To the east, beyond Mount Hood, the vastness of Oregon’s geography unfolds. First, golden fields and turbid, salmon-filled rivers. Next, rocky desert canyons and ancient fossil beds. And finally, a snowcapped mountain wilderness larger than Delaware. Pack that car and head east on a classic Oregon odyssey.
Break up the long haul with a pit stop in Pendleton, the state’s rodeo capital. Sidle up and slug back a beer at Prodigal Son Brewery before cruising through the Pendleton Roundup Hall of Fame. Continue on a couple of hours and duck in for dinner at the Lostine Tavern, a cozy, farm-to-table haven housed in a century-old building. Finish the day in nearby Joseph at the Kickstarter-funded Jennings Hotel, remodeled after 100 years with the help of six Oregon artists and designers.
Rise and shine and hop on the Wallowa Lake Tramway, a 4,000-foot gondola that glides high above the glassy, five-mile-long lake to the summit of Mount Howard. Back in Joseph, stop in at Arrowhead Chocolates for a box of small-batch truffles, and picnic with a pint of Extra Special Golden on the lawn outside Terminal Gravity Brewing in Enterprise. Next, head southwest to Prairie City and hitch your wagon at the western-themed Historic Hotel Prairie, with suites facing the Strawberry Mountain Wilderness.
Follow US 26 to John Day’s Kam Wah Chung Museum, a preserved apothecary and general store that served the area’s booming late-19th-century Chinese community. Head northwest to the Thomas Condon Paleontology Center for a brief history of the state’s ancient mammals, and frolic in the Sheep Rock Unit, a rugged landscape of volcanic ash and blue-hued canyons. Drive on to Fossil, and cap off the day’s adventure at Wilson Ranches Retreat Bed & Breakfast with a sunset horseback ride through 9,000 acres of golden juniper.
Your final leg is the showstopper: Head south to the Painted Hills Unit, one of the state’s crown jewels, where a sea of sloping gold-, black-, and red-layered dunes catches stunning morning light. Continue back on US 26 toward Portland, with a pit stop for Smith Rock State Park, where sheer cliffs and spires of basalt create a high-desert playground for sport climbers, hikers, mountain bikers, and trail runners.