The Ultimate Three-Day Oregon Road Trip

Mount Hood & Route 35 at sunset, Oregon
Anna Gorin / Getty Images

Though Portland may be the first thing that comes to mind when thinking about Oregon, there’s so much more to see simply by heading east and south to the Mt. Hood Territory. This vast area covers 1,870 square miles within Clackamas County, and includes the last leg of the 2,170-mile Oregon Trail, which ended with Barlow Road in Oregon City—some might argue that pilgrimage was the ultimate American road trip back in the 1800s, though thankfully you can experience it today without a large-wheeled wagon and dysentery.

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Willamette Falls, Near Oregon City

Willamette Falls

Mrgadget51 / CC BY-SA

If you're starting in Portland, you'll be shocked to see how quickly the busy city landscape fades away into the calm countryside while making your way 18 miles south on the 205 to the Willamette Falls. This unassuming natural waterfall on the Willamette River—by the way, it's not pronounced Will-a-met, but Will-AM-ette, rhyming with dammit—is the second-largest waterfall in the U.S. by volume.

Pit stop: Even though you've just started your road trip, it's time to switch modes of transportation and join eNRG Kayaking for a 90-minute river kayaking or stand-up paddleboarding adventure. You'll paddle a mile upstream, stopping at the non-operational locks before reaching the base of the falls and then circling back. While the old and defunct paper mills along the way seem entirely out of place among such natural beauty, they're also a nod to the area's industrial past. Watch for osprey perched in their nests atop the power poles, and local tribal members fishing for salmon and harvesting lamprey eels from the rocks.

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Beckham Estate Vineyard in Sherwood

Beckham Estate Vineyard

Courtesy of Beckham Estate Vineyard

No doubt you’re parched from all that paddling, so continue on 205 S toward Wilsonville. At Beckham Estate Vineyard, you’ll be treated to pinot noir fermented and aged in the owner’s handcrafted terra cotta amphora collection. Tastings here are an intimate experience that comes complete with a detailed history of the vintage and, during the summer, incredible views of the property’s towering pine trees, meticulous rows of vines, and deep purple hydrangea planters.

Pit stop: Less than six miles north, Our Table Cooperative offers the farm-to-table experience you’re craving. This regional co-op has an on-farm grocery store carefully curated with largely Oregon-sourced and organic produce and goods. On busy Farm Fridays, from 4 to 8 p.m., order hot food from the kitchen, a local beer or kombucha from their taps, and make some new friends at the communal-style picnic tables on the lawn.

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Kyra’s Bake Shop, in Lake Oswego

Kyra's Bake Shop

Courtney Jade Photography

Begin day two with a 13-mile drive north to Lake Oswego for breakfast at Kyra's Bake Shop. While everything on the menu is delectable, the real reason you're here is the cupcakes: owner Kyra Bussanich is the only four-time Food Network "Cupcake Wars" winner. The most unexpected detail of this scrumptious bakery? Everything, including her award-winning cupcakes, is gluten-free.

Pit stop: Once you're stuffed, you'll make your way toward Mt. Hood. Get your cameras ready, because the Jonsrud Viewpoint—a designated stop on the Oregon Scenic Byways program about 25 miles east of Lake Oswego—is the Insta-worthy photo opp you've been waiting for. On a clear day, it offers spectacular views of snow-topped Mt. Hood and the Sandy River Valley. Hop out of the car, stretch your legs, and peer through the telescope. Once you reach the town of Welches, The Mt. Hood Oregon Resort makes for a fine base camp, complete with a 27-hole golf course and luxury spa.

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Mt. Hood Adventure Park at Skibowl, in Government Camp

Timberline Lodge and Mt Hood.
John Elk / Getty Images

Whether or not you have kids in tow hardly matters once you arrive at Mt. Hood Skibowl. While the winter sports at this adventure park are plentiful, the summer activities don’t exactly suffer: take the scenic sky chairs up the mountain and ride the half-mile alpine slide back down, climb a rock wall, mountain bike, explore the trails on horseback, bungee, kart race or play mini golf or disc golf. You could easily spend the whole afternoon here or just pop by for a few fun activities.

Pit stop: Now it's time to wind your way northeast about 7 miles, up the mountain alpine-lined roads for a closer look at Mt. Hood. It's a towering sight with an always-snowy peak thanks to its 11,250-foot elevation. Even in the summer, you'll find skiers making their way down the south slope, gliding right into the parking lot of Timberline Lodge. Built in 1937 and declared a National Historic Landmark in 1977, the ski lodge stands at an elevation of 6,000 feet—if it looks vaguely familiar, that's because "The Shining" filmed exterior shots of the movie's hotel here. Sadly—or fortunately—you won't find the iconic hedge maze. Stop in to gaze at the massive stone chimney and rugged décor, then enjoy dinner and a cocktail on the top floor at Ram's Head Bar.

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Little Zigzag Falls Trail, in Mt. Hood National Forest

Little Zigzag
Octaviano Merecias Fotografia Photography / Getty Images

For an early-morning walk that will leave you feeling zen all day long, choose the Little Zigzag Falls Trail off Kiwanis Camp Road. There’s only a 100-foot elevation change as you wind through a narrow canyon filled with Douglas fir, western hemlocks, and western red cedar—plus, the ground is carpeted in vibrant greenery. The relaxing sound of the rushing water along the Little Zigzag Creek will lead you half-a-mile to the cascading falls.

Pit stop: If you happen to time your trip just right, there’s one more can’t-miss opportunity to try before heading back toward Portland: alpaca yoga. Yes, the Alpacas at Marquam Hill Ranch gives you the chance to get up close and personal with these curious creatures while doing a downward-facing dog (though they do not climb on you like goats). They’re kept busy grazing during class, but afterward, you’ll be given food to lure them over for a visit.