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Road Trips

How to Plan the Perfect Weekend Road Trip Through Oregon

While unpaved roads and covered wagons are (thankfully) a thing of Oregon Trail past, you’ll still find bucolic wineries, charming stays, and impressive scenery worth the drive. Here’s how to see it all in a weekend.

An avid Italophile, Laura is always on the hunt for the next great travel trends, luxury hotels, best places to eat and drink, and hidden gems. Her writing has appeared in dozens of publications. She also co-wrote "New York: Hidden Bars and Restaurants," an award-winning guide to the city's speakeasy scene.

See recent posts by Laura Itzkowitz

Day 1: Portland

MORNING Start your trip in Portland, one of the Pacific Northwest’s most dynamic destinations known for its enterprising chefs, local artists, surplus of microbreweries and coffee shops, and laid-back sensibility that extends to its best hotels. The Ace is an obvious choice, though the vibe is more college dorm than chic hotel. For something a bit more grown-up but still fun, stay at the Sentinel. The grand lobby retains details from the building’s historic past, while rooms are done up in tweed and evergreen.

AFTERNOON After you check in, head to Pine Street Market for lunch—it’s a collection of stalls by up-and-coming chefs and producers as well as some of Portland’s most beloved restaurants. We loved the green falafel pita at Shalom Y’all and salted caramel soft serve at Salt & Straw’s Whiz Bang Bar. Walk or bike your lunch off along the Willamette River, then head a few blocks west to check out the famous Powell’s Books (JS Tip: A tote bag from Powell’s makes a great souvenir) and quirky boutiques like Tender Loving Empire and Woonwinkel. Or visit the International Rose Test Garden, where you might feel like Alice in Wonderland frolicking around the hedges blooming with brilliantly colored and striped roses. The nearby Japanese Garden is worth a stop if you have time.

EVENING For happy hour, book a table at the Multnomah Whiskey Library, a speakeasy that looks like an old-school library except whiskey bottles line the shelves instead of books. The bartenders serve more than their fair share of Old Fashioneds, but if you ask them for a recommendation (and you should), they’ll geek out over obscure whiskey cocktail recipes. While “farm-to-table” may be a buzzword, Portland chefs take it very seriously, and there are so many standout restaurants here that you really can’t go wrong. One of our favorites is Pok Pok, which truly lives up to the hype with its multi-flavor, Chaing Mai-style dishes and famous chicken wings. If you’re in the mood for a nightcap, head to Pépé Le Moko, the Ace Hotel’s barrel-vaulted underground cocktail lounge for an espresso Martini made with Stumptown coffee.

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Photo by Torsten Kjelistrand, Photo by Lincoln Restaurant

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Photo courtesy of Jamies Francis and Travel Portland

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Photos by Chris Hornbecker

Day 2: The Columbia Gorge and Willamette Valley

MORNING Fuel up in the early hours with Stumptown coffee and a donut. Skip the long lines at Voodoo and head straight to Blue Star Donuts, which makes creative flavors like blueberry bourbon and PB&J. Portlanders love having nature so easily accessible from the city, so do as the locals do and take a detour to see the majestic Columbia Gorge and Multnomah Falls, about 30 minutes east of Portland. A drive along the winding Columbia River Highway takes you passed several other waterfalls, some of which you can hike right up to.

AFTERNOON When you’re ready to vineyard-hop, drive 90 minutes to Carlton, your first stop in the Willamette Valley. Figuring out where to start among the region’s 500 individual wineries can be a bit daunting, but a few stand out from the pack—including Sokol Blosser. Founders Bill Blosser and Susan Sokol Blosser planted their first vines in 1971, and they’re still leaders when it comes to sustainability and organic farming. Stop by to taste their excellent Pinot Noirs and Rieslings in the modern tasting room that looks out over the surrounding valleys. After the wine tasting, you’ll need to fill your stomach. We recommend lunch at The Horse Radish, a casual café that serves great salads and sandwiches on freshly baked bread.

RELATED: 7 Gorgeous Wine Country Hotels Around the World

When you’re ready for another round, head to the Stoller Family Estate in nearby Dundee Hills. Many wineries buy grapes from other vineyards, but not Stoller. In addition to Pinot Noir, they produce Pinot Gris, Chardonnay, Riesling, and Syrah using grapes grown on their 373 acres of vineyards. Fun fact: the airy, modern tasting room runs on solar panels and features reclaimed wood from Powell’s bookstore. If you can, snag one of the Adirondack chairs on the patio for sips with a view.

EVENING Check into the award-winning Allison Inn & Spa, the Willamette Valley’s most luxurious hotel. Of course, this is Oregon, so the property isn’t just beautiful; it’s also LEED Gold-certified. Drop off your bags in one of the 85 spacious rooms and unwind with a walk around the sculpture-dotted gardens or a dip in the pool before dinner at the hotel’s restaurant Jory, where chef Sunny Jin (an alum of the French Laundry and El Bulli) whips up mouthwatering seafood and veggies grown in the property’s garden.

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Photo courtesy of Travel Oregon

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Photo by Carolyn Wells Kramer, Photo by Andrea Johnson

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Stoller Vineyard by Mike Haverkate

Day 3: The Pacific Coast

MORNING If you haven’t fully explored the Allison yet, you’ll want to spend some time there this morning—perhaps to indulge in a treatment at the renowned spa, work out in the fitness studio, or request a tour of the chef’s garden, which is dotted with rows of hazelnut trees (Oregon is the country’s largest producer of hazelnuts).

AFTERNOON Stop for a quick bite at Red Hills Market in Dundee before hitting the road. You’ll drive about two hours northwest through the Tillamook State Forest before reaching Cannon Beach on the Pacific Coast. The beach is known for its giant Haystack Rock and the quaint shingled houses lining the shore. Don’t expect to swim, though: even in summer, it can be cold, so bring a warm jacket.

RELATED: The Dreamiest Beaches to Hit Up in Fall

EVENING There aren’t a lot of hotels in town, but if you want to stay overnight, the Waves is a good option. What the place lacks in style it makes up for in location—right on the oceanfront just minutes from Cannon Beach village with easy beach access. Otherwise, make your way back to Portland on the US26 for one last night in this wild, wonderful state.

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Photos courtesy of The Allison Inn & Spa , Photos courtesy of Travel Oregon

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Photos courtesy of Travel Oregon and Christian Heeb

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Photo courtesy of Travel Oregon

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