From the Columbia River Gorge to Oregon’s High Desert: Where to Play, Eat, and Stay East of Portland

Things to do east of Portland Columbia River and Hood River Valley Columbia River Gorge Photo: Richard Philion The Columbia River Gorge has one of the largest concentrations of waterfalls in North America. Many line the winding Historic Columbia River Highway, known as the “King of Roads.” Some require a hike, while others, such as Shepherd’s Dell, sit just off the highway. Multnomah Falls, Oregon’s tallest waterfall, is perhaps the highway’s most recognizable. It drops 620 feet in two tiers, and the 1914 Benson Bridge crosses between them. Hood River Fruit Loop Photo: Richard Philion More than 2,500 apple varieties are cultivated in the United States, and Kiyokawa Family Orchards in the Hood River Valley grows more than 120 of them. The Kiyokawa family has farmed the valley since 1911 and works to preserve rare and heirloom varieties. Browsing the wooden bins at the orchard’s store, or picking your own directly from the orchard, gives you the chance to discover less-common varieties that don’t keep long enough for grocery stores. Kiyokawa is one of about 30 stops on the Hood River Fruit Loop, a 35-mile drive past orchards, farms, and wineries. Along the loop, you can sip crisp pinot gris at one stop and bite into a pink-fleshed Mountain Rose apple or Anjou pear at another (Hood River County is the world’s leading producer of Anjous). I quickly learned to pace myself while sampling. Kiyokawa Family Orchards: 5625 Hutson Dr, Mt Hood, OR 97041 Mount Hood Railroad Photo: Richard Philion For views of the Hood River Valley, ride the Mount Hood Railroad, which departs from downtown Hood River. The line opened in 1906 to haul lumber from a mill at Dee and later carried the valley’s fruit to market. About three miles out of town, the train reverses direction on a switchback to climb the grade, one of only five railroad switchbacks still in use in the US. Today, the train carries passengers up the valley to The Fruit Company, where you can taste wine, tour a fruit-packing museum, or wander among rows of grapevines and fruit trees beneath Mount Hood. If you visit in the fall as I did, you’ll ride past the valley’s changing foliage. Mount Hood Railroad: 110 Railroad Street, Hood River, OR 97031 Pendleton Pendleton Round-Up Pendleton captures the spirit of the West. Every September, during the second full week, the town’s population swells from about 17,000 to more than 50,000 for the Pendleton Round-Up, one of the most prestigious rodeos in North America. The rodeo’s rallying cry is “Let ’er Buck!” Since the first Round-Up in 1910, local tribes including the Cayuse, Umatilla, and Walla Walla have set up a tepee village next to the stadium and taken part in the rodeo and its festivities. Interwoven, a new fashion and culture festival celebrating Indigenous and Western makers, debuted in October 2026. It featured multiple runway shows, including one on horseback, along with artisan markets and a fashion-inspired brunch pairing local chefs with designers. Pendleton Round-Up: 1205 SW Court Ave, Pendleton, OR 97801 Interwoven: 601 Westgate, Pendleton, OR 97801 Downtown Pendleton Photo: Richard Philion You don’t have to visit during one of Pendleton’s festivals to experience its culture. A walk through historic downtown shows that this is a city of makers. Cowboy boots, belts, saddles, and much more are made here. Stop by Stapleman Custom Boot Shop, where Richard Stapleman, a former bull rider, still builds boots largely by hand (although you’ll face a yearlong wait for a custom pair). Take some time to explore Hamley & Co., the sprawling Western store that started as a saddle shop. I made my way to the back, where you can still watch saddle makers at work. End the day at the Rainbow Cafe, which claims to be Oregon’s oldest continuously operating bar, dating to 1883 (the claim is disputed by the Pioneer Saloon in Paisley, Oregon). Cowboy hats are common but not required. Stapleman Custom Boot Shop: 7 SE Court Ave, Pendleton, OR 97801 Hamley & Co.: 30 SE Court Ave, Pendleton, OR 97801 Rainbow Cafe: 209 S Main St, Pendleton, OR 97801 Pendleton Underground Tours Descend a set of stairs you probably didn’t notice from the sidewalk, and you’ll explore historic basements and sidewalk vaults with a guide from Pendleton Underground Tours. Guides recount stories of speakeasies, Chinese laborers’ living quarters, and opium dens (though historians writing for the Oregon Encyclopedia have challenged parts of the tour’s account of the city’s Chinese community, including the idea that Chinese immigrants built the tunnels). After about an hour underground, watching the feet of passersby through a few surviving purple-hued prism-glass panels, known as vault lights, you’ll head upstairs to Madam Stella Darby’s Cozy Rooms. Darby, the city’s most famous madam, ran a brothel here from 1928 to 1967. Guides tell stories of buttons dropped from above to entice customers, police raids, and the priest who delivered a sermon every Sunday in the bordello’s private parlor. They also credit Darby as a generous supporter of the community. Pendleton Underground Tours: 31 SW Emigrant Ave, Pendleton, OR 97801 High Desert Crane Hot Springs Photo: Richard Philion Crane Hot Springs sits in the state’s expansive high desert, about 20 miles outside Burns. Eastern Oregon is also one of the country’s top locations for dark-sky viewing, with many areas in the region achieving Bortle Class 1 — the darkest classification for night skies. With little to no light pollution, the Milky Way is easily visible on clear evenings while you’re soaking in the mineral-rich waters. The area is also a stopover point for migratory birds. Nearby Malheur National Wildlife Refuge is worth visiting during the spring and fall migratory months. Crane Hot Springs also has trails encircling the ponds that make birdwatching easy. Crane Hot Springs: 59315 OR-78, Burns, OR 97720 Malheur National Wildlife Refuge: 36391 Sodhouse Ln, Princeton, OR 97721 Where to eat and drink east of Portland Brigham Fish Market Overlooking the Columbia River in Cascade Locks, Brigham Fish Market is run by sisters Kim Brigham-Campbell and Terrie Brigham, members of the Confederated Tribes of the Umatilla Indian Reservation. Their family has fished the river for generations, and the market sells whatever the river provides: coho, sockeye, chinook (the most popular, according to Terrie), and steelhead. Take smoked fish to go, or grab a seat on the outdoor patio for a smoked salmon po’boy and a huckleberry lemonade. Brigham Fish Market: 681 Wa Na Pa St, Cascade Locks, OR 97014 Alia Alia, the restaurant at the Lightwell Hotel in Hood River, opened in fall 2026 and pairs Mediterranean dishes with Northwest ingredients. Chef Anthony Dao’s menu features dishes like charred octopus skewers, malfouf mahshi (stuffed cabbage rolls), and Northwest salmon, all complemented by local Hood River wines. Save room for the baklava. Alia: 201 Cascade Ave, Hood River, OR 97031 Grateful Vineyard For lunch with a volcano view, visit Grateful Vineyard, where rows of grapes draw your eyes to Mount Hood (an active stratovolcano that’s currently dormant) in the distance. Its salads and fig, pear, and arugula pizza highlight the region’s produce. Pair either with one of the wines, ciders, or beers made on site. Grateful Vineyard: 6670 Trout Creek Ridge Rd, Mt Hood, OR 97041 Hamley Steakhouse & Saloon After a day of “letting ’er buck,” head to Hamley Steakhouse & Saloon for dinner. Next to Hamley & Co.’s Western store, the restaurant serves USDA Prime beef (and lots of other non-beef options) in the building Hamley’s has occupied since 1905. The steakhouse opened there in 2007, and the Confederated Tribes of the Umatilla Indian Reservation have owned the business since 2019. Its 100-year-old mahogany bar, stained glass, and Western memorabilia evoke the Old West. Order a Midnight Manhattan, made with Pendleton Whisky. Hamley Steakhouse & Saloon: 8 SE Court Ave, Pendleton, OR 97801 Oregon Grain Growers Brand Distillery If you’re looking for pizza (Detroit-style, Chicago-style, or Neapolitan), look no further than the Oregon Grain Growers Brand Distillery. Located in a former Cadillac and Oldsmobile dealership, the distillery serves arguably the best pizza in Pendleton and some of its most interesting cocktails. I couldn’t say no to trying the pickle-brine vodka in a Curious Martini with coconut and lime. Oregon Grain Growers Brand Distillery: 511 SE Court Ave, Pendleton, OR 97801 CORAZÓN Artisan Kitchen CORAZÓN Artisan Kitchen (open Friday through Sunday and located on the Crane Hot Springs property) is conveniently located if you want a bite to eat without having to step out of your bathrobe. Janne Valdez serves small-batch, handmade tortillas; house-made chorizo; chicken tinga; al pastor; tamales; fresh salsas; and seasonal specialties. Be sure to ask her if she has any cheesecake available; I’m already planning a trip back to get some more. CORAZÓN Artisan Kitchen: 59315 OR-78, Burns, OR 97720 Where to stay east of Portland Lightwell Hotel & Spa Photo: Richard Philion The Lightwell Hotel is a convenient base for exploring the Hood River Valley. Located in downtown Hood River, it’s steps away from the Mount Hood Railroad and Oak Street, lined with artisan shops and boutiques. The rooms have been recently updated. The hotel features a rooftop patio with Columbia River views, and the lobby has a baby grand piano and comfortable sofas for relaxing. End a busy day of chasing waterfalls and sampling wine by visiting the subterranean spa with a sauna and a hot soaking tub. Lightwell Hotel & Spa: 201 Cascade Ave, Hood River, OR 97031 The Hotel Pendleton The Hotel Pendleton, a 1962 motel renovated in 2023, puts you within walking distance of the city’s makers and shops. Hamley & Co. sits across the street, and Stapleman Custom Boot Shop is half a block away. The Hotel Pendleton: 105 SE Court Ave, Pendleton, OR 97801 The Pendleton House Historic Inn Bed & Breakfast For a more intimate stay, the six-room Pendleton House Historic Inn Bed & Breakfast sits just across the Umatilla River. Affectionately known as the “pink house,” the 1917 Italian Renaissance-style mansion is one of the colorful historic homes in the neighborhood. The Pendleton House Historic Inn Bed & Breakfast: 311 N Main St, Pendleton, OR 97801 Working Girls Hotel If you’re really taken with the Pendleton Underground tour, stay at the Working Girls Hotel, where Pendleton Underground Tours converted part of the former bordello into a suite and four guest rooms in 1991. The rooms are furnished in Victorian decor, with 18-foot ceilings. Working Girls Hotel: 17 SW Emigrant Ave, Pendleton, OR 97801 The Retreat at Silvies Valley Ranch Photo: Richard Philion Don’t let the private airstrip deter you. For all its luxury, The Retreat at Silvies Valley Ranch is down-to-earth and casual, and the property is still a working cattle ranch, spread across 150,000 acres. On McVeigh’s Gauntlet, a seven-hole course, you can have a goat as a caddie (yes, they really do have goats that carry your golf clubs). There’s also a spa, and the night skies are free of light pollution. The Retreat at Silvies Valley Ranch: 10000 Rendezvous Lane, Seneca, OR 97873 Crane Hot Springs Photo: Richard Philion At Crane Hot Springs, you can sleep steps away from the hot spring pool. The property has a number of accommodation types, including traditional tepees, cabins, suites, and camping pads. The suites and tepees each have a private soaking tub that can be filled with mineral spring water. The springs are open for overnight guests 24 hours a day. I practically lived in my swimsuit and the plush bathrobe provided by the property, enjoying multiple soaks. Crane Hot Springs: 59315 OR-78, Burns, OR 97720 Getting to and around inland Oregon This trip covers a lot of ground. Oregon is the ninth-largest state in the country, and Portland International Airport (PDX) is the most practical gateway. A rental car is essential for the long distances between stops, but you’ll be rewarded along the way. The Historic Columbia River Highway was the first scenic highway in the US designated a National Historic Landmark. As you head east, rainfall drops and the forests give way to sagebrush. Our route between Pendleton and Crane Hot Springs passed through the Umatilla and Malheur National Forests and across wide, sweeping plains. Getting around requires a vehicle, as most locations are separated by large distances. However, the cities of Hood River and Pendleton are both very walkable and best explored on foot. First Nature Tours also provides custom itineraries and guided tours in the region. More like this