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10 Dreamy Winter Drives in Oregon to Explore This Season

  |  Cannon Beach, Central Oregon, Hood River, Neighborhood Insight, Portland

With soaring mountains, sweeping vistas, sandy beaches and azure skies, Oregon in the summer is a dream. But after Labor Day, when the day-trippers start to stay home and the Californians flock back south, our state transforms into a different kind of destination completely.

Come winter, a blanket of gray pulls up and covers the coast, bringing with it drizzly rain, strong storm surges and crashing waves. Snow comes to Central Oregon, making our iconic mountains stand out even more. Our waterfalls freeze, our vast valleys become dusted with white, and our landscape somehow becomes even prettier than it was in the warmer months.

If you want to get a peek into how gorgeous Oregon is in the winter, we’ve rounded up a few dreamy scenic drives for you to go on this season. From long coast treks to meandering valley drives, we’ve got them all right here!

During the winter, local roads may be covered in snow or ice. We recommend checking road conditions before heading out. You can see a list of current Oregon road conditions and closures here.


Otter Crest Loop

Distance: 4.2 Miles

Nestled right on the edge of Highway 101 on the Oregon Coast, Otter Crest Loop is a blink-and-you-might-miss-it hidden gem. While it’s a pretty short detour, it’s well worth it, offering some incredible views of snow-capped geological formations, bridges and other notable landmarks. The loop itself climbs over the 500-foot Cape Foulweather and guides visitors past the Ben Jones Bridge and the Devil’s Punchbowl—which is even prettier during the colder months when it fills with water after winter storms. Offering several spots to pull off and stop, this special 4.2-mile road is also a great spot to enjoy winter whale watching away from large crowds!


Portland to Timberline Lodge

Distance: 66 Miles

Offering some of the best skiing, snowboarding and tubing in the state, the Timberline Lodge on Mt. Hood is one of our favorite winter destinations. But it isn’t just the lodge that gets us excited to head over to Government Camp, it’s the incredible sights along the drive! The trek from Portland to Timberline Lodge over part of the Mt. Hood Scenic Byway will take you through the towns of Sandy, Cherryville and Mt. Hood Village, passes by sky-high Douglas Firs, and features breathtaking views of a snow-covered Mt. Hood.


Historic Columbia River Highway

Distance: 75 Miles

We couldn’t possibly leave the Historic Columbia River Highway, one of the most scenic drives in the entire country, off of this list! This 70+ mile highway is pretty iconic, giving you the chance to discover waterfalls, historic monuments, fish hatcheries and a number of jaw-dropping overlooks. But out of all the amazing stops along this historic drive, you don’t want to miss Multnomah Falls, which just happens to be the most-visited natural recreation site in the Pacific Northwest. In the winter, this breathtaking natural beauty becomes a winter wonderland, with water falling past snow and ice-covered rocks and splashing onto a glittering frozen pool. Trust us, you’ll want to bring a camera for this one!


McKenzie Pass-Santiam Pass Scenic Byway

Distance: 82 Miles

The McKenzie Pass–Santiam Pass Scenic Byway travels over two passes in the Cascade Mountains. The 82-mile loop starting and ending in Sisters can be conquered in just a couple of hours and while most people like to visit during the summer and fall, driving through during winter offers its own charm and beauty! You’ll find a little bit of everything along the way, including ancient lava flows, waterfalls, old-growth forests, mountains, rivers and more, all glistening with some signature Oregon winter fog and snow.


Bend to Crater Lake

Distance: 102 Miles

What is a great drive without an amazing destination? This 102-mile drive from Bend to Crater Lake not only offers gorgeous winter views, but ends at one of the Pacific Northwest’s most renowned sights. With a depth of 1,943 feet, the magnificent Crater Lake is the deepest lake in the United States. Because of its depth, the lake rarely ever freezes, which means you’ll be greeted with a bright blue lake against a backdrop of snow-capped hills and trees when you visit this winter.


Oregon Outback Scenic Byway

Distance: 171 Miles

The Outback Scenic Byway takes you through a slice of the Great Basin Region, capturing our state’s rugged and diverse landscape. As you push south along the byway, lush green forests in the shadow of the Cascades are replaced by sagebrush and rock formations as far as the eye can see. In the winter, those rock formations are usually sprinkled with snow and you’ll be greeted with icy ponds and frozen sagebrush that will crunch underfoot. If you get chilly, head to the Summer Lake Hot Springs, which lies about halfway through the byway and features several steaming hot springs for you to relax in!


Rogue-Umpqua Scenic Byway

Distance: 172 Miles

For a tour of some of the state’s most gorgeous frozen waterfalls, look no further than the Rogue Umpqua Scenic Byway. Most of this 172-mile scenic byway runs along the gorgeous Umpqua River and ends at the scenic Rogue River.  Between the two points, you’ll find plenty of great winter hiking opportunities, stunning views, frosty evergreens and countless waterfalls. If you want to add a little more excitement to the trip, take a detour to the south entrance of Crater Lake, which is open year-round!


The Journey Through Time Scenic Byway

Distance: 286 Miles

The Journey Through Time Scenic Byway stretches 286-miles through north-central to eastern Oregon, beginning in the community of Biggs and ending in Baker City. The road meanders through ghost towns and small farming communities that bring the Old West to life, with the Wild and Scenic John Day River, North America’s second longest undammed river, parallels most of the route! Driving along this iconic byway during winter offers the chance to see bright red rocks contrasting with pure white snow, with views of gently sloping hills and soaring mountains dusted with frost in the distance. Because this drive passes through several remote areas, you’ll want to be sure to have a full tank of gas and plenty of snacks and water in case of an emergency.


Pacific Coast Scenic Byway

Distance: 363 Miles

One of the most essential Oregon drives on this list, the Pacific Coast Scenic Byway runs all the way from Astoria to the Oregon-California border, offering up some of the most jaw-dropping sights in the country. The byway offers breathtaking views of the freezing ocean while you traverse through marshes, seaside cliffs, agricultural valleys and wind-sculpted dunes. The northern portion, which runs through towns like Astoria, Seaside, Cannon Beach, Manzanita, Tillamook and others, offers a rugged and rocky landscape complete with Oregon’s signature fog. The southern half is gentler, featuring flatter beaches and farmland. During the winter this portion is actually fairly warm due to the Brookings Effect, where warm winds blow from the Chetco River, offering up balmy weather that you don’t even have to bundle up for!


Happy Exploring!

Oregon has so much to offer winter explorers. What drive do you plan on completing first? Let us know in the comments below!

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About the Author

Melissa Peterson, Director of Agent Services and Technology

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