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Home Road Trip Where to Eat, Stay, and Play on an Eastern Oregon Road Trip

Where to Eat, Stay, and Play on an Eastern Oregon Road Trip

by Staff

The drive out east can be a slog, but there’s plenty to feast your eyes and mind on if you know where to go. Plus, it’s much more entertaining if you make a road trip out of it and break the drive into more manageable chunks. Here’s where to stop.


3.25 hours east of Portland

Claim to Fame: Its biggest event, the Pendleton Round-Up rodeo, celebrates its 113th year in September, and Pendleton Woolen Mills, the maker of fine blankets and clothing, still has a major outlet on the site of the old mill (though its headquarters is in Portland). While the cowboy spirit of the West is alive and well here, so is the rich Native American heritage of the local Umatilla, Cayuse, and Walla Walla peoples who make up the nearby Confederated Tribes of the Umatilla Indian Reservation

Stop for: The 45,000-square-foot Tamastslikt Cultural Institute, which presents the impact white settlers had on the area, how the tribes’ economy continues to develop today, and what the future holds for its people. 

Where to Sleep: The nearby Wildhorse Resort & Casino is as near to Vegas-style accommodations as you can get in Oregon, but with a heck of a lot more charm. The resort offers entertainment and food for kids and adults, including a championship golf course, bowling alley, arcade, and movie theater in addition to a large gaming floor. 

La Grande

1 hour southeast of Pendleton

Claim to Fame: Home to Eastern Oregon University (2,700 students), this college town was settled in the Oregon Trail era and prospered with mining and agricultural processing, which funded a few stunning art deco buildings on its main drag downtown, including the Liberty Theater. 

Stop for: A meal and some shopping. Within a few blocks, visitors can snag sassy dishtowels and kitchen essentials at Bella Mercantile; candles, cute bags, and that gnome you’ve always wanted at Rosewood Cottage; camping gear at Blue Mountain Outfitters (admire the antique lanterns hanging in the store, too); and a vintage apron and sparkly duds from the “Bling” section at Royal Clothiers consignment shop. For eats, options include classic drive-thru Nell’s-N-Out for steak burgers, curly fries, and milkshakes; schmancy pastries and baguette sandwiches at Liberty Theatre Café; and elevated pub grub at Side A Brewing, which occupies an old firehouse a block over and serves pints of There B Flowers single-hop pale ale and Censorship Is Lame coffee stout. 

Where to Sleep: La Grande is well stocked with modern chain hotels, but for a real time warp, travelers can head a few minutes east to the Lodge at Hot Lake Springs and check out the ongoing restoration of an old sanatorium perched over a natural steaming geothermal pond sided with soaking tubs. The pair of yurts at the Grande Hot Springs RV Resort next door is a favorite among locals. 

Enterprise & Joseph

1.5 hours east of La Grande

Claim to Fame: These neighboring towns sit on the edge of the Wallowa Mountains, en route to Hells Canyon, the deepest river gorge in the US.

Stop for: In Joseph, take a tour of Valley Bronze, a foundry whose statues and monuments dot points around the world, and then continue the theme of heat and melty dark materials at Arrowhead Chocolates. If you need a real meal, The Blythe Cricket has baked oatmeal, “jacked-up” corn cakes packed with black beans and poblano peppers for breakfast, and a solid soup-salad-sandwich lunch menu. For dinner, the 26-year-old Terminal Gravity Brewing in Enterprise

beckons with a busy events calendar and heaping nacho plates, hippie-pleasing seasonal salads, burgers, mac and cheese, and a yam-studded veggie curry alongside its house IPAs and pilsners. Sit in the cozy taproom, claim a picnic table on the lawn while the kids play in the creek, or, when the weather turns cold, enjoy a pandemic development that’s sticking around: walled tents with private tables, strung with fairy lights and visited by the resident cat. Locals are still mourning Joseph’s Gold Room, the restaurant started in 2019 by Ava Gene’s alums who closed shop when they were lured back to Portland last winter as Ava Gene’s reopened. 

Where to Sleep: Just upstairs from the shuttered Gold Room is the Jennings Hotel—once a buzzy, Kickstarter-funded “next big thing”—which has mellowed into a charming set of art-themed second-story rooms, with a shared sauna and library/kitchen/lounge. At the south end of Wallowa Lake, find a hopping family vacation scene, with the century-old Wallowa Lake Lodge open May through September. The lodge’s charming cabins, just a stone’s throw away, can be rented year-round, and the lodge itself hosts conferences, reunions, and more during the off-season. 

Baker City

45 minutes south of La Grande

Claim to Fame: Once the largest settlement between Salt Lake City and Portland, Baker City today promotes itself as a base camp for the region, with its proximity to the winter ski routes and summer hiking trails of Anthony Lakes, Hells Canyon and the rest of the Snake River, and heritage sites like the National Historical Oregon Trail Interpretive Center and the Sumpter Valley Railroad

Stop for: Downtown’s not nearly as bustling as it was around 1900, but it’s a great place to grab a book, a beer, and a bite. Now in its fifth decade, Betty’s Books readily provides reads. At Barley Brown’s Brew Pub, travelers and locals fill up on the 25-year-old brewery’s award-winning pints. Started by an alum of the short-lived WNBA team Portland Fire, Sweet Wife Baking draws a morning crowd for coffee and pastries to go, plus Bloody Marys and hearty plates like the Ziggy Piggy, a biscuit topped with sausage gravy, bacon, and a fried egg. 


2.75 hours southwest of Baker City

Claim to Fame: This seat of Oregon’s largest and least densely populated county is a great home base for exploring some of the state’s most secluded high desert secrets, from the rugged playground that is the Alvord Desert, in the shadow of Steens Mountain, to the Malheur National Wildlife Refuge, where visitors can revel in viewing more than 300 species of birds and scores of mammals. 

Stop for: Spend a quiet moment in Bella Java reading a book with a slice of quiche and an espresso before making the 25-minute drive southeast to Crane Hot Springs for a soak in a private tub large enough for friends to share, or dip into the outdoor pool and enjoy the view. It’s the perfect way to relax before heading south for a hike in the Steens area (if weather permits), where you might catch a glimpse of wild Kiger mustangs. 

Where to Sleep: The Historic Central Hotel (read more below) sets the tone for your stay in Harney County with its Prohibition-era western vibes packaged in a boutique hotel—the execution of which is spot-on and unobtrusive.

An Historic Hotel Gets a New Life 

Jen and Forrest Keady bring a slice of the 1920s to hotel guests in 2023.

If you ignore our earlier advice and muscle through the six-hour drive from Portland, you may arrive in Burns for your stay at the Historic Central Hotel after-hours. Not to fret: this handsome and cozy hotel might have “historic” in its name, but the logistics of checking yourself in could not be more modern with its door code keys—emailed to you ahead of time—that double for building and room access. That feature is a pleasant surprise from a hotel built in 1929, where you feel that you’ve stepped back in time as you traverse the creaking stairs up to your room. Twelve beautifully refurbished rooms bearing names like Whippersnapper, Swanky Diggs, and Flapper Girl are clean and comfortable. Each is adorned with a note from hotel management espousing positive fortune cookie fodder, and around each corner you’ll find laser-cut metal signage with pithy sayings about slowing down to enjoy the moment. Note that five rooms have only sinks, meaning that you share a bathroom with fellow guests, with the water closets at either end of a short hallway and renovated to today’s standards with old-fashioned charm. (We shared, and it wasn’t an inconvenience.) 

The building sat idle for 20 years before being purchased in 2016 by Burns couple Jen and Forrest Keady, who breathed new life into its old bones. They also renovated the town’s nearby masonic lodge and recently purchased a main street building for a new project.

Make sure to take advantage of the hotel’s back patio area—a large space behind the hotel with its own bar, firepits, corn hole, plenty of seating, and an upper deck area to take in the expansive view to the east. The scene attracts an interesting crowd, where you might meet rafters en route to the John Day River, or bird-watchers heading to the Malheur National Wildlife Refuge. Introverts can head to a wood- and stone-laden lounge area dubbed the Living Room, which sits inside the bottom floor of the hotel and provides a homey space to chat over drinks, play a board game, or just relax. Below that sits the hotel’s “speakeasy”—a repurposed boiler room containing the hotel’s original boiler and coal shoot—which can be reserved for private wine and whiskey tastings, Prohibition-era roots be damned. —SS

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