48 Hours In: Portland, Oregon

by Nicola Brown · October 25, 2016

Portland is a West Coast city like no other in the United States. It lives up to the signs and bumper stickers that proudly state “Keep Portland Weird!” with every quirky stripey knee-high sock and eccentric T-shirt. Portlanders definitely live life to the beat of their own drum, and they take their thriving small-batch craft and maker cultures seriously. Here’s how to spend 48 hours in this unique city.

What to See

Somewhat to my surprise the first recommendation I received in Portland was to visit the bookstore. But this isn’t just any bookstore. It claims to be the largest new and used bookstore in the world. Powell’s City of Books stretches an entire city block and 3 stories upwards with shelves upon shelves of new and used books side by side. You could spend hours here, and people do, curled up in corners buried in pages.

Portland bikes. Credit: Abi Porter, Flickr

One of the best ways to get a feel for Portland is to hop on a bike. It’s a super environmentally conscious city and a perfect bike-friendly city to explore. Pick up some wheels from the city-wide bikeshare racks or head to Pedal Bike Tours for a guided tour.

One of the great things about Portland is how close it is to outdoor adventure in Oregon. Just half an hour away you can reach Mt. Hood, a year-round destination for hiking, mountain biking, kayaking, skiing and snowshoeing to name a few. Dinner at Silcox Hut, a rustic outpost 7000 feet up the mountain is a truly memorable experience.

Raptor Ridge Winery. Credit: Nicola Brown

Wine lovers can head to Raptor Ridge Winery in Newberg for an open-air lunch and some glasses of exceptional Pinot Noir overlooking a gorgeous sloping valley of vines.

Back in the city, a visit to the International Rose Test Garden, home to 10,000 roses, is a must. It started as a safe haven for hybrid roses grown in Europe during World War 1. The garden is a heavenly oasis of smells in the summer, and it’s where Portland gets its nickname the City of Roses. It also offers some of the best views you can get over the city.

On Saturdays head to the Portland Saturday Market and Portland Farmers Market for a true taste of local life, then get your hands dirty with a screenprinting workshop at ADX, a collaboration hub for local artists and designers to share tools, knowledge and experience. Here you’ll discover the true makers’ culture Portlanders are so proud of.

What to Eat

Portland food trucks. Credit: Markus Spiering, Flickr

Portland is home to a wonderful trend: food truck pods. With over 600 food trucks to choose from throughout the city, you’re spoiled for choice. And the food isn’t the drab, questionable hot dogs or styrofoam boxes of mystery sludge you might think of as food truck food. Portland’s food trucks serve up some of the best artisanal and gourmet food in the city, and you can get everything from Thai to South American fare, and everything in between. Because of the high prices of bricks-and-mortar locations, you’ll find all the new chefs and emerging food trends in these food trucks. Food truck pods are a great place to meet locals too, as communal seating amidst the clusters of trucks brings everyone together to eat their food.

Portland loves its brunch, too, but make sure to get to your brunch spot early. Many people wait for hours outside their favourite local haunts starting as early as 8 or 9 in the morning. Mother’s Bistro is a local favourite for traditional home cooking.

Multnomah Whiskey Library in Portland. Credit: Nicola Brown

If it’s a night out you’re looking for Portland is flush with lively drinking establishments to suit all tastes. Head to the Multnomah Whiskey Library for an overwhelming selection of 1,500 different whiskeys (it’s hard to get in when the library’s members are in town but worth adding your name to the waitlist anyway). Or see what the city’s extensive craft beer scene looks like with a Brewvana tour of the city’s top breweries and cideries.

Where to Stay

Jupiter Hotel in Portland. Credit: ken tam, Flickr

The Jupiter Hotel is a quirky boutique spot in a converted midcentury motor lodge that channels the Portland vibe perfectly. You’ll find chalkboards on the back of the hotel room doors so you can embrace your artsy side and personalize your decor. Rooms are designed with a minimal but chic aesthetic that reflects the effortless cool of the city. There’s live music by local bands almost every day just next door at the Doug Fir Restaurant, and the hotel is also home to an art gallery. When you’re ready to explore the city try out some of the alternative eco-friendly options offered by the hotel: Electra bikes and pedicabs, anyone? And yes, you can even bring your pets!

While the rest of the world tries to copy hipster trends on an industrial level, Portland sticks firmly and authentically to its small-scale eccentricities. It has none of the pretentiousness and all of the genuine individuality and community-focus of a place that’s still true to its quirky roots.

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Nicola Brown

Owner & Principal at Think Forward Communication

Nicola is an international award-winning writer, editor and communication consultant based in Toronto. She has travelled to 32 countries so far and is always poised to head out the door again. Nicola loves both the visceral and intellectual dimensions of travel, and will passionately argue for its psychological paybacks, especially after a few glasses of wine. She lives for opportunities to illuminate the life-changing power of travel for as many people as possible.