written by Jen Stevenson
In historic Pendleton, home to one of the country’s most famous rodeos every September, grab a bite at busy Sister’s Café before embarking on the entertaining 90-minute Pendleton Underground Tour. Try a pint of Righteous Indignation red ale at Prodigal Son Brewery and Pub, or pair wood-fired pizza with one of the beaker- bound house cocktails at Oregon Grain Growers Brand Distillery, then head a mile east to the Pendleton Woolen Mill, which offers four free weekday tours, no reservations necessary. In La Grande, sip Walla Walla rosé at charmingly renovated Wine Down café and wine bar, then eat 6 Ranch grass-fed beef burgers and smoked aioli-drizzled dirty fries alongside the local college kids at Side A Brewing, set inside the historic La Grande Firehouse, just off the main drag.
EAT + DRINK
Brake for Oregon berry shakes and Clown Cones at Wallowa’s delightfully old-fashioned Little Bear Drive-In, then shop everything from local seasonal produce to hand-carved apple heads at eclectic, century-old M. Crow & Co. general store in nearby Lostine. Ten minutes southeast, stock up on red raspberry seed oil and citrus sunrise body butter at Wild Carrot Herbals in downtown Enterprise, then claim a table in the grassy creekside garden at Terminal Gravity Brewery and Pub and tuck into brews and buffalo burgers. In small but mighty Joseph, stroll the cheerful main street, which offers an impressive variety of culinary and retail amusements. After sipping your morning latte or green smoothie creekside at Red Horse Coffee Traders, queue up for a patio table and sausage-stuffed Swedish pancakes at Old Town Cafe, where they don’t skimp on the cinnamon roll icing. After browsing the botanical goods at Beecrowbee and the truffle case at Good Food Award-winning Arrowhead Chocolates, stop into East Fork Brewery for thick, juicy Stangel Ranch bison burgers and pints of Cross-Eyed Cricket IPA.
Slurp post-lunch soft serve at R&R Drive-In, work your way through a whiskey flight at Stein Distillery (call ahead to book a tour), then tour the meticulously curated Wallowa County Museum, where you’ll be urged to partake of the docents’ homemade punch and cookies. For dinner, head ten minutes Swiss-Bavarian architecture has earned the area the nickname “Oregon’s Little Switzerland.” Join the reservations-only crowd at cozy Vali’s Alpine Restaurant, which offers two dinner seatings and one Hungarian-themed entrée nightly, plus homemade doughnuts on weekend mornings—don’t dally, they sell out fast. End the evening back in town with live music on the patio at popular Embers Brew House, which claims the largest selection of microbrews in Eastern Oregon.
Take the long way home through darling Dayville, where the Dayville Cafe serves up hearty slices of homemade country pie at country prices. Across the street, procure provisions or get a flat fixed at Dayville Mercantile, a 122-year-old former school, saloon and dance hall-turned general store and bike shop. In tiny Kimberly, take the rutted road to Thomas Orchards, where the breezy farm store sells just-picked stone fruit and cherries, Triple H Homestead’s raw cow’s milk cheeses, and local honey. In sweet small-town Condon, browse the smallest branch of Powell’s Books and get scoops of Huckleberry Heaven ice cream at Country Flowers gift and coffee shop, then move on to Maupin to ride the Deschutes River rapids with the Imperial River Company before digging in at their resort restaurant.
In Joseph, The Jennings Hotel combines the region’s rich history with modern style—set inside a turn-of-the-century landmark building on Main Street, each of the boutique hotel’s twelve rooms is curated by a different Oregon artist or designer, there’s a cedar sauna just off the main hallway, and the common area combines a full kitchen, wood-burning fireplace, and well-stocked library and record collection. For big views and a dose of nostalgia, book a lake-facing room or cabin at the historic Wallowa Lake Lodge, where guests curl up by the grand stone fireplace in the main lodge on crisp fall evenings. To live that ranch life, check into the homey Wilson Ranches Retreat in Fossil, a 9,000-acre working cattle ranch with a 1910 Sears Roebuck ranch house turned six-room bed and breakfast. After a hearty home-cooked breakfast in the dining room, take a horseback ride through Butte Creek Valley, hike the high desert hills or just read a Louis L’Amour novel in the hammock.