The Best Winter Vacation Destinations in Oregon

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From lush forests to snowy mountains to temperate Portland, Oregon has much to offer, even in the wet and chilly months of winter. If you love to ski, you’ve come to the right place, but skiing isn’t the only way to enjoy the Beaver State. Cozy up at a mountain lodge, enjoy seafood on the coast or explore Oregon’s top cities. Expect to travel with some coats, rain gear or at least a sturdy determinedness to get a little soggy and you’re all set to go.

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    A frigid winter dawn near Pine Mountain east of Bend, Oregon, in the area known as 'The Badlands.'

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    Bend is one of Oregon’s most solid destinations in both summer and winter. The area in and around Bend is a veritable winter wonderland. Located in a high desert and surrounded by mountains, you’ll find plenty of snow—up to 30 feet per year in the mountains, but less than 30 inches in town. If a ski vacation is what you seek, then Mt. Bachelor Ski Resort is nearby. There’s also ample opportunity to go snowshoeing, rent snowmobiles or even take a dog sled ride!

    But the real perk of visiting Bend in the winter is that it’s not all about snow (unless you want it to be). Even in winter, there are plenty of hiking and biking trails with low or no snow near town. Or stay right in Bend proper and explore the many restaurants, galleries or the famous Bend Ale Trail. In a state with no shortage of breweries, Bend has more breweries per capita than anywhere else in Oregon.

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    About a half hour south of Bend is a resort so good that it deserves to be a vacation all on its own. While many of the available activities are the same as if you stay in Bend, Sunriver Resort offers resort perks to enjoy after a day spent skiing at Mt. Bachelor, or out in the snow sledding, snowshoeing, sleigh riding or dog sledding. Bonus—there’s a shuttle from the resort to Mt. Bachelor. At the end of your day, warm up in the indoor hot tub or steam room, dine at the resort’s restaurants or take some time out at the spa. It’s the perfect place to recharge in the middle of winter.

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    Mt Hood

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    If you’re in the mood for a winter vacation, snow and all, Mt. Hood is one of Oregon’s top spots to find it. Book a room at the cozy Timberline Lodgebecause there’s no finer way to enjoy a snowy vacation than to pair it with a lodge where you can curl up by a fireplace in your room in the evenings. Mt. Hood is home to not one, but five different ski resorts, including Mt. Hood Meadows, Timberline, Skibowl and Cooper Spur Mountain Resort. Beyond the resorts, there are even more snowy trail systems to snowshoe or cross-country ski, as well as tubing hills to sled or tube down a slope. You want snow, you can’t go wrong at Mt. Hood.

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    Snowfall in Portland

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    Portland’s weather stays fairly temperate all year round. So, yes, it does get a little rainy in the winter, but so long as you’ve got the right gear, there’s no reason why Portland isn’t a great winter vacation destination. While exploring the city’s amazing parks (Forest Park and Washington Park, we’re looking at you) may or may not be as enjoyable depending on the weather, the city’s amazing dining scene is just as amazing whether it’s raining or not.

    Maybe skip the food truck tour if the weather is really nasty, but book a reservation at one of Portland’s finer dining establishments and enjoy a view at a restaurant like Portland City Grill or a five-course chef’s tasting menu at Le Pigeon. Explore the city’s indoor attractions like OMSI, the Pittock Mansion or the Portland Art Museum by day, and head to a concert at a local venue by night (the Crystal Ballroom is always worth checking). Or even enjoy some tax-free shopping at the Lloyd Center. There’s plenty to do indoors inMORE

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    Cannon Beach

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    Winter is not the best time of year to visit the Oregon Coast. Whether you’re looking at Astoria or Cannon Beach or Gold Beach, count on likely a rain and wind filled vacation. Skip heading to the coast for walks on the beach unless you really enjoy sideways rain (and that’s not to say there aren’t lovely days on the coast in January and February, but statistically you’re more likely to get wind whipped).

    However, if you really just have a hankering for ocean, you don’t have to write off the Oregon Coast completely. However, plan accordingly—get a room with an ocean view. You might not want to go walking on the sand if the weather is horrible, but staring at a moody ocean while you snack on your salt water taffy can be undeniably enjoyable. Dungeness crab season also opens in the late fall each year so heading to the coast for some quality seafood near the source is also a boon. Or keep an eye on razor clamming tides and book a room with a kitchen or grill to cook up what you catch.

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    Multnomah Falls in the Columbia Gorge.

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    In the summer, Hood River is known as the windsurfing capital of the world. With its incredible winds whipping through the Columbia Gorge, windsurfing and kite surfing are big here. And while those activities mostly lose their appeal when the temperatures drop, Hood River still has plenty of chilly appeal. Like Timberline Lodge, Hood River makes a strong base for ski vacations as Mt. Hood Meadows and Cooper Spur are just an hour away. And, yes, you can still go windsurfing if you want to in the winter… nothing stops Northwesterners from enjoying the outdoors. Just be ready to suit up to stay warm!

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    Willamette Valley in winter

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    While you might think of visiting Oregon’s wine country as a summer activity, it’s not like wine stops just because the clouds come out. In fact, warming up with a glass of wine might be just what the doctor ordered when the winter blues have you down.

    Boutique hotels and bed and breakfasts dot the Willamette Valley and turn your winter vacation into a cozy get away. Look to the Black Walnut Inn if you want to combine beautiful views, top-notch culinary offerings and a vineyard on the property. Rooms come with a complimentary bottle of wine to get you started. Or if you like to pair a spa experience with your wine (and who wouldn’t!), the Allison Inn & Spa is just about perfect, offering a resort experience complete with fireplaces in the rooms, an indoor swimming pool, a full spa and an onsite restaurant where you can enjoy local wines and a farm-to-table menu.

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