Why To Spend a Week Road Tripping Across Oregon

Becca Blond

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Poppy amidst the tulips in OregonBecca Blond

From sage covered desert where rainy days are few and far between; to a rugged coastline where the Pacific Ocean meets lush old growth forest; and in the middle a verdant valley known for producing top quality wine and in spring fields of tulips, Oregon is a wonderfully diverse state that makes for a perfect week long road trip. Here we tell you why heading from the coast to the desert makes for an epic summer adventure.

Begin by the Ocean

Oregon is home to more than 350-miles of coastline, but Cannon Beach is one of the most beautiful locations in the state. Here you’ll find the towering monolith that is Haystack Rock. The 235-foot sea stack rises out of the Pacific Ocean’s crashing waves at high tide, but is accessible by food during low tide, when the water recedes beyond it and you’ll find tidal pools filled with sea stars and pink anemones.

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Sunset at the Stephanie Inn on Cannon BeachBecca Blond

Book an ocean-view room at The Stephanie Inn for at least two nights to start your trip. These come with private balconies that face Haystack Rock. The sunsets are spectacular and the rooms feature some great amenities including Jacuzzi bathtubs, gas fireplaces and a complimentary breakfast that can be taken in their dining room or on your balcony (highly recommend the later). For a classic elegant dining experience, book a meal at The Stephanie Inn Dining Room. There are two evening settings for the chef’s tasting menu that changes nightly but always includes a meat, fish or seafood option and vegetarian selection.

Another more casual dining choice is The Wayfarer Restaurant & Lounge, which offers a large seafood focused menu and extensive wine list. If you enjoy craft beer, pay a visit to Public Coast Brewing Co. They feature a dozen on-tap choices including a few different IPAs. They also serve a casual pub grub style menu including solid fish tacos.

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Ecola State Park, OregonBecca Blond

Whatever you do, don’t skip a hike in Ecola State Park. Just a few minutes outside town, the park is home to moss covered, old growth forests and awesome ocean views. The most popular trail takes you from Ecola Point down to Indian Beach. It is a moderate out-and-back hike. Make sure to bring lots of water and sturdy shoes. The ground can be soft and slippery, there are hurdles like tree trunks to clamor over and the way back is all uphill. But the views are stunning and it’s well worth the effort.

Taste Wine in the Valley

It is a three hour drive from Cannon Beach to Eugene, your base for exploring the Willamette Valley. The region is home to 70 percent of the state’s population, its six largest cities and more than 700 wineries. Nestled between the Oregon Coast Range and the Cascade Range with the Willamette River running through the middle, this valley is prime grape growing land thanks to a Mediterranean climate and dramatic temperature swings between day and night (but usually staying above freezing year-round).

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Oregon wine countryBecca Blond

The valley’s southern wineries, closer to Eugene, are actually our favorites. They are less crowded than the northern wineries that attract more crowds visiting from Portland and home to some unique venues. Pay a visit to Left Coast Estate in Rickreall. The 500-acre property is best known for its pinots and chardonnays, which are the two dominate grapes throughout the valley.

A family owned winery, we love Left Coast’s commitment to sustainable and responsible wine production and land restoration. They also produce some really excellent wines — try Suzanne’s Reserve Chardonnay that can be sampled onsite. Excellent wood-fired pizzas are also served.

Another favorite family run venture we discovered is Bluebird Hill Cellars in the town of Monroe. A relatively small operation that began as a hobby vineyard less than 10-years-ago, today it is producing award-winning bottles with some scoring up to 94 points from Wine Enthusiast. The small-batch wines are produced onsite in a converted garage attached to the owner’s hilltop house with a large, covered porch and nearby pergola where you can order tasting flights and cheese and charcuterie platters.

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The Gordon Hotel in EugeneBecca Blond

At the bottom of the valley is the college town of Eugene, where we recommend basing yourself for exploring this region. The Gordon Hotel is where to stay. This new art-forward property anchors the also just-opened Market Alley, which is also home to the flagship Nike store (the brand was born in Eugene).

The boutique hotel is an artistic stunner with more than 250 pieces of original art hanging in public spaces and the rooms and suites. Inside the lobby area, which features a fantastic ceiling of hanging mason jars and a video installation, there is a fully stocked “Art Bar,” where you can let your creative side loose using their paint, pencils, canvases and other artist supplies, for free.

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French bistro fare at Marche in EugeneBecca Blond

While in town make sure to grab dinner at Marché, which is just a few minutes away from the hotel in the 5th Street Public Market that is also home to local boutiques and other eateries. Begin with the oysters and move on to French bistro fare.

For breakfast, try the Morning Glory Cafe. The restaurant focuses on vegan and vegetarian fare with a lot of plant-based breakfast meat choices that taste like the real deal. Other good dining choices in Eugene include Tacovore, which does Mexican-street style tacos and a variety of margaritas.

End in the Desert

With 300 days of sunshine per year, Oregon’s high desert around Bend is the perfect ending spot for your road-trip — even if you are greeted with rain on other parts of your journey, you’ll more than likely find sunny blue skies here.

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Sahalie Falls in OregonBecca Blond

And the drive to get here from the Willamette Valley is nothing short of spectacular. Head east, across the Cascades on 126-E. Most of the drive is scenic, but there are a few must-stops. The first is Sahalie Falls, about an hour and a half into the drive. The falls are located just a few steps from a small parking lot on the side of the road and the walk down to them feels like entering a parallel universe. Surrounded by lush green vegetation and usually inclusive of a rainbow, the gushing waterfall is well worth a stop.

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Clear Lake, OregonBecca Blond

Also be sure to pause a few more miles down the road at Clear Lake. The transparent emerald and turquoise hued lake looks like a tropical sea and feels out of place against a landscape of fir trees and snowcapped peaks, which makes it all the more magical. Pack a picnic and sit by the shore or rent a rowboat to see the lake from a different perspective.

Once you’ve crossed the mountains the landscape changes again to the sage and juniper cloaked high desert that’s home to your final destination, Brasada Ranch. Located about 30-minutes from Bend, this gorgeous property sits on nearly 2,000 acres of land and is home to a mix of 65 luxury cabins dotted around its golf course and a handful of adults-only suites in the Ranch House. The cabins are dog and kid friendly and with 2 to 4 bedrooms perfect for multi-generational vacations. They come with full kitchens and private hot tubs and grills on spacious decks.

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Brasada RanchBecca Blond

There is plenty to keep you busy here for at least two nights, but we’d recommend three if you have some extra time. The ranch is home to an 18-hole golf course where no two holes run parallel to each other and each offers gorgeous mountain and desert views. It also boasts an equestrian center where you can book a morning or afternoon trail-ride. These are customizable to your skill level — so if you aren’t a total beginner you won’t just be stuck walking the entire ride — and lessons are also offered.

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Dinner at Range Restaurant at Brasada RanchBecca Blond

Grab dinner at the onsite Ranch House or Range Restaurant. Both serve seasonal ranch-to-table fare and the Range Restaurant in particular offers breathtaking sunsets that set the sky ablaze in orange, pink and purple and seem to go on for hours. It is the perfect way to wrap a vacation.

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Becca Blond is an award-winning travel and lifestyle writer with a focus on luxury and adventure travel, travel with dogs and mental health. She is the author of more than 30 Lonely Planet travel guides across five continents. Her work has also appeared in US Weekly, The Los Angeles Times, The Denver Post, The Points Guy, Thrillist, Afar Magazine, Matador Network, Culture Trip, Trivago Magazine and many others. Before joining the travel writing world she was a breaking news reporter for the Colorado Springs Gazette. She lives in Denver, Colorado and travels the world monthly with her service dog Poppy.

Denver, CO
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