You could spend your entire life in Oregon and never run out of places to explore. The state is like a Choose Your Own Adventure book of endless possibilities. There are vineyards, sandy ocean beaches, dazzling cities, dense forests, mountains, and deserts, all within a few hours’ drive. However, you’ll want to immerse yourself in one destination at a time to make the most of your visit.
To help you with your planning, we’ve gathered a list of the best places in Oregon in the winter, focusing on stunning and unique destinations that’ll have you planning your next trip before you even leave. Luckily, Oregon is amazing year-round.
Portland
Portland, Oregon Landmark White Stag Sign With Blue Sky
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Despite being home to more than 600,000 people, Portland is a lush city filled with trees, parks, and open spaces. The Columbia and Willamette rivers move through like glittering highways, combining beautiful vistas with recreational activities like kayaking, fishing, and boating beneath the city skyline. Be sure to bring your appetite, because the food scene in Portland is legendary.
Base yourself at the lovely Porter Portland Hotel, and you can walk to popular attractions like the riverwalk at Governor Tom McCall Waterfront Park and Keller Auditorium, where you can take in everything from concerts to Broadway plays. And don’t miss the opportunity to wander the aisles at the world’s largest used and new bookstore, Powell’s City of Books (it takes up an entire city block)!
Beer culture runs as strong as the mighty Columbia River in Portland, so grab a pint (or two) at one of the city’s many breweries. Oregon’s first brewpub, McMenamins, has locations scattered in funky, historic buildings throughout the city. Portland is also famous for its vibrant food cart scene, featuring almost every type of food imaginable, alongside upscale restaurants like Tusk, where Middle Eastern and Mediterranean cuisine meet the fresh ingredients of the Pacific Northwest.
Ashland
Snow covered landscape in Ashland Oregon
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Ashland is most famous for hosting the Tony Award-winning Oregon Shakespeare Festival. Since it was founded in 1935, the festival has grown to a nearly year-round event encompassing Shakespeare, modern classics, and new works in state-of-the-art theaters and pop-up venues throughout town.
Lest you think that Ashland is just for theater lovers, let us remind you that this is Oregon, and the outdoor recreation is as much of a draw as the theaters. The Upper Klamath and Rogue River are some of the premier rafting destinations in the country.
In winter, head to Mt. Ashland for skiing or walk through the 93-acre Lithia Park, which is somehow even more beautiful with a dusting of snow.
If you stay at the beautiful and historic Winchester Inn, you’ll be right downtown to explore charming downtown Ashland and walk to theaters, shops, restaurants, and Lithia Park.
Willamette Valley Wine Country
In this Oregon scene, snow-covered Mt Hood sits on the horizon behind rolling hills covered in vineyards.
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Willamette Valley Wine Country is 150 miles long and 60 miles wide. There are over 700 wineries, meaning you can take countless trips to Oregon Wine Country and have a completely different experience each time. Forest Grove is less than an hour’s drive from Portland, but the lush vineyards and farmland make you feel like you’re worlds away from the city. Standout tasting rooms here include David Hill Vineyard and Winery, located in a more than a century-old farmhouse, and Sake One, one of the only sake distilleries in the U.S.
The best part? In winter, you can enjoy Oregon Wine Country without throngs of tourists.
Some of the best tasting rooms in Oregon are in and around Carlton, including Resonance Wines, which is famous for its Burgundy-style pinot and chardonnay. For a truly unforgettable experience, book one of the refurbished retro trailers at The Vintages Trailer Resort, where funky aesthetics are combined with luxury amenities.
Cannon Beach and Seaside
Haystack Rock in Cannon Beach early morning sunrise. The sun glowing on the rock and its reflection in the wet sand.
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The Oregon Coast is rugged, unspoiled, and thankfully, the state has committed to keeping all beaches open to the public. The most iconic landmark is Haystack Rock, an awe-inspiring 235-foot sea stack stretching toward the sky just off the coast of Cannon Beach. It’s a beautiful backdrop for photos, but an excellent place for nature watching, especially when the Tufted Puffins are there between April and early September.
Cannon Beach is also home to the Stephanie Inn, which is located right on the beach with stellar views of Haystack Rock. It’s arguably the finest hotel on the Oregon Coast if you aren’t spending the night, at least stop by for a meal because the restaurant is a worthy destination.
In winter, you’ll practically have the beach to yourself. If you’re looking for family fun, drive a few miles up the coast to Seaside, where you can walk the promenade to the aquarium, arcade, and sweetshops to keep the kiddos entertained.
Crater Lake National Park
Rim Overlook at Crater Lake National Park in Oregon, USA
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Imagine the bluest blue you’ve ever seen. Now imagine something even bluer. This is the color of Crater Lake, where the waters are so beautiful they put sapphires to shame. Formed when a peak collapsed during a volcanic eruption 7,700 years ago, it’s the country’s deepest lake and one of the most pristine. The lake has a small island in the middle, and it’s hugged by cliffs two thousand feet high.
Crater Lake National Park is Oregon’s only National Park. It has spectacular hiking trails, scenic roads, viewpoints, old-growth forests, and fascinating visitor centers. Crater Lake Lodge is over 100 years old, filled with history and breathtaking water views. Typically open from May through October, it’s also a great place to grab a drink or a meal if you’re just visiting the park for the day.
Crater Lake National Park is open in winter, though roads are limited in winter. It’s the perfect time for snowshoeing and exploring without the crowds.
Astoria
Astoria, Oregon
Astoria is located just before the Columbia River meets the Pacific Ocean. You can easily spend a day doing nothing but watching cruise ships and barges as they pull in from the Pacific. The town is full of old-time charm with colorful Victorian-era houses, an old-time trolley rolling along the riverfront, and docks where fishing boats unload their catch at the end of the day.
If you think Astoria looks familiar, it’s probably because the town was made famous in movies like Kindergarten Cop and The Goonies. You can learn all about it at the Oregon Film Museum, which is housed in the historic building that served as the jailhouse in The Goonies.
Other must-visit stops in Oregon include the Columbia River Maritime Museum and the Astoria Column, a nearly century-old tower perched on a bluff over town covered in art depicting the area’s history. You’ll have to walk up 164 steps to get to the top, but the jaw-dropping vistas of the Columbia River and Pacific Ocean are worth it.
If you’re staying overnight, or even longer, the Cannery Pier Hotel and Spa is built over the Columbia River, and the rooms are as beautiful as the views.
Mt. Hood National Forest
Spectacular views from area of Timberline lodge in Mt Hood National forest, Oregon, USA
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Mt. Hood National Forest contains over a million acres of scenic forests, streams, lakes, and Mount Hood, the tallest mountain in Oregon. In the snowy season, there are more than 32 slopes for skiing and snowboarding, but it’s also an incredible destination year-round for hiking and climbing.
You’ll love staying at the historic Timberline Lodge. The building served as the exterior for The Overlook Hotel in The Shining, but there’s nothing spooky about the spectacular views of Mt. Hood or the gorgeous rustic interior. In the warmer season, soak in the vistas from the Magic Mile SkyRide to a viewpoint 7,0000 feet high on Mt. Hood.
No matter what time of year you visit, the area’s natural beauty is something you’ll carry with you for the rest of your life.
Bend
Three people bundled in snow gear snowshoe in a forest as snow falls around them.
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Bend combines the cultural amenities of a large city like Portland with some of the best outdoor recreation in the country. Seriously, there is almost nothing you can’t do here. In winter, visitors flock to the area to ski the majestic Mount Bachelor or snowshoe the Edison Butte Sno Park slopes. In summer, the Deschutes River attracts inner-tubers, rafters, anglers, and kayakers. And those are just the above-ground activities. Bend is home to a system of below-ground lava tubes formed by ancient volcanoes, so caving is also popular here.
The high desert climate is sunnier and drier than cities like Portland, to the west of the mountain, which makes outdoor dining here a must. Many restaurants have outdoor patios where you can sit in the sun and fire pits to warm yourself on cooler days. Bend is particularly well-known for its breweries and distilleries. So, save time for a trip to the Crater Lake Spirits Distillery Tasting Room and their next-door neighbor, the Deschutes Brewery and Public House. When you’re finished, spend the afternoon checking out the murals and public art as you meander through the boutiques downtown.
To make the most of your Bend experience, stay at Brasada Ranch, a resort with fantastic views outside of town where you can choose between private cabins or luxurious rooms in the lodge.