Trip Planner: Pendleton

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written by James Sinks | photos by Gwen Shoemaker


For a week every September, Pendleton is the epicenter of the national rodeo universe.

The red paint-splashed Pendleton Round-Up grandstands in this Eastern Oregon city lure thousands for a Western-themed spectacle, launched in 1910, that extends across town and has been described as part John Wayne, part Mardi Gras.

There’s a horse and buggy parade, chuckwagons, country crooners and gallons of disappearing whiskey. At night, crowds pack a neighboring arena for the long-running American Indian pageant, Happy Canyon.

The rush of visitors triples the city’s roughly 16,000 permanent population, cramming every lot with RVs. So many patrons fill the iconic Rainbow Café that it’s said you could have a heart attack and never hit the floor. The rodeo is only one week a year, but the vibe isn’t. Even after the town empties, Pendleton keeps one boot stubbornly planted in its frontier past.

Bronze statues on Main Street and murals celebrate pioneer legends. The city’s motto? “The Real West.” On Court Street, which was laid atop the Oregon Trail, brick facades of shops harbor locally-made wares that will make any cowboy grin: saddles, wide-brimmed hats and beer.

If you’re the unusual sort who isn’t in the market for chaps or boots, Pendleton can still capture your imagination—and a chunk of your bank balance.

Browse art galleries and boutiques, hoist watermelon from the Friday farmers’ market, and sample rich desserts from French-trained artisans at Alexander’s Chocolate Classics. Golf and gambling beckon over the hill at Wildhorse Resort & Casino.

Pendleton was once dubbed the entertainment capital of Eastern Oregon. Long gone are the brothels that contributed to that distinction, but ample G-rated options still await. The city enjoys plenty of sunshine in the shadow of the Blue Mountains, and it’s a short drive through wheat country to uncrowded swimming holes, fishing and kayaking spots, hiking trails and even a mountain bike course carved into a wheat farm and vineyard.

The biggest quandary is which outdoor gear to stuff in the car.

Day 1: Local history | “The Real West” steaks

Long before cowboys came to town and wagons creaked across the Oregon Trail, the Umatilla basin was a home to the Cayuse, Umatilla and Walla Walla tribes.

Immerse yourself in tribal history including the human toll of Western expansion, told in their own words, at the architecturally impressive Tamástslikt Cultural Institute (pronounced Tuh-must-slikt), tucked behind the casino at the Confederated Tribes of the Umatilla Reservation. Also displayed is a wooly mammoth tooth unearthed nearby, which will probably be exciting to dentists.

Just up the road, a former missionary church houses Crow’s Shadow Institute for the Arts, which specializes in imagery using lithographs, a sort of manual printing press. Founded in 1992, the nonprofit workshop and gallery attracts prominent artists to stay and create, and just sold a collection of eighteen prints to the Library of Congress.

Pendleton’s Rainbow Café occupies the oldest brick building and dates to 1883, three years after the city incorporated. The walls display local history in black and white, while one of the clocks tells Dublin time. Irish heritage is celebrated here every St. Patrick’s Day with an ale-fueled parade that wobbles outside and down the block, once an hour.

Aside from the rodeo, the most famous attraction is the original Pendleton Woolen Mill, where clattering looms still stitch spools of sheared wool into patterned blankets. Dig for bargains in the factory store and, four times each weekday, you can join the curious for free thirty-minute tours.

Hoof it through the history of the Round-Up and Happy Canyon at the Hall of Fame, across from the bronze buckaroo at the arena gates. If you’re traveling with a taxidermist, you’ll love War Paint, a (now) stuffed saddle bronc that bucked off 90 percent of its riders.

Check in to your well-appointed room at Oxford Suites and grab complimentary adult beverages and snacks before heading to check out two of Pendleton’s best-known steakhouses.

Cribbage boards wait on the tables at swanky Virgil’s at Cimmyotti’s, where it would be a mistake to miss a pegging opportunity or the blue cheese dip appetizer. The stroganoff is creamy and decadent, the house wine goes down smooth, and the steaks are prime.

Afterward, a half-block away, drink up ambience and strong whiskey drinks at Hamley’s Steakhouse & Saloon, which was opened in 2007 but feels like a century-old Western movie set. On warm weekends, tap your toes to music on the front lawn.

If you have children in tow, or not, you’ll want to stay abreast of the artwork. The restroom paintings drift into the risqué.

Day 2: Sordid Tours | Handcrafted leather goods | Gamblin’

A levee built to keep the Umatilla River from spilling into downtown can also help keep your cholesterol in check. The rocky berm sports a three-mile asphalt path, perfect for a riverside workout with a babbling soundtrack.

Two blocks away, follow your nose to the city’s only coffee roaster. Buckin’ Bean Coffee percolates in a neighborhood of historic homes including the Italianate Pendleton House, which is now a B&B.

The once-bawdy red light district is the centerpiece of a kitschy walking tour, which offers a look inside an abandoned brothel. Pendleton Underground Tours ($15) zigzags under a city block through basement tunnels and a holding cell purportedly used by Chinese emigrant workers.

If you have kids and would rather not explain the point of a bordello, the Children’s Museum of Eastern Oregon is just around the corner.

Treat your taste buds and your ears at The Great Pacific Wine & Coffee Co., which offers a wide cheese selection, pizzas, sandwiches, beers and wine by the bottle—as well as a foot-tapping local bluegrass jam session on Saturday afternoons.

While downtown, saunter among store- fronts and meet handcrafters who hew leather and felt into Western garb; and it ain’t a computerized assembly line. A single custom hat from Montana Peak Hat Co., whose clientele includes movie stars, can take twelve hours of labor to complete.

At the Hamley & Co. Western store, the saddle shop dates back to 1883 and has churned out an estimated 33,000 of them since. Depending on the intricacy, saddles can take upwards of three weeks to complete and base models start at $3,800.

Pendleton’s rodeo identity is more than niche marketing. Backyard arenas dot the landscape and at the Mustangers rodeo club, you can order up biscuits and gravy and watch amateur ropers kick up dust. Downtown, retired competitors set up shop.

A decade ago, Richard Stapleman, a wiry 51-year-old with a horseshoe mustache and a big belt buckle, measured success in eight- second chunks as a professional bull rider. Now, he’ll spend a week on a single pair of ornate cowboy boots in his storefront, which he shares with another former buckaroo.

For the clique of local handcrafters, Black Friday arrives in September. “Just about the time you think you’re caught up, the Round-Up comes to town,” he grinned.

Don’t let the name fool you into going else- where for dinner at Pendleton Coffee Bean & Bistro. The dinner menu is a far-beyond-java marriage of cattle country and Baja flair, including a crusted ribeye, prawn salad, ceviche and a decadent pot de crème.

If you’re over 21 and like to hit 21, catch the free hourly shuttle to the casino for some nightlife. Or head to Crabby’s Underground Saloon, where the pool tables are open early, and the locals roll in late.

Day 3: Winning drinks | Wildhorse golf | Umatilla County adventures

Every year, the watering holes in Pendleton vie for the best drink in a “battle of the bars,” held in the Let ’Er Buck Tavern beneath the Round-Up grandstands.

Taste the reigning champion—a huckle- berry-infused “buckaroo”—at Sundown Grill and Bar-B-Q, operated by a husband and wife team with gourmet cooking and American Indian roots. If the setting in a 1904 historic house doesn’t impress you sufficiently, the mushrooms or rattlesnake sausage will. Plus, there’s lobster frittata on the brunch menu.

Outdoor recreation options in Umatilla County read like a multiple choice test without a wrong answer.

Swing for birdies at the wide-open golf links at the Wildhorse Resort, or throw a line for fish at McKay Reservoir, six miles south of town. On warm days launch yourself off rope swings into the Umatilla near Bar M Ranch. There’s a frisbee golf course at Community Park, and you can rent discs at the office.

If you brought bikes, the lightly traveled roads through wheat country and into the foothills offer short and long options. Pendleton has been a repeat camping point for the annual late-summer Cycle Oregon caravan.

If rough terrain is your fancy, take a short drive to the farming community of Echo. The owners of Sno Road Winery, who travel the globe to judge skiing events when they’re not crushing grapes and serving wine, have devel- oped a public network of mountain bike trails on their property, just outside town.

Their place hosts the state’s first mountain bike race each spring, known as Red-to-Red.

The Sno Road tasting room sits at the end of Main Street, just steps away from Oregon Trail exhibits at a tiny riverside park. The tempranillo is velvety.

Back in Pendleton, a former car dealership houses the city’s first craft brewery and a “beer named Sue.” The Prodigal Son Brewery and Pub touts pub fare such as burgers and temptation from the fryer, plus calamari tacos, house-made bratwurst and a tart that mingles Pendleton Whiskey, hazelnuts and chocolate.

The place earned its name because it was founded and is run by Eastern Oregon classmates, including a former Rogue Ales brewmaster, who left and came back home.

From tables in front under the neon sign, you can gaze westward down Court Street, into the brick-filled heart of Pendleton. Beverage in hand, it’s a fitting spot to plot your own return.

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