First things first: Don’t go there and expect to find Portlandia. Portland, Oregon, isn’t the city you’ve seen on the riotously funny Fred Armisen/Carrie Brownstein comedy; it is neither atavistic (the “Dream of the ’90s” is dead, son) nor inordinately weird (unless you’re kind of uptight and boring). It’s not New York with more hippies or San Francisco without hills. This charming Northwest river town, the “Rose City,” is something much more interesting than that: It is the antithesis of hot, sprawling, pedestrian-hostile Las Vegas in virtually every way.
Imagine a place that’s big enough to contain multiple neighborhoods, yet feels close and intimate. A place that’s wholly connected together by clean, safe light rail and streetcar lines. A place where daytime summer temperatures rarely crack 75 degrees. A place where delicious eats are everywhere you turn, from endless great restaurants to a legendary street-food scene. A place where there are parks—actual parks, with trees and grass!
Doesn’t that sound preferable to the hipster-infested dystopia of Portlandia? Now you know why Fred and Carrie play things so broadly: They’re trying to thin the tourist herd. If everyone knew how wonderful actual Portland is, it’d be completely overrun with the garden-variety douchebags who might have learned—and this is the truth, confirmed by Portland’s Willamette Week—that the city has more strip clubs per capita than any other American city (one club for every 9,578 residents, versus Las Vegas’ pitiful one-to-every-33,002).
Most importantly, Portland is the ultimate good hang. No matter who you are or what you’re into, it wants to be your friend. If you want to do some hiking, some of Oregon’s most picturesque trails—including Coldwater Peak, which cuts through the heart of the 1980 Mt. St. Helens “blast zone,” and the Multnomah-Wahkeena Loop, which casually rolls past 10 waterfalls as if they were no big deal at all—are within two hours’ drive. Prefer to keep your nature walks closer to your hotel room? Check out Tideman Johnson Natural Area (a nearly 8-acre park encompassing a creek gorge) and Forest Park Conservancy (with its more than 5,000 wooded acres overlooking the Willamette River), both within minutes of downtown.
Hungry? At any given time, there are more than 500 food carts on Portland’s streets, with quality ranging from “not bad” to “whoa, fuckin’-A!” Some carts are the product of chefs who once ran restaurants and now prefer the freedom of street cooking, while others belong to ascending talents destined to run restaurants of their own. (For the latest favorites, and to find out what carts are where, check out FoodCartsPortland.com). If you’d rather do “proper,” sit-down dining, just ask the cart owners and patrons for recommendations: Portlanders know their food, and they’re bracingly honest about where to get the good stuff.
There’s still more to Portland worth checking out: Terrific art galleries, quirky retail and dozens of historical buildings and sites. And, yes, recreational marijuana will become legal in Portland in July, although the first retail facility probably won’t be up and running until 2016—at which time I’ll update this article with an emphasis on available munchies.
How to get there
Alaska Airlines routinely offers competitive rates into Portland International, located minutes from the heart of the city via light rail (the MAX Red Line). Also: Be sure to snap a selfie with the airport carpet. (Google “PDX Carpet,” and you’ll understand why.)
Where to stay
If you really want to get the full flavor of Portland, try its boutique hotels. The Hotel Monaco offers super-stylish accommodations (hipster-baroque décor, in-room goldfish). A more affordable boutique experience can be had at the Jupiter Hotel, a former motel fancied up with cool art and swank midcentury furnishings. And a stay at McMenamins’ Kennedy School—a 100-year-old converted elementary school with an in-house brewery and movie theater—is unlike anything you’ve experienced.
Where to dine
In addition to the street carts, try the artisanal meat sandwiches of Lardo; Portobello Vegan Trattoria, which serves delectable versions of Italian favorites; and Pepe le Moko, which offers fresh oysters, grilled scallop escabeche, mustard braised rabbit tart and other small plates alongside well-made classic cocktails. … Get your coffee at Public Domain, and get your donuts at Blue Star instead of Voodoo; while the latter is fun and touristy, the former is where locals go.
What to do
Take a pedicab tour of Portland’s Distillery Row, a district of craft liquor distillers that features lots of free tastes and fascinating, boozy insights. … Want your berries unfermented? Check out one of the city’s farmers markets, even the smallest of which puts Las Vegas’ biggest to shame.
Anyone who simply calls Powell’s Books “a really big bookstore” hasn’t been there. It’s an awe-inspiring monument to the written word, and you can buy pieces of it to read on the plane trip home. In fact, you may want to throw out your clothes and fill your suitcase.