Two-Hour Tourist: Portland

My first impression of Portland, when I was there a few days ago to read at Powell's, was this: Portland is satisfyingly Portland, in the same way that Rome is satisfyingly Rome. Except that where Rome has its gelaterias; its ancient ruins; its manic drivers; its Gucci-wearing, impeccably coiffed, effortlessly glamorous passersby, Portland has its brew pubs; its green space; its fixed-gear bikes; its stripe-wearing, elaborately tattooed, calculatedly disheveled citizens.

There was a sad lack of flannel and beards at my reading,
though. Photo by Jessica Spiegel of WhyGo Italy.

I didn't have much time to be a tourist and see the sites, just a few hours. But it's not a big city, and I had a ringer to show me around, my awesome friend Celeste Brash, Lonely Planet guidebook writer, blogger extraordinaire, and all-purpose good company. She picked me up from the train station and said that she was working on a downtown Portland walking tour for an upcoming Lonely Planet book. Would I like to walk the route with her as she planned it out? Um, yes. Please.

I won't list everything we did and I won't reveal the particular walking route—obviously, I don't want to poach her guidebook material. But if and when you head to Portland, do go find the latest Lonely Planet and follow her suggestions. The itinerary really does make for an excellent introduction to the city, hitting the waterfront, downtown, and the three major food groups: beer, caffeine, and grease.

In the spirit of my earlier Two-Hour Tourist post, about Chicago, here's my own suggested list of things to do if you only have two hours in Portland.

First of all, get downtown. The Max light rail is your best way into the city from the airport, and to connect to various points around the city. It's always better to spend a limited amount of time exploring on foot and getting a snapshot of a particular area than trying to hop around the city by train or bus or car, seeing things only for a few fleeting moments. So: downtown.

Start your tour with some fortifications and a glimpse of a true stereotype-fulfilling Portland-ness at Voodoo Doughnuts. The line can be long—Celeste and I were there on a Friday around 3pm, and even then the queue ran out the door—but the time passes quickly because the scene offers some stellar free entertainment. There's the people-watching which is extraordinary—lots of the aforementioned stripe-wearing, elaborately tattooed, calculatedly disheveled citizens, plus all manner of other people whose attire and hairdos makes mild-mannered Midwesterners instinctively mutter, “That's interesting.” There's also the rotating case of doughnuts (like the rotating case that displays pies in an old-school diner), which include your standard raised glazed rings but also others covered in Fruit Loops or topped with bacon or filled with mango. There's a voodoo doll doughnut, naturally—a Long John with little appendages and filled with something red, served with a pretzel stick in lieu of a needle—and another called the Cock and Balls (not kidding and not asking for any more details). Throughout Portland, you see signs and bumper stickers that say, “Keep Portland Weird,” and Voodoo Doughnuts seems like the standard-bearer for that weirdness—and just to be clear, I love it so for that very reason.

And how are the doughnuts? Oh, right. Good question. They're outstanding: pillowy and not overly greasy or cloyingly sweet. If they'd been part of the Doughnut Quest a couple of years ago, I suspect they would have placed just behind the Doughnut Plant in terms of pure deliciousness. Plus, you know, style points for the performance-art bizarreness of the menu and a certain portion of the staff and clientele.

Moving on. Your appetite sated, waddle over to Gov. Tom McCall Waterfront Park for a stroll along the Willamette River. Sit on a bench and watch the parade of passersby. (Actually, what you should do is get your doughnuts to go and then eat in the park. I can think of no finer introduction to a city; in fact, without even planning it, when I'm in a new place, I somehow always find myself in a park eating a pastry.)

After you've gotten your fill of nature, wander back into downtown, through Pioneer Square—a public space that functions as the living room of the city—and end up at Powell's. You know Powell's, yes? The huge bookstore? It's … well, yes, huge. Enchantingly so, like an endless magical forest of books. They shelve both new and used books together, so there's a wonderful mix of literature from various eras, like at the library. Seriously, it's mesmerizing, the way the rooms and shelves and books just go on forever. The travel section alone is the size of many small bookstores (and since you asked, my book is in the “Travel memoirs—Europe” section …).

Your time is probably getting short now, so move along to one last stop. If you live in a major American city, you've probably noticed that food trucks are becoming, officially, A Thing. I don't just mean hotdog carts and jingle-blaring vans from which sketchy-looking dudes sell melting Bomb Pops. I mean mobile kitchens proffering actual food, restaurant-worthy food. Anyway, in Portland, food trucks are a genuinely big deal, more than just a passing trend. They're ubiquitous, and there are even some places around the city where there are five six or a dozen or more parked more or less permanently on an otherwise vacant lot, forming a food court far more eclectic and affordable and delicious than anything you'll find at even the most offbeat mall. I got some delicious tacos for $1.50 each, after considering other trucks proffering burgers and Indian curries and pad thai and crepes and—not making this up—escargot and foie gras. Yeah. From a food cart.

It's a weird and wonderful place, Portland. Truly.