• Image about Northeast Portland''s Kennedy School

In Portland, it’s always-available candy-covered doughnuts, endless free games of Ms. Pac-Man and never, ever having to grow up.

THERE AREN’T MANY taboos in Portland, Ore. Yet in writing this article, I’m violating a major, unwritten rule of the city I now call home: Never tell the outside world what Portland is really like. Doubt me? Well, get this: Contrary to popular belief, Portland, Maine, averages more annual precipitation than Oregon’s largest city. And speaking of the East Coast, while many regard Portlanders as cabin-dwelling fleece monsters, this Pacific Northwest burg is among the top five cities with the most LEED-certified structures per capita in the United States. Portland is also the worldwide nerve center for Nike and Columbia Sportswear — and it’s also the North American headquarters of Adidas. So, in reality, Portlanders are actually highly skilled innovators, swaddled in Gore-Tex and moisture-wicking fabrics.

But this misinformation campaign has a purpose. Portland is a real-life Neverland where adults can play all they want and (almost) never have to grow up. The people of this carefree city tend to eschew corporately contrived entertainment and create unique forms of amusement on their own. For example, they’ve turned an abandoned school into a beer drinker’s Eden, launched their own no-holds-barred sports league and booked a calendar full of colorful events that you won’t find anywhere else. And since making Portland such an enjoyable place can be hard work, it’s understandable that locals don’t want outsiders coming in and stealing all the fun.

But this is one secret that’s too good to keep. Just remember — you didn’t hear it from me.


Portland teems with inventive and unique lodging options, but if you’re looking to recapture your childhood, McMenamins Kennedy School is the only place worth hanging your hoodie. A former elementary school converted into a hotel/bar/restaurant/movie theater complex, Northeast Portland’s Kennedy School is one of many properties developed by the McMenamin brothers, owners of an outfit that specializes in reclaiming unused structures and adorning them with whimsical, Grateful Dead-esque decor.

Like much of Portland — or Beervana, as it’s sometimes called — the McMenamin empire revolves around microbrews, and guests can drink their way from the Honors Bar to Detention to the Boiler Room without getting in trouble with the principal. Hotel suites have been constructed in former classrooms, full restaurants now occupy the cafeteria and the boiler room, an on-site brewery is in what was once the girls’ restroom, and second-run movies are shown in the auditorium each night. But don’t be surprised to see kids running around without a hall pass — even though this is a grown-up playground, it’s also very family friendly. www.kennedyschool.com

Food & Drink

Breakfast: A novel, new eatery on Portland’s lauded culinary scene, Slappy Cakes allows diners to cook their own pancakes on griddles built right into the table. The concept is not only fun but tasty, with various batters and toppings to choose from. Here’s the catch: The regular menu, which includes an array of eggs Benedict and other first-meal favorites, is even tastier. www.slappycakes.com

Lunch: Locals go loco for Portland’s food cart scene, but visitors tend to be skeptical of eating from a “roach coach.” Exercise some child like naïveté at the Grilled Cheese Grill and be wowed by sumptuous-yet-simple sandwiches. Whether it’s the Pre-Schooler (American or cheddar, white or wheat, no crust) or the B.A.B.S. (bacon, apple, blue cheese and swiss on rye), it all goes well with a Capri Sun in their retrofitted-school-bus dining room. www.grilledcheesegrill.com

Dinner: While the dank, cavernous Le Bistro Montage specializes in odd Cajun delicacies like frog legs and gator bites, the extensive menu of mac and cheese will make the young’un in you yelp. And, leftovers — if there are any — get foil-wrapped into the shape of various objects (a flower, a sword, a squirrel, etc.) just because it’s fun. www.montageportland.com

Late night: The downtown Portland location of Voodoo Doughnut is open 24 hours a day, but you’re likely to find a line outside when the bars let out because tipsy barflies love noshing on inventive confections like the Neapolitan (a chocolate doughnut with vanilla frosting and Strawberry Quik). But revelers best make sure you’re only saying “I do” to eating another doughnut: Voodoo also conducts fully legal wedding ceremonies, so make sure your beer goggles are stowed, lest you make a love connection while waiting in line. www.voodoodoughnut.com


Games: Before adults got stranded at button-pushing day jobs, many delighted in banging on the control pads of classics like Frogger and Galaga. Downtown Portland’s Ground Kontrol Classic Arcade has herded a bunch of electric antiques of the 1970s, ’80s and ’90s into this two-story gaming gallery, where they usher out the under-21 set after 5 p.m. so the arcade can serve beer and liquor. And the last Wednesday of each month features a “free play” night, where you can leave your quarters at home and play Donkey Kong until you drop. www.groundkontrol.com

Spectator Sports: Beauty, brawn, babes — the Rose City Rollers unapologetically peddle these three killer B’s to sports fans of Portland with a flat-track roller- derby league that empowers women, thrills crowds and supports charitable causes. Featuring a local league as well as supporting traveling all-star squads, the Rollers battle fast and furiously, with teams whipping skaters around the track. The players, with creative monikers like Cher the Pain and Hurricane Skatrina, are quite colorful, often with lots of ink and eccentric hair colors. But the game is about more than just elbows and hip-checks — the Rollers’ strategy and speed always have the crowd on their feet. www.rosecityrollers.com

Amusement Parks: Perhaps the best place in Portland to recapture that childlike wonder is Oaks Park, a seasonal, old-school midway that looks like it’s right out of the movie Big. One of the oldest continually operating amusement parks in the country, Oaks forgoes the g-force-crushing contraptions found in most modern parks for crowd-pleasers like the Ferris wheel, tilt-awhirl and the merry-go-round. Oaks’ old-school roller rink is also open year-round and features a great old Wurlitzer pipe organ, to the delight of skaters young and old. www.oakspark.com