How to Visit Oregon Like an Oregonian

Oregon isn’t a destination, it’s a way of life. Sure, it has its fair share of must-do moments and Instagram-approved itineraries. But some of the state’s most rewarding moments come from a more serendipitous approach to exploration.

Oregonians themselves see the world differently – perhaps it’s their pioneering past, or their commitment to all things local and authentic. Maybe it’s their sense of humour and fondness for the offbeat.

Want to get into the spirit? Here are some pointers on how to tour the state like a local and soak in the best it has to offer.

Create time for chitchat

Oregonians are famously friendly and love talking about where they live. It won’t be long before someone strikes up a conversation, but you can make the first move by creating opportunities to meet locals yourself.

On the coast, you’ll find people eager to share their expertise in Pacific pastimes such as kayaking and crabbing. In the outskirts of Portland you can dine alfresco at a farm, sharing a table with fellow foodies. Further afield, stay at a ranch and become part of the family. On the Umatilla Indian Reservation near Pendleton, there’s a whole museum devoted to Native American culture and tribal stories. At state parks and forests, hundreds of rangers provide insights into the area’s natural history.

Don’t be shy – the more people you encounter, the more you’ll get a feel for what makes the state tick. In Oregon, there are as many cool stories as there are people to tell them.

Try something new

At the heart of many an Oregonian, regardless of age, is an adventurous spirit. One of the state’s most successful companies, Nike, built a global brand on the phrase “Just do it.” Since new experiences are among the best aspects of travelling, why not try your hand at an activity you’re unlikely to find back home?

The city of Bend is a good hub for all things adventurous, including spelunking and river tubing. Among family friendly highlights is the Paulina Plunge, a guided downhill mountain biking trail with stops at six waterfalls. You’ll get to slide off the edge of two of them – it’s safe and not as terrifying as it sounds.

For an otherworldly experience, head to the Oregon Dunes, where desert-like landscapes stretch all the way to the ocean. It's a prime spot for sandboarding or a dune buggy tour, and the thrill of tearing across the sand at high speeds is hard to beat.

Drink local

Sure, you can buy German beer, but that’s not what Oregonians are drinking. More than 60% of draft brews consumed in Oregon comes from one of the state’s hundreds of breweries (Portland alone has more than any other city on earth). Jump on the bandwagon and discover a world of experimental hops, ale trails, sustainable suds, farm-produced batches and other chilled, micro-brewed wonders.

The same can be said for wine. Oregon produces globally recognized pinot noir in the Willamette Valley (pronounce it “Will-AM-it” to earn local brownie points), while Bend and southern Oregon also have emerging wine regions. Going on a wine tour is a great way to meet the producers, taste some tipple and pick up a couple bottles to bring back home.

Summon your inner cowboy (or cowgirl)

In the early 1800s, Oregon played a key part in American history as the destination for explorers Lewis and Clark, followed by thousands of pilgrims migrating from Missouri. Without western expansion along the Oregon trail, there would be no United States as we know it today.

Oregonians are proud of this legacy, which lives on in places such as Pendleton. The moment you hit downtown, you’ll find evidence of the old west – play the part by getting fitted for a custom-made hat, then head down to Hamley Saloon for a drink at its 100-year-old mahogany bar. Bonus points for visiting in September, when the city hosts one of the country’s largest rodeos.

Further south in Baker City is the National Historic Oregon Trail Interpretive Center, where the past comes to life through multimedia displays and theatrical presentations. Here, you’ll find covered wagons, an old gold mine, Native American artifacts and other remnants of the pioneer era.

Shop differently (and tax-free)

Forget big box stores and fast fashion; if you want to shop like an Oregonian seek out the rare, bespoke or handmade. Portland elevates shopping for one-of-a-kind items to an art form, and since there’s no sales tax, it needn’t burn a hole in your pocket.

Start at Portland Saturday Market, a top draw for tourists and locals that’s arguably poorly named, since it’s open Sundays too. Here you’ll find everything from oil paintings to organic dog treats to handcrafted musical instruments. Even if you’re not buying, take time to chat with the artisans and get a sense of the “maker culture” many Oregonians cherish.

A short walk away, Powell’s City of Books spans an entire block and claims to be the largest independent bookstore in the world. You can get lost for an entire afternoon amid its thousands of volumes – many are second hand, including rare, obscure or autographed tomes.

Fashionistas should make a beeline for Xtabay, “the most premium of Portland’s many vintage boutiques” (Conde Nast Traveller). It’s the kind of place that dresses Hollywood stars and brides-to-be, though you’re just as likely to find an understated summer gown amid its curated collection.

Walk on a volcano

Oregonians love the outdoors, and for good reason – the state has no shortage of epic backdrops. Pack a water bottle, put on some good shoes and join in the fun.

Mount Hood, a popular spot for Portland day-trippers, is the site of the Timberline Trail, a 65-kilometre loop around the base of an 11,240-foot volcano. It can take three to five days to complete the whole thing, but we’ll forgive you if you opt to just explore it for just an hour or two.

 Sticking with the volcanic theme, head south to Crater Lake National Park (pictured above). Around 8,000 years ago it was the site of Mount Mazama, which exploded so forcefully it caved in upon itself. The resulting hole filled with snow and rain, creating the deepest lake in the United States. In summer months you can catch a boat to Wizard Island, a cylinder cone on the lake, and hike to the top for unmatched views of brilliant blue surrounds.

Embrace the weird

If you’ve ever seen an episode of Portlandia, you’ll be aware of the “keep Portland weird” mantra. We'd argue the penchant for the unusual extends statewide.

Lean into eccentricity by visiting attractions such as the large The Simpsons-themed mural in Springfield the Willamette Valley. There are more than 30 towns with the same name in the U.S, but this is the only place to be endorsed by the show’s creator Matt Groening as “the real Springfield.” You can even whet your whistle at the local “Moe’s Tavern” after an afternoon of touring.

In Astoria, just across the bridge from Washington state, a 1920s bank building houses the Museum of Whimsy. You'll either love or hate its quirky collection, but it’s impossible to remain indifferent to all the wax statues, taxidermized animals, lifelike dolls and other curiosities on display.

If you’re travelling with kids, consider a stop at Prehistoric Gardens, a coastal attraction located within an actual rainforest. It’s like Jurassic Park, but with a lower chance of being eaten – a walking trail winds past 23 life-size dinosaur replicas, lovingly sculpted based on measurements from fossil skeletons.

Thinking of going to Oregon? You’re not alone. Canadians represent the biggest contingent of international tourists to the state. Air Canada flies nonstop to Portland from Calgary, Toronto and Vancouver. WestJet is running daily Calgary-Portland flights in spring and summer. Or you can drive down from Vancouver in under seven hours. Visit Travel Oregon to start planning your trip.