A snowcapped volcano, a river rushing through a dramatic gorge and an authentic Wild West town — they all make for an adventurous trip from Portland, which is one of the leading design and food cities in the United States and the perfect jumping off point to explore Oregon’s untamed landscapes.

Drive along the mighty Columbia River to reach the charming town of Hood River, which abounds with wineries, fruit farms and sophisticated restaurants. From there you can detour an hour’s drive south to explore the state’s highest peak, Mt. Hood, a year-round recreation mecca with an iconic hotel, Timberline Lodge, on its northern slopes.

You can then follow I-84 farther alongside the Columbia River and through the rugged and sparsely populated Wallowa Mountains to tour Eastern Oregon, home to the Wild West cowboy culture of Pendleton and a jumping-off point for jet-boat tours through awe-inspiring Hells Canyon.

Day One: Portland

One of the city’s newer and certainly most noteworthy shopping experiences, Union Way is a strikingly designed, covered arcade of diminutive boutiques, many of them based in Oregon. Set in the heart of the trendy West End and steps from the chic Pearl District and iconic Powell’s City of Books, this intimate passageway with blond-wood walls and skylights is home to Portland-based boot shop Danner, jewel-box candy maker Quin (try the blackberry-and-tangerine gumdrops), modern personal-care and grooming shop Spruce Apothecary, dapper men’s and women’s clothier Steven Alan, and several others.

Across the river, near the city’s bustling Mississippi/Williams retail and dining corridor, Beam & Anchor captures Portland’s rustic-contemporary aesthetic with its beautifully curated selection of household goods, from white ceramic beer growlers to vibrantly colored antique Navajo rugs.

Make plans for dinner at Coopers Hall, an airy converted industrial space containing one of the city’s acclaimed urban wineries, as well as a taproom pouring local wines, beers, ciders and creative cocktails, and a kitchen that turns out delicious platters of small-plate dishes, such as fried-duck confit and artisan cheeseboards.

(Portland photo credit: Satoshi Eto)

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Day Two: Columbia River Gorge and Mt. Hood

Less than a 20-minute drive east of Portland along I-84, you’ll first encounter the jaw-dropping beauty of the Columbia River Gorge, a glacially carved, 70-mile canyon that forms the border between the states of Oregon and Washington. Spend the morning visiting the corridor’s signature attractions, including the Vista House, a 1917 octagonal structure set on a 725-foot-tall rampart that affords mesmerizing panoramas for many miles up and down the river. Nearby is an area known as a “waterfall alley” featuring several impressive cascades situated along the narrow, two-lane Historic Columbia River Highway Scenic Byway. This area is popular for a reason, so avoid the crowds by visiting early on a weekday and carpooling. Don’t forget to check out the mammoth Bonneville Lock and Dam, where a visitor center contains exhibits on this 1938 hydroelectric plant, as well as an underwater window where you can view salmon working their way valiantly up a fish ladder to their native spawning grounds.

It’s a 30-minute drive to Hood River, where you’ll find plenty of excellent dining options in the walkable downtown, including one of several acclaimed brewpubs, Double Mountain Brewery & Taproom. Drop in for a hearty lunch of brick-oven-baked thin-crust pizza or a house-made Kölsch beer sausage, and sip a pint or two of the exceptional beers — perhaps the ruby-hued and richly robust India Red Ale or the authentically Dublin-style Black Irish stout. Next hop onto Highway 35, the scenic road leading to Mt. Hood, to reach Draper Girls Country Farm, one of the most famous fruit growers in this region, known for apples, peaches, pears and all sorts of berries. You can pick your own fruit and purchase fresh ciders, jams and honeys.

Highway 35 continues another 30 miles south to snowcapped Mt. Hood, which, at 11,250 feet is the highest point in Oregon and a beacon visible from miles away (you can see the peak easily from downtown Portland on clear days). Home to three different ski areas, Mt. Hood and the surrounding national forest also offer endless trails for hiking as well as campgrounds, fishing lakes and even a renowned golf course operated by the nearby Resort at the Mountain. Cap off your explorations by visiting rustic yet stately 1930s Timberline Lodge, which hugs the northern slope of Mt. Hood at an elevation of nearly 6,000 feet. Even on warm days, pack a jacket — the temperature at the lodge is typically 15 to 20 degrees colder than in nearby Hood River. With its massive stone fireplace and giant wood beams, the lodge’s Cascade Dining Room and adjacent Ram’s Head Bar are favorite spots for drinks or dinner. Enormous windows provide spectacular views, especially at sunset.

Head back on Highway 35 and spend the night in Hood River, which has a mix of distinctive hotels and upscale bed-and-breakfasts.

(Columbia River Gorge and Vista House photo credit: Larry Geddis)

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Day Three: Hood River to Pendleton

Start your morning in Hood River by visiting one of the more unusual attractions in the state, the Western Antique Aeroplane & Automobile Museum, which contains a collection of more than 250 still-operational vintage planes, cars and motorcycles, including a 1910 Parker-Curtiss Pusher biplane, a 1941 Lincoln Zephyr sedan and a 1927 Harley-Davidson JD motorcycle.

Drive east along I-84, which fringes the Columbia River for the next 100 miles, to the SAGE Center in the small town of Boardman. This contemporary visitor center contains interactive exhibits devoted to the region’s continued efforts toward renewable energy and sustainable agriculture. You can ride a simulated hot-air balloon, see how GPS and other advanced technology is shaping local farming production, and purchase local jewelry, art, and gourmet goods and wine in the Sage Center store.

Next venture a bit inland from the Columbia Gorge to the ranching and farming center of Pendleton, which is famed for the colorful blankets and textiles produced by its Pendleton Woolen Mills, as well as for hosting one of the nation’s largest and most beloved rodeos each September, the Pendleton Round-Up. Also in Pendleton and taking place the same week as the Round-Up, the Happy Canyon Indian Pageant and Wild West Show — a tradition since 1916 — delights spectators with its rollicking theatrical presentation of Eastern Oregon’s rich and colorful pioneer and Native American heritage.

No trip to Pendleton is complete without stopping to browse the colorful and ornate hand-tooled leather boots, classic cowboy hats, and other fine art and accessories at Hamley & Co. Western store and custom saddlery, a fixture in downtown since 1905. As the sun sets over picturesque Pendleton, enjoy a leisurely cowboy-style steak dinner. Virgil’s at Cimmiyotti’s has been a favorite choice of discerning carnivores for more than 60 years. In the darkly lighted, atmospheric dining room, feast on the restaurant’s signature dish: filet mignon topped with bacon and glazed with a Pendleton Whisky reduction.

Spend the night in Pendleton.

(Photo of Pendleton Round-Up)

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Day Four: Hells Canyon and Baker City

Get an early start from Pendleton and make the 3.5-hour drive via I-84 to tiny Oxbow, where you can set off on a rousing jet-boat tour with Hells Canyon Adventures, which offers a variety of excursions along the famed Snake River. A good option for beginners, the two-hour Wild Sheep tour has two daily departures and explores one of the deepest sections of the gorge. Guides explain the rich local history and geology, as well as point out wildlife from sheep to bears, which sometimes appear along the cliffs fringing the river.

Backtrack two hours by car to Baker City, the largest community in vast Eastern Oregon, but still a place with a friendly and relaxing small-town feel. Along the wide Main Street, one of the prettiest in the state, you can browse a colorful selection of independently owned shops carrying everything from locally made arts and crafts to artisan chocolates and microbrew beers. Learn about pioneers and settlers at the 500-acre National Historic Oregon Trail Interpretive Center, which includes parts of a historic gold mine and wagon ruts carved during the famous journey.

Spend the night at the opulently restored Geiser Grand Hotel, a handsome 1889 boutique hotel that retains such original architectural elements as ornate crystal chandeliers, carved and polished mahogany woodwork, and a dramatic stained-glass ceiling above the elegant dining room, a favorite destination for dinner.

(National Historic Oregon Trail Interpretative Center photo credit: Sumio Koizumi)

Pendleton Oregon

Day Five: Back West

Return via I-84 to Portland, which is about a five-hour drive from Baker City.

(Road near Pendleton photo credit: Joni Kabana)

If you liked this, you may be interested in our other Oregon Food Trips. Go see them here!

Learn about all of Oregon’s Food Trips

These maps and directions are for planning purposes only. You may find that construction projects, traffic, or other events may cause road conditions to differ from the map results. For travel options, weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941.

About the Author: Andrew Collins

Andrew Collins lives in Portland and writes about Oregon for a variety of outlets, from Fodor's Travel Guides to About.com. He's the editor of The Pearl Magazine and teaches food- and travel-writing classes for Gotham Writers' Workshop. Andrew spends his free time road-tripping, hiking, winery- and brewery-hopping around the state with his partner (and fellow travel scribe), Fernando Nocedal.

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