an experience in itself, where Maui-grown produce are highlighted and fresh meats and fish from Maui’s shoreline and ranches create healthy, balanced plates.