Portland, Oregon's famous Powell's City of Books (photo: Torsten Kjellstrand/Travel Portland)

The Weekender: Portland, Oregon

By Crai S. Bower

Here’s a prediction: You’ll travel no more than two blocks in Portland, Oregon before witnessing something right out of Portlandia, the hit TV show that lampoons the “Portland lifestyle.” But here’s the catch, watching that lumbersexual cycle a fixed-gear bike appointed with a hand-tooled leather craft-beer holder while you queue up to buy that vegan raspberry pistachio donut? That’s just what makes Portland so very, well, Portland!

The best perch from which to size up the city is from the Portland Japanese Garden, elevated within 162-hectare Washington Park. The sublime trails convey you past a beautiful array of waterfalls, rock gardens and bonsai, among other plantings. The “Moon Window” vista captures Portland, the Willamette River and, in the distance, Mount Hood.

In the park’s eastern shadow lie downtown attractions like the Portland Art Museum, which consistently features some of the Northwest’s most compelling exhibitions. Among its current offerings are a showcase of contemporary Native American fashion design and a survey of sculptural works by lauded Allied Works Architecture. (Both shows run to Sept. 4, 2016.)

For more active pursuits, consider a bike ride along the Willamette River Trail, or a more ambitious pedal along the Springwater Corridor, part of the “40-Mile Loop.” A number of shops, tour operators—like Cycle Portland Bike Tours—and even some hotels rent bicycles at reasonable hourly rates. Portland’s municipal bike-sharing system, Biketown, is also slated to launch in July.

Portland’s neighborhood du jour changes almost daily. The West End is popular at present; it’s transitioned from pop-up shops to an area bounteous with boutiques. The Union Way shopping arcade boasts bespoke items from the likes of Will Leather Goods and Spruce Apothecary. And if you really are in the market for a leather six-pack-holder for your bike back home, you’ll find it just a block north at MadeHerePDX, which lies across the street from the famous Powell’s City of Books on the edge of the Pearl District. The “Pearl,” which stretches north from Burnside Street, is teeming with shopaholic antidotes from fashionable jeans to stationery.

In 2005, chef Andy Ricker put street food on America’s culinary map when he launched his Thai-inspired Pok Pok in Portland’s then-remote Southeast quadrant. SE Division thrives today with the likes of Yataimura Maru by Shigezo—created to reflect a Japanese food alley—and the eclectic ice cream flavours of Salt & Straw. Division’s Tidbit Food Farm and Garden exemplifies the sprawling Portland street-food scene, with more than 20 international food carts surrounding expansive sit-down courtyard complete with fire pit.

Elsewhere, you can further ecure your Portlander status with a visit to one of two Voodoo Doughnut outposts, but Blue Star Donuts—they of the vegan raspberry pistachio treat—tastes just a little more Portland-ish. And Bistro Altabira City Tavern, atop Hotel Eastlund, provides a great menu and copious libations to complement the best sunset viewing terrace in the city.

Speaking of libations, there are, count ‘em, more than 55 breweries within Portland’s city limits—not to mention urban wineries and, of more recent vintage, two-dozen distilleries. Many of the latter are clustered along a self-designated Distillery Row, and offer drop-in tours and tastings on weekends.

Jupiter Hotel Portland Oregon
Eclectically designed guest rooms at Portland’s Jupiter Hotel (photo: Basil Photography/Travel Portland)

The Central Eastside, an industrial zone turned must-hang neighbourhood, provides one of Portland’s hottest properties, the Jupiter Hotel. More motel than boutique inn, the 80-room Jupiter features a rotating art gallery and the Doug Fir Lounge, which hosts scores of acts you’ll hear on the radio tomorrow, if not sooner.

Several major airlines offer nonstop flights between Calgary and Portland, to ensure you get to the Rose City as quickly as possible. If you’d rather spend some quality time on the road, Portland is an 11-hour drive from the Alberta border—through Montana, Idaho and Washington. Consider upgrading to a Plus or higher membership, which allows for extended towing distances, enhanced trip collision reimbursement and more. And don’t forget that your AMA membership is honoured by AAA in the U.S. Just call the number on the back of your card if find yourself in need of service.

We all know how important it is to buy medical insurance before travelling south of the border. Without coverage, an unexpected visit to a U.S. hospital could end up costing an arm and a leg (figuratively speaking, of course). Travel medical insurance from AMA Travel* can cost as little as $25 and provides emergency medical and dental coverage of up to $5 million Canadian.

*AMA Travel Insurance is underwritten by Orion Travel Insurance Company.  Certain exclusions, limitations and restrictions apply. Subject to certain terms, conditions and limitations.