Perfect Winter Road Trips for When You Need to Escape Portland

From cozy towns to skiing adventures, there are plenty of good reasons to take a quick break from Portland.

Bend, Oregon
Sparks Lake in Bend, Oregon | tusharkoley/Shutterstock
Sparks Lake in Bend, Oregon | tusharkoley/Shutterstock

We get it: as great as Portland is—with its bars and restaurants, date spots, and nightlife—sometimes you need to leave town for a bit, even if it’s only for a day or a weekend. This can be especially true in winter, when the city is under an oppressive pall of gray skies and drizzly rain, and you need an escape to someplace snowy or at least less damp. Luckily, there are plenty of areas within driving distance to make a hasty retreat, and we’re not just talking about the overtrodden landmarks like Cannon Beach or Timberline Lodge. Keep in mind that traveling Oregon highways in winter can lead to unpleasant, or even dangerous, conditions, especially with the still-raging pandemic. Be sure to check weather advisories before hitting the road, and to take COVID-19 precautions seriously.

Distance from Portland: One hour
Heading to wine country is often considered more of a summertime jaunt, but there’s something charming about visiting this small town in winter time, especially if snow has recently fallen. More than a launching point for the hundreds of surrounding vineyards and wineries McMinnville offers numerous dining opportunities like the Americana-tinged Community Plate and the Neapolitan pizzeria Pizza Capo. Of course, it is situated directly in wine country, which means it’s an easy jaunt to some of the state’s best wineries, with a unique, wintery view of the snow-dappled vineyards.
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Hood River, Oregon
Hood River, Oregon | tusharkoley/Shutterstock

Distance from Portland: One hour, five minutes
Sure, Hood River is an obvious day trip destination from Portland, but normally people are visiting for windsurfing and other summer pastimes, so beat the crowds of tourists and head here in winter. The beer from breweries like pFriem and Double Mountain taste as good in February as they do in August, and a multitude of trailheads are just miles from the town. It’s an easy place to spend a long weekend away from the noise of the city, while still having the comfort and amenities of a town.
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Distance from Portland: Two hours
Eugene is most famous for being home to the University of Oregon and the tens of thousands of students that attend, but it’s more than just a place to catch a Ducks game. Winter time provides a chance to go truffle hunting in the numerous woods that surround the town, after which you can grab some of Oregon’s best ciders from WildCraft, which sources all of its fruit locally. Those looking for an elegant night out can visit the famed Marché restaurant or grab a cocktail and sushi from Akira. Sy’s Pizza is a legitimate New York-style pizzeria, and the Bier Stein rivals any tap house in Portland. Just be sure to avoid Rennie’s Landing, Max’s, or the Webfoot unless you really want to rub shoulders with college students. Those looking for more outdoorsy activities will find that the hills and paths around town are frequently used by runners.
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Government Camp, Oregon
Government Camp, Oregon | CSNafzger/Shutterstock

Distance from Portland: One hour, 15 minutes
On the snowy banks of Mt Hood, Government Camp is an endearing alpine village that serves as a launching point for many Mt Hood trips. Obviously, skiing and snowboarding are the main draws here, but there are also ample winter trails to hike, snowshoeing areas, and even horse-drawn sleigh rides. Those who prefer the apres ski activities to the actual skiing will be sated with the town’s dining options like the Glacier Haus and Huckleberry Inn, as well as the beers from Mt Hood Brewing Company. The Mt Hood Cultural Center educates visitors on the history of the region, as well as its geography, geology, and other interesting facts.
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Distance from Portland: Two hours
A historic fishing and cannery town located near the mouth of the Columbia, Astoria is home to some of the most treacherous shipping waters in the country. While the town’s history—which dates back far beyond Lewis and Clark or its namesake John Jacob Astor—is fascinating, you don’t need to be versed in it to enjoy your trip. Start by visiting the Astoria Column—from its base you can find a stunning view of the city, the bay, and the river. But those willing to climb the 164 steps of its winding staircase will be rewarded with an incredible view of the coast and countryside. Afterwards, head back downtown and grab a pint of Buoy beer while looking out over the river at the massive shipping vessels, catch a musical performance at Fort George Brewery, or enjoy some Bosnian food from Drina Daisy.
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Cranberry Museum
Cranberry Museum

Distance from Portland: Two hours, 15 minutes
The aptly named Long Beach in Washington features a number of destination sites that makes it worth the drive—the Cape Disappointment Lighthouse is anything but disappointing, one of the oldest lighthouses on the West Coast, and a crucial tool for the area known as the Graveyard of the Pacific. The beach, however, does live up to its name—with nearly 30 miles of unbroken sandy beach, it’s reportedly the longest beach in the country. Besides wandering the shore and exploring the surrounding woods, visitors can sample spirits from Adrift Distillery and tour the Cranberry Museum, which features cranberry bogs and history about the fruit and its role in the Pacific Northwest.
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Distance from Portland: 2 hours, 45 minutes
Not far from Sisters, Oregon, Suttle Lodge & Boathouse is a sprawling series of cushy lodges on the banks of the picturesque Suttle Lake. In winter, it’s a wonderland of pure snow and pine trees above the crystalline waters. It’s hard to beat a hot toddy or Irish coffee at Skip, the cocktail bar in the warm lodgehouse after an afternoon of snowshoeing around the pristine wilderness. Plus, the Hoodoo Ski Resort is less than 15 minutes away, making Suttle Lodge a convenient home base for a weekend of skiing on something that isn’t Mt Hood.

Yachats, Oregon
Yachats, Oregon | Emily Marie Wilson/Shutterstock

Distance from Portland: 2 hours, 55 minutes
At this point, Cannon Beach and Seaside are a given when it comes to Oregon coast trips, but Yachats is still relatively underappreciated. Forget white sand beaches or surfing, Yachats is all about untamed, primal beauty. Its incredible rocky shores are geological wonders, as well as an excellent spot for tide pooling. Be sure to take absolute caution when visiting the coast, however, and check all advisories for the chance of sneaker waves, which are deadly serious. After you’ve enjoyed the incredible coastline you can head back to the quiet town to visit the shops, galleries, and restaurants.
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Distance from Portland: Four hours, 30 minutes
Nearly at the border of California, Ashland is one of Oregon’s most well known and most visited small towns for one reason: the Oregon Shakespeare Festival. Despite the last few years, between the pandemic and brutal wildfires, OSF has had a hard time of it, yet it has persevered and is still one of the most celebrated theater companies in the world. Besides the legendary playhouses, Ashland also offers pristine wilderness to hike in, while skiers and snowboarders can hit the slopes at Mt. Ashland. Thanks to the tourism for the Shakespeare festival, the town features an abundance of dining and imbibing options, including a stunning prix-fixe menu at Mäs and cocktails and Izakaya food at Sakana.
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Seattle, Washington
Pike Place Market in Seattle, Washington | f11photo/Shutterstock

Distance from Portland: Three hours, 10 minutes
That’s right, good old Seattle—it’s a lot closer than it seems, perfect for an overnight trip or long weekend. You can go the classic route and tour the hip Capitol Hill neighborhood before visiting the iconic Pike Place Market, where vendors still toss fish through the air just across the road from the very first Starbucks. Then you can hop a ferry to Bainbridge Island to eat at the Harbor Pub. Or you can branch out, head to Ballard or Mt Baker for a weekend or visit the residential neighborhood of West Seattle with its cafes, shops, and condo-lined waterfront; it’s relatively easy to access from the south via I-5. Wherever you end up exploring, a weekend trip to Seattle is the perfect way to remember how much you prefer living in Portland.
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Distance from Portland: Five hours, 45 minutes
Oregon is replete with stunning and beautiful lakes, and while Crater Lake may get the most attention, Wallowa Lake should not be overlooked. It’s especially stunning in winter, surrounded by snow. The park has yurts and campsites offered year-round, but those looking for more amenities can find them at Wallowa Lake Resort or Wallowa Lake Lodge. Nearby is the charming town of Joseph, named for Chief Joseph of the Nez Pierce tribe—it’s perfect for quiet getaways from the city with its cafes, restaurant, and the surrounding wilderness. Fans of Oregon beers can find Terminal Gravity Brewery just a few more miles up the road in Enterprise.
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Bend Oregon
Bend, Oregon | Visit Bend Oregon

Distance from Portland: Three hours, 15 minutes
Bend may be Oregon’s favorite vacation destination due to the sheer amount of outdoor activities available year round. In the winter, it’s all about the snowy hobbies, from downhill to cross-country skiing as well as snowshoeing, snowmobiling, sledding, and tubbing. But even those who prefer a quiet night in to a busy outdoor day will find the town appealing, especially if that night includes in a beer or two: Bend is also famous for its breweries like Boneyard, Deschutes, Bend Brewing Company, and Crux Fermentation.
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Distance from Portland: 14 minutes (depending on traffic)
Does it really count as a road trip if it’s just across the river, and when thousands of Portlanders commute every day for work, and vice versa? We’ll let you be the judge—the point is that Vancouver offers its own exciting scene away from the familiarity of your habitual Portland haunts. Perhaps most exciting is the rapidly developing waterfront area with its numerous bars and restaurants offering a view of the other side of the mighty Columbia River. Just don’t let on that you’re visiting from Portland.
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Alex Frane is a contributor for Thrillist.