Here’s the thing about this laid-back seaport city nestled in the shadow of Oregon’s majestic Mount Hood. To really enjoy it, it’s best to go native.
Portland, to quote our Uber driver, has “a very chill vibe.” So to get your panties in a twist because, say, you happened to arrive on one of the coldest days in recent memory (14 degrees) is counter productive. Why worry about frostbite when there’s a Stumptown Coffee adjoining your hotel, and a warm bag of cinnamon sugar doughnuts (cash only) awaits you at the original Voodoo Doughnuts on Southwest Third Avenue?
Are you really going to fret about not being able to hike to the top of Oregon’s tallest waterfall, Multnomah Falls, because it unexpectedly snowed, when there’s so many craft breweries and independent distillers that demand attention? A very cool whiskey movement is taking shape these days in Portland, and at places like Labrewatory, a North Portland “craft beer lab,” you can wet your whistle with cutting-edge (and weird) brews such as Billy the Squid, a cherry gose darkened with black squid ink.
And who cares if an impending ice storm threatens to delay your flight home when the eighth wonder of the world — Powell’s City of Books — is open until 11 p.m.? A mecca for book lovers and the largest independent bookstore on the planet, this temple to print stretches over an entire city block. It’s so big, visitors use fold-up maps to negotiate its color-coded rooms. Weather be damned; you can happily get lost in there for hours. Even if you haven’t visited (in my case, for journalistic research) one of the 160-plus recreational marijuana dispensaries within the city limits beforehand.
Relax, people, and go with the flow.
Known as much for its lovely parks and gardens as its many outdoor adventures along the scenic Columbia River Gorge, Portland might seem an odd destination in winter. And truth be told, had a doctor’s appointment not brought us to the Pacific Northwest in January, we, too, would have planned our trip for summer.
Yet other than some cold toes and a bummer of a red-eye flight back home that took off four hours late at 3 a.m., we had a blast.
We started our adventure late on a Wednesday, with much-needed pints of local fave Breakside IPA at Clyde Common off the lobby of Ace Hotel. (It’s a long flight from Pittsburgh.) While dinner there came highly recommended, we weren’t up for a formal meal and headed instead to Sizzle Pie, known for its rockin’ meat, vegan and veggie pizzas and vegan salads. Go for the 6 Degrees of Kevin Bacon, a tasty combination of Canadian bacon and pineapple — it’s an awesome welcome.
Our lofty introduction to Oregon Health & Science University’s main campus on “Pill Hill” was quite magnificent, too. The Portland Aerial Tram ($4.55 round trip) ferries commuters 3,000 feet from the city’s South Waterfront district to the charming Marquam Hill neighborhood. The 4-minute ride, 175 feet in the air, is thrilling in itself, but it’s the view from the upper deck that really blows you away. On a clear day, you can see Mount Hood and Mount St. Helens in the distance, as well as the city spread out below you.
The scenery is equally spectacular from the eastern lawn of the Pittock Mansion. Built in 1914 for Georgiana and Henry Pittock, monied owner of The Oregonian newspaper, the 46-room French Renaissance-style chateau sits 1,000 feet above sea level two miles west of downtown and offers a sweeping vista of five volcanic peaks in the Cascade Range. The mansion was dark ($10/adults) the day we visited — the publicly owned landmark is open for tours February through December — but the sprawling grounds and surrounding trails in Macleay Park are worth your time.
A ready tourist, I’d read up on the city’s hot spots and planned many of our adventures in the Pearl District. Once home to warehouses and light industry, the area today is a treasure trove of art galleries, restaurants and cool boutiques. It was easy to fill most of a day seeing the sights, stopping for a sip here and a bite there. We lunched at Grassa, a communal Italian restaurant serving handmade pastas, and ate swanky bar snacks at Kask; experienced happy hour at Multnomah Whiskey Bar and broadened our beer education with a sampler paddle at Deschutes Brewery Pub; and filled up on charcuterie at Oven & Shaker. We also spent a merry hour at Pine Street Market, a new food hall in the historic Baggage & Carriage Building. Settled in at the OP Wurst stall, we paired artisan Pineapple Poke Dogs with a puckery pickleback, a shot of whiskey followed by a shot of pickle brine (my first). A nightcap at Pepe le Moko, a subterranean speakeasy near the Ace Hotel, bid the night farewell.
We also marveled over the city’s many food trucks (more than 600 citywide), especially the 10th and Alder pod, a collection of about 30 food carts at Southwest 10th Avenue and Southwest Alder Street.
Yet there’s more to the city than just food and drink.
Remember that talk about Portland being chill? We got some of our best travel ideas from the 20-something “bud tender” behind the counter at Nectar on Mississippi, a cannabis shop across the Willamette River in the Boise neighborhood.
Hearing we were from out of town, he ticked off a list of places not to be missed and even sketched us a map: the many cascading waterfalls along the historic Columbia River Highway, most notably Multnomah Falls, the most visited natural recreation site in the Pacific Northwest. The McMenamins Kennedy School near the Alberta Arts District, a 1915 elementary school-turned-entertainment center. We definitely needed to stroll through the Hawthorne district, home to funky vintage stores, restaurants, pubs and coffee shops — including one in a double-decker bus.
“Be sure to take the cool way” to the falls along Route 30, he advised us, instead of the “rookie way” on Interstate 84. And once on Hawthorne, we were to seriously consider de-stressing in a salt-water sensory deprivation chamber at Float On, a float tank center. And if we only had one drink at Kennedy School, make sure it was in the multilevel Boiler Room bar, where mechanical equipment once hummed with activity and children clapped erasers.
He also told us to look for the Tilikum Crossing foot bridge at nightfall. The sole bridge in the country dedicated to light rail, buses, bicycles and pedestrians, it’s covered in LED lights that change color and speed up or slow down depending on how fast, deep and cold the Willamette River is flowing.
We took all of the kid’s suggestions and had such a time of it that when we learned the day of our return that bad weather was moving in, we even revisited one of them.
Along with three of the coolest bars you’ll ever encounter, the Kennedy School boasts a boutique hotel with rooms in former classrooms, a $4 movie theater, an outdoor heated soaking pool for which there's always a line, and a brewery in what was once the girls lavatory. With ice and snow piling up outside, it proved the perfect place to kill more than eight hours as we waited to see if we’d ever get back to Pittsburgh.
If you go
If you plan on exploring sites outside the city limits, you’ll probably want to rent a car (overnight parking in city lots is about $15). If not, Portland boasts a light rail system (trimet.org) that can get you from the airport to downtown in 38 minutes and costs $2.50; there’s even a display of public art on the Red Line. The 12-mile drive from the airport, alternatively, takes about a half-hour.
Where to stay: Downtown Portland features all the usual suspects for those looking to splurge (Marriott, Kimpton, Westin) or pinch pennies (Econo Lodge, Travelodge). If you’re keen on the hip factor, the Ace Hotel ($125 and up) — where haircuts are free in the lobby the first Thursday of the month and some rooms come outfitted with record players — won’t disappoint. The McMenamins Crystal Hotel ($125 and up, pet-friendly rooms available) is equally funky, with colorful rooms that feature handpainted headboards and wall inspired by rock songs. If you don’t mind not being downtown, the Tiny House Hotel in the Alberta Arts District is as cool as they come — it features six one-of-kind tiny houses (120 to 170 square feet) clustered around a courtyard with a fire pit. The rate ($155 and up) includes all-you-can-eat s’mores. Lodging at The Kennedy School, a remodeled elementary school, includes rooms in old classrooms. Rates start at $135 and guests receive complimentary use of the soaking pool and free admission to the movie theater.
Food and drink: Portland is a gourmand’s dream, offering everything from fine dining to soup and noodle houses to gourmet pizza shops, brewpubs and barbecue joints. Portlanders also take pride in their food trucks, a coffee culture that celebrates independent roasters (Stumptown is a local fave) and cool coffee shops and marijuana dispensaries. Pine Street Market features nine of the city’s best chefs and purveyors, including OP Wurst. And definitely taste-test Voodoo Doughnut against competitor Blue Star Donuts.
Activities: Portland has something for just about everyone. If you love beer or whiskey, there are more than a dozen breweries, wineries and distilleries. If you’re into art, the Pearl District is a hotbed of galleries. Definitely plan a visit to Powell’s City of Books, billed as the world’s largest used and new bookstore. In nice weather, there’s biking through BIKETOWN, the city’s bike share system (a day pass costs $12), parks and gardens, kayaking on the Willamette River and hiking on the Intertwine or nearby Columbia River Gorge, which offers some of the most beautiful waterfalls in the U.S.