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How To Do Oregon In Just Seven Days

How To Do Oregon In Just Seven Days

America is all about the road trip, its highways and byways continual inspiration for the most epic of travel tales, from Strayed’s Wild and Kerouac’s On The Road to Pirsig’s Zen and the Art of Motorcycle Maintenance. While for some, these endless stretches of shimmering asphalt are the perfect setting for drama, dreams and radical self-discovery, they also make for a pretty bitchin’ holiday.

Let’s Talk About Oregon

Sitting north of California is a magical state with no sales tax, and breweries and gourmet food aplenty. A place where nature’s bounty abounds, presenting visitors everything from high desert, coastline, waterfalls, wildlife, Indian Reservations, gorges, hot springs, mountains, craters and even legends of Bigfoot. Despite the sheer volume of awesome this state has to offer, you can manage to nail many highlights in one week while still allowing enough time to absorb each experience, and then Instagram it later. #northwestisbest.


Day 1: Portland

With the unofficial motto “Keep Portland Weird” and as the only US city ranked in Monocle’s Quality of Life Survey 2014, Portland’s charm is no secret. The quirky and creative city is known as one of the World’s Best Cycling Cities, the Best Beer Town in America, the Fittest City in America, and it’s also known for magnetising the bun-and-bearded, vegan hipsters made infamous by Portlandia. Start and finish your road trip here: it’s welcoming, it’s green, its independent spirit is infectious, and it’s so in right now.

Cycling in the City of Roses is easy and safe, and worth doing for a day before picking up your wheels. Neighbourhoods to visit are The Pearl District, Nob Hill (or NW 23rd), Alberta Arts District and Downtown, and a prance through the Rose Garden doesn’t go astray.


Portland is a foodie’s paradise no matter your budget or protein preference, and Portlandians are proud to support local produce and business. Stumptown Coffee Roasters is a sure bet, and when you need a different kind of pep in your step, get your ice-cream fix at Salt & Straw or try a Voodoo Doughnut. Powell’s City of Books is the largest new and used bookstore on the planet, read: heaven on earth for bibliophiles, and a meal at Portland’s food cart mecca is a must.


Where to stay: The Northwest Portland Hostel in Nob Hill is housed in beautiful old buildings, but why not jump on the weirdo bandwagon and look into the numerous quirky accommodation alternatives around, like converted caravans or TeePees; AirBnB is a good place to start researching. Depending on your budget, Ace Hotel Portland is iconic and the epitome of Portland cool.

Day 2: Columbia River Gorge

In what feels like an instant of leaving Portland along Interstate 84 east, the 130-kilometre long and 1200-metre-deep Columbia River Gorge turns it on with verdant greenery and impressive cliff drops. The expertly crafted highway runs through the river gorge, showcasing its many waterfalls and scenic outlooks. Your first stop is the Portland Women’s Forum State Scenic overlook at Chanticleer Point, which will surely put whatever trifle you’re going through into perspective.

At this point, you’re only 30 minutes out of Portland and there’s another must-see. A stupidly easy pull off on the Historic Columbia River Highway will bring you to the feet of the mighty, 200-metre high Multnomah Falls, the most photographed and tallest in all of Oregon. The ease of accessing these falls from the highway means crowds are always expected, but you’ll get over it when you walk up to the footbridge above the lower cascade and bask in Big Mama N’s glory. Bring a cardi, it’s fresh.


There are a few nearby hiking trails from Multnomah Falls that lead to more secluded options, such as the photogenic Fairy Falls, or Horsetail and Ponytail Falls. After a late lunch, there should be plenty of time to head south towards Mt Hood to set up camp for the night.

Camping suggestion: Kinnikinnick (Laurance Lake) Campground, Mt Hood National Forest.

Day 3: Mt Hood

Falsely touted as the second most climbed mountain in the world, year-round skiing and 95-kilometres of national forest make this beautiful peak a popular spot. Visit the historic Timberline Lodge, and hike (or take the chairlift) up towards the summit of Mt Hood for sweeping views. You can give Mt Jefferson a frosty wave in the distance, or look into skiing or snowboarding a few runs.


Warm Springs Indian Reservation

Heading south on the 26, the landscape drastically transforms from the expansive canopy of green firs and ponderosa pine to a hot and dry terrain of raw layered rock and desert peppered with tufts of sagebrush as you enter Central Oregon. Known as high desert, this particular area we pass through belongs to the Confederated Tribes of Warm Springs, including the Warm Springs, Wasco and Palute Native American tribes. You can dip in the mineral hot springs at the Kah-Nee-Ta Resort & Spa, go horseback riding, visit the museum to learn about native culture or speak to locals to get insider knowledge on some pretty incredible spots within the reservation.

Camping suggestion: Lake Simtustus, or The Cove Palisades State Park (unless given permission to access a local camping site).


 Day 4: Bend

Bend has the most breweries per capita in the state, and the locals are known as Benders. Related? Probably not. Ideal? Absolutely. Flanked by Mt Bachelor, The Three Sisters, and Mt Washington to the west, with high desert to the east (accounting for its 300 sunshine-filled days per year), Bend is a picturesque town with not a lot to complain about. Add to that the mountain biking, white water rafting, golf, fly-fishing and the fact you can visit its breweries via Cycle Pub, and you can see why locals warn visitors they may wind up moving here.

When in Bend you must enjoy a pint in one of its many renowned craft breweries, and the Crux Fermentation Project is perfect for lunch and an afternoon session sipping IPA’s in the sun.

Where to stay: Motel West, Bend.


Consider heading out for the afternoon along the Cascade Lakes Scenic Byway to see the phenomenal emerald glory that is Devils Lake. So fresh and so green, green, you have to concentrate on driving straight because the idea of bomb-diving the car into it is actually appealing. It is just beyond Mt Bachelor and there is access to multiple fantastic trails in the area from the campground.

DEVILS LAKE option 1 landscape

 Day 5: Crater Lake National Park

Just over two hours’ drive south from Bend sits the geological and volcanic wonder, Crater Lake. It is the deepest lake in the USA and seventh in the world, formed around 7,700 years ago when Mt Mazama exploded in one of the most immense geological events in human history. So much magma erupted that the mountain collapsed, creating an enormous crater that eventually filled with rain and snowfall, to form the incredibly blue water seen today. Still as a mirror with record clarity (due to the absence of inlets or outlets of external water sources), this site is continually studied for its geological wealth, and held in high spiritual regard by Native Americans to this day. After a few hours at Crater Lake, hold on for another two hours south to the lovely town of Ashland, Oregon’s southernmost city.

CRATER LAKE option 2 (1)


Ashland manages to be endearing with an elegant flair, so it comes as no surprise The Oregon Shakespeare Festival is a regular fixture in this culturally and culinary-rich town. Mountain vistas and rolling plains stretch far into the distance, but you don’t even care, because there are so many restaurants, cafes and bars that require your immediate attention. In true Oregon style, Ashland’s establishments focus on locally sourced ingredients, so splurge on a kumquat mojito at trendy The Brickroom, scarf a burger at upscale brewpub Standing Stone Brewery, down a sammich at Sammich Ashland, or for the health conscious, delight in the germinated brown rice-accompaniment of the organic wonders at Sauce.

Where to stay: The Ashland Hostel, or groups can consider a two-bedroom, two-bathroom family unit at Cedarwood Inn for a reasonable price.


Day 6 & 7: Blue River, McKenzie River, Portland

After a lazy morning in Ashland, we’re headed back north to Blue River. The Blue River area is a rich part of Oregon’s Gold Rush Era history, and nowadays a launchpad for the USA’s top mountain biking trail. The McKenzie River Trail is a difficult ride and not for amateurs. Said amateurs can still have fun though, so head over to the nearby Deer Creek natural hot springs, with the McKenzie river roaring right by it. This geothermal pool is far less crowded (and less creepy) than the popular Terwilliger/Cougar hot springs in the area, known to have men descend en masse should a fine female specimen appear.


Where to stay: McKenzie River Mountain Resort are run by great people and perfect for groups, offering entire cabins with fire pits by the river. For the adventurous, this is your opportunity to head to Bigfoot territory. Take a left off the McKenzie Highway after the bridge onto NF-739 and veer right onto NF-738, winding down rocky terrain to a secluded spot just above the rushing river, where locals say the Discovery Channel filmed their Bigfoot special.

It’s an easy drive up the I-5 back to Portland, rounding out your short-yet-jam-packed journey through wonderful Oregon. You did it. If you have a few extra days and want to see some of the stunning Oregon Coast, head northwest to Cannon Beach, just an hour and a half from downtown Portland.

Insider Tips:

– This road trip is safe through mountain passes and scenic byways, as well as ridiculously good looking, from spring through autumn. Each season comes with its own set of virtues, so plan ahead to see seasonal-specific activities in each area.

– Oregon has been known to have some pricey car rental rates, but there are ways to get around it. Returning a rental vehicle to its origin location is vastly cheaper than a one-way rental, and you can often find working promo codes online. Finding a great online rate then calling customer service can often bring extra discounts for booking over the phone. And in advance, companies have been known to offer fabled summer $1 a day specials.

– If you need camping gear but if you’re down with the Oregon spirit and don’t want to give your money to a dirty chain store, Next Adventure in Portland is a great local option to gear up, as their downstairs offers a consignment section.

(All photos by Sonia Taylor)

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