Set on the slopes of Haleakala volcano, Makawao is a true paniolo (cowboy) town located in upcountry Maui. Originally settled by ranchers, this small town still retains its western charm. Wooden sidewalks, old horse-hitching posts and false-front buildings make Makawao feel as if you've stepped off an island and onto a John Wayne movie set. Don't let the "wild west" exterior fool you— some of Maui's best shopping resides behind these old wooden storefronts. Charming boutiques, shops, restaurants and art galleries all line Makawao's main drag—you won't find any cheesy t-shirt shops here.
Though a small town, Makawao is known for its art. At Viewpoints Gallery, you can peruse and purchase intriguing paintings and sculptures. Hot Island Glass features ocean-inspired glass-blown art, and even showcases artists while they work. Over at the Randy Jay Braun Gallery, photographs celebrating island life are displayed and sold. If you're looking for a truly unique gift, head over to Maui Hands, which features locally-made crafts, sculptures and jewelry.
Just down the street, supplement your wardrobe with designer clothing from Pink By Nature. The Gecko Trading Company will help you out with island-inspired apparel, and David Sacco's can provide you with the perfect gem to make your hand sparkle. Aching from your shopping spree? Eastern-inspired teas and remedies at the Dragon's Den will cure any of your ailments.
Of course, a stroll down Makawao's Baldwin Avenue will give you many reminders of the town's ranching past (and present). The corner deli and wine shop is aptly named the Rodeo General Store. At Aloha Cowboy down the street, you can buy yourself a fancy belt or sturdy pair of western boots before dining at the Makawao Steak House, which features locally-grown beef.