72 Hours With a Portland Local

72 Hours With a Portland Local

My sister, Aleia, has lived in Portland for the past 12 years, which makes her a bona fide local—and me a regular visitor to a place that evolved pretty quickly from a quietly cool city to majorly hot stuff. My last trip up happened to fall on the same day that the very minor Twitter storm that broke out in response to Freda Moon’s 36 Hours in Portland piece for the New York Times.

Aleia mentioned this to me right off the bat, with a can-you-believe-that-writer huff. But since I had actually tweeted that very story that morning in a “yay, Portland!” kinda way, it made me think about our different perspectives: she as a local protective about her city—and tired of the endless hype and caricaturization that surrounds it—and me as a visitor who wants to experience as much as possible in 72 hours and, yes, looks to resources like Eater Portland and the NYT for ideas. But over the years, we’ve found a pretty sweet mix: I prod her to go to places that she might otherwise dismiss as too trendy or pricy, and she opens my eyes to cool, local places that the hot lists don’t usually surface. Here’s how it went down this time*:


I arrive, thirsty. Aleia tells me we have to hurry to get to Hi-Wheel—a mead and wine spot with a killer patio—before before Tamale Boy closes at 9 p.m. Tamale Boy shares the building with Hi-Wheel and will deliver tacos and tamales to drink with your mead or funky wine. She says the guacamole is out of this world. I’m skeptical but quickly and happily humbled by the enormous mortar and pestle that soon appears, filled with avocados, sunflower seeds, and pico de gallo. I’m especially charmed by the fact that it’s mixed tableside—you choose your level of chunkiness. We sip fizzy wine and joke about how to steal the 20-pound mortar and pestle.


Family breakfast at home (cuz why go out when your sis is a chef?). I’m craving a BLTA. Aleia decides we must have a fresh loaf of potato bread to pull this off. Enter Fressen, a German bakery that traffics in pretzels, gloriously large loaves of beer and rye breads, and a number of sausage-stuffed delights. Aleia snags one of the last loaves of potato—score!—and we roll out, munching on a slice of almond brioche.

Sufficiently carbed up, we pack up our bikes and ride out to Edgefield, a McMenamins hotel/concert venue/spa. It’s too crowded for mini golf, so we shower and queue up for our concert. It’s a beautiful, warm night and we debate about whether to buy pizza or marionberry ice cream as the music washes over us. Bliss. Afterwards, we hop in the hotel’s soaking pool and pretend to do laps in the figure eight-shaped pool as couples cuddle in the darker corners.


I am obsessed with going to Pip’s for doughnuts, and so I drag Aleia and my mom (though they’re not exactly kicking and screaming). There’s a line. But man, those tiny doughnuts—fried to order in soybean oil, then covered with nutella, or marionberry, or sea salt and honey, etc.—are light and warm and very quickly gone. The chai is spicy and not too sweet. I ask them if, as locals, they would come back: “I probably wouldn’t wait in line on a regular basis,” Aleia says. She is, however, planning to return this week for her free birthday dozen. Hmm.

We decide we need real food now. Aleia takes us to Mississippi Avenue, where the tiny Wolfs & Bears serves up the best falafel sandwich I’ve had in ages, complete with labneh, caramelized walnuts, and gorgonozola. Dy. Na. Mite.

Napping, reading, and a little Portlandia (season 5 is dismissed as “not Portland enough”) ensues. Our dinner reservation isn’t until 8:45, so we head out to St. Johns, a neighborhood I’ve always wanted spend time in. The plan is to have a drink, then walk to the St. Johns bridge and Cathedral Park. But the Leisure Public House has a bocce ball court and we quickly get caught up in battle. Somehow, I am brilliant at this game I know nothing about, and my mom and sister become fierce about trying to knock off my crown—to no avail. I am undefeatable!

Aleia and I doll up and drive out to Coquine, which popped up in a recent Eater hot list. It’s sweet and fairly empty, so they seat us early. The service is kind and the technique solid, but none of the dishes blow us away. We both agree that the spicy confit duck wings are the thing to get. The restaurant is new, so we wonder if they’re still working out the kinks. Aleia says she’d come back to give it another shot. I agree. We’re too full for dessert, but the server brings her a birthday marshmallow, which we try to toast over the candle on the table. (Um, not recommended.)

I persuade her to drop by Expatriate for a cocktail. It’s not her scene, but she admits that the drinks really are killer. A foot-high pile of the late-night nachos (made with wonton chips and lemongrass beef) sails by. We are too full to even look at them, but I make a mental promise to return.


We are not hungry in any way. In fact, it is time to climb a mountain and put all of this fuel to use. We head out to the Columbia River Gorge to hike Angel’s Rest, a five-mile trail that is all hill, glorious hill. The view of the Gorge and dense evergreens steals my breath, even on this cloudy day. Time to Instagram!

My flight leaves late in the day, which means we have time for one last meal. Post-hike, we’re craving burgers and beers so we head to the Oregon Public House, a nonprofit pub that donates its profits to more than 100 charities (you pick). We donate to the NE Portland Backpack Lunch Porgram then cheers, altruistically, to Portland and all of its creative, passionate glory.

*This is by no means an attempt to capture the whole of Portland and the author recognizes that she’s missed great swaths of the city. Apologies in advance for any unintended offense.

Want more? Check out our ultimate guide to Portland!

Aislyn Greene is the associate director of podacsts at AFAR, where she produces the Unpacked by AFAR podcast and hosts AFAR’s Travel Tales podcast. She lives on a houseboat in Sausalito.
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