How to Tour Portland, Oregon

If you still picture Portland, Oregon, as a mere slacker town only inhabited by the fleece and socks-and-sandals set, prepare to be pleasantly surprised.

Known as the City of Roses, this playful place, infused with forested parks, green spaces and gardens, exudes a laid-back, alt-y vibe, an appreciation of everything drinkable and edible and the permissive nature of a still-sort-of slacker town.

It’s consistently ranked in the media as the greenest city in America, the best city for public transportation, the most bike-friendly and even the best city in which to have a baby (by Fit Pregnancy, 2008). It has a City-sanctioned “official doughnut,” an openly gay mayor (Sam Adams) and a 24-Hour Church of Elvis (a pop culture museum).

If that doesn’t convince you that Portland — a place where comedian Patton Oswalt jokes you can pay for a sandwich with a song — is worthy of checking out, then perhaps Oregon having no sales tax will. That’s right. None. Meaning the already-great deals in the city are that much better.

Where to Eat in Portland

Portland, where pioneering foodie James Beard was born and raised, has always had an appetizing food scene, largely because of the high-quality vegetables, meat, fruit, fish, cheese, beer and wine that are produced within an hour or two of the city. Combined with a critical mass of passion, skill and experience, this has resulted in an explosion of innovative restaurants throughout the city, with incredible value, to boot. 

Food carts are at the low end of the price spectrum. Many of them are actual trucks, and they’re permanently parked in pods around the city. In downtown Portland alone, there are 80 carts serving the lunchtime grab-and-go crowd. With Thai, Vietnamese, Peruvian, Japanese, Greek, Polish, Mexican and many more options, it’s a veritable United Nations of food where items average about US$5.

Another distinctive local eating experience can be had at Voodoo Doughnut, which is famous for its voodoo doll-shaped doughnut, complete with pretzel stake and dribble of jelly blood. It also did NyQuil doughnuts for a while until the health department told them to knock it off. You can even get married there with various ceremony packages available.

Le Pigeon offers gourmet French dining minus the stuffy atmosphere, with communal tables and seating at the counter overlooking the open kitchen and a menu that is creative, daring and elegant. Desserts are especially noteworthy. 

Wildwood Restaurant & Bar offers Pacific Northwest cuisine and wine at its finest in a cozy, upscale setting that’s in perfect harmony with its location near Forest Park’s Wildwood Trail. 

Andina is a contemporary Peruvian restaurant in the Pearl District that has a sexy, sultry atmosphere with a superb cocktail menu — don’t skip the pisco sours — and an extensive menu with terrific, unexpected flavour combinations. 

For fans of Japanese cuisine, Masu Sushi does artful sushi in a modern lounge with beautiful decor and great lighting.

Where to Drink in Portland

There’s beer in Portland, and plenty of it. In fact, in 1888, local brewer Henry Weinhard volunteered to pump beer from his brewery into the Skidmore Fountain at its dedication.

These days, Portland is generally regarded as America’s microbrew capital, with 28 breweries within the city.

The Oregon Brewers Guild offers a map of local breweries for visitors, and a good place to start a tasting tour is at Widmer Brothers Brewing Company, one of the city’s oldest and largest. There are free tastings and tours on weekends where you can learn all about the brewing process and sample such brews as Drop Top Amber Alem Deadlift Imperial IPA, Sunburn Summer Brew and Widmer’s most plentiful, Hefeweizen. 

Also worth a visit is BridgePort Brewing Company, which claims to be Oregon’s oldest craft brewery. It is best known for its India Pale Ale, as well as its barley wine called Old Knucklehead.

With beer comes brewpubs — cozy places with low lights, crackling fires, good food and friendly people — of which Portland also has plenty. Brothers and brewpub pioneers Mike and Brian McMenamin own 23 pubs around the city, all of which are unique. You can only get the brothers’ beers in McMenamin establishments, and their approach has been to create a European-style, community-based pub scene where children are welcome (with parents) and the atmosphere is relaxed and fun. They even have movie-theatre brewpubs in their repertoire.

But Portland’s booze scene does not thrive on beer alone, as local distillers are quietly starting a craft distillation revolution, producing whiskey, brandy, grappa, vodka, gin and even absinthe. The epicentre of this movement is in southeast Portland’s Distillery Row, where there are five distilleries: House Spirits Distillery, New Deal Distillery, Integrity Spirits, Stone Barn Brandyworks and Deco Distilling. They all offer tastings and, while the operations are modest and somewhat makeshift, they make up for it with charm and personality, especially at Integrity Spirits, where owner/distiller Rich Phillips is a storyteller extraordinaire.

In addition to its alcoholic products, Portland is a big-time coffee destination. The city is home to the original Stumptown Coffee Roasters, well known by aficionados as one of the highest quality direct-trade roasteries, as well as dozens of other micro-roasteries and cafés, where the baristas will school you on the intricacies of their brews.

Things to See and Do in Portland

There’s a strong tree-hugger contingent in Portland, and for good reason. Forest Park, the largest wooded urban park in America, located west of downtown, has more than 113 kilometres of recreational trails that draw runners, hikers, bikers and horse riders. It includes the 48-kilometre-long Wildwood Trail, a pedestrian trail that’s part of a 64-kilometre loop system. 

Or, you can check out Tom McCall Waterfront Park, Portland’s answer to Venice Beach. 

The park’s green ribbon along the west bank of the Willamette River draws walkers and bikers and, on a clear day, it provides a glorious view of Mount Hood in the distance. It’s also the site of numerous festivals, parades, performances and more.

Flower aficionados won’t want to miss the International Rose Test Garden, which was established in 1917 and is the oldest continuously operated garden of its kind in the U.S. This breeding ground for scented beauties is free and open from April through October, so visitors can stroll among 7,000 rose bushes. 

For a totally Zen escape, smack in the middle of downtown, visit the Lan Su Chinese Garden, a 40,000-square-foot, Suzhou-style garden. If you prefer a little edge and grit to your park experiences, there’s Burnside Skate Park, which was illegally built by renegade skaters and later sanctioned by the city. It’s almost hidden under the Burnside Bridge, making it hard to find, but it’s worth checking out for the crazy, humbling and inspiring skill on display.

If you're a wine enthusiast, consider heading over to the Williamette Valley to visit one of the 200 wineries in the region.

Once you’re spent from all the outdoorsy activities (or if it’s raining, as it frequently is), a visit to Powell’s City of Books is a must. This gigantic independent bookstore — the largest in the world — fills an entire city block and houses a collection of more than a million new, used and rare books. The store is located in the Pearl District, which is a superb example of a live, work and play place. Take some time exploring the shops, galleries, restaurants and bars in the area, and note the wonderful diversity of the people out and about.

Nightlife in Portland

If you want to start your evening Gus Van Sant style, head to the Nines hotel and begin with a cocktail in the comfortable library/billiard room, a place the Portland-raised filmmaker is known to frequent. It’s open to non-guests, but a better bet is just to stay at the stately Nines because it’s gorgeous. 

Later, hit up one of the city’s many music clubs where indie cred runs deep. 

The Doug Fir Restaurant & Lounge, its decor a rustic throwback to 1950s modernism, is a current hotspot where scenesters, music-lovers and ordinary folk mingle in chilled-out harmony in the upstairs restaurant, outside around fire pits or in the downstairs lounge where the bands play. The Crystal Ballroom is a fixture on the local music scene, drawing acts like The New Pornographers, The Decemberists and Pink Martini.

Those with a penchant for less is more (clothes, that is), will be happy to know Portland is widely considered to have the most strip clubs per capita in America, with more than 50 different venues. Mary’s Club, which opened in 1954, is Portland’s oldest nude entertainment establishment, and is a tempered mix of erotica and irony with scenic murals that attract almost as much attention as the dancers. Casa Diablo claims to be the world’s first vegan strip club — all skin, no meat, so to speak. And the Acropolis Steakhouse has 51 beers on tap.

Where to Stay in Portland

The aforementioned Nines recently received a major facelift, turning it into a masterpiece of elegant, contemporary decor that features an abundance of local art. It sits atop Macy’s department store in the centre of downtown. 

The 79-room Ace Hotel, where the flophouse scene from Van Sant’s acclaimed Drugstore Cowboy was filmed in 1988, features distinctive murals, vintage furnishings and, in some rooms, turntables and a vinyl collection to borrow from. The Jupiter Hotel is a modish motor inn-turned-boutique hotel. It’s attached to the Doug Fir Restaurant & Lounge and shares the same eclectic spirit.

Portland is nothing if not charming. Brimming with oddities, it can sometimes resemble a circus show as suit-wearing corporate types mingle with tattooed moms pushing strollers and unicyclists wheeling by. The beauty is that, not only does the city have something for everyone, but it welcomes everyone into its quirky mix of wit, style and taste. 

So when in Portland, take the time to stop and smell the roses in all their diverse glory.

Powell's Books photo: Kari Sullivan

Hotel photo: Kari Sullivan