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An Upcountry trip begins in Makawao, an old paniolo (cowboy) town that’s home to the rambling Makawao Steak House, with its framed Hawaiian cowboy-era pictures, and the famed cream puffs at the ramshackle T. Komoda Store & Bakery. But many of the 1920s storefronts now house boutiques and yoga centers, giving the place a hip, bustling coastal vibe. Beyond Makawao, roads narrow to mostly two lanes, passing fields of horses, cattle, or sheep. It can feel like the Texas Hill Country or the Appalachian Mountains, except everything is perpetually green and crisscrossed by drop-it-into-first-gear steep grades.

NextStop and Smell the Flowers