The Perfect Three-Day Weekend in Portland, Oregon
Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to Portland, Oregon.
If you’re looking for a weekend getaway in a place that’s relaxed, hip, and green (in more ways than one!), look no further than Portland, Oregon. The city is known for being “weird,” and you can definitely find some quirkiness in PDX if you’re looking for it, but you can also find a place that’s known for its forward-thinking chefs, talented artists, beautiful green spaces, and other attractions. It’s got a small town feel with big city amenities—it’s a one of a kind place, and there are hidden gems around every corner.
For those who are unsure how to spend three days for a vacation in Portland, have no fear! We’ve got you covered.
Day One: Northwest Portland
The PDX airport isn’t far from where all the action is, and with a short cab ride, Uber, or public-transit ride, you’ll be in the heart of it all. Stay at The Nines, right near bustling Pioneer Square, for easy access to the MAX light-rail. After you drop off your bags and get your bearings (which isn’t hard in this city—it’s basically a grid, split in half by the Willamette river), start your day at Coffeehouse Northwest, one of Portland’s many wonderful coffee shops. Once you’re caffeinated, head just a few blocks over to Powell’s Books—it’s an entire city block of books, and you can find anything you’re looking for among the shelves.
At this point you’ll have worked up an appetite, so head over to the Daily Cafe for brioche French toast or some rainbow hash. They also serve up some killer blood-orange bellinis and Bloody Marys, for those who are so inclined.
Head up to the International Rose Test Garden for some greenery. Portland is a city, sure, but it’s one that’s known for its urban green spaces and for never letting city life interfere too much with nature. Smell some flowers before heading back downtown, just in time for a sweet pick-me-up at Cupcake Jones. They have filled cupcakes and a rotating menu. You can check ahead to see what they have on the menu that day, or wait to be pleasantly surprised. End your day at Ground Kontrol, an arcade bar that is a paradise for those of us who have never really grown up.
Day Two: Northeast Portland
Northeast Portland is known among tourists mostly for its quirky artist district, Alberta. Head over to Pine State Biscuits for what’s sure to be one of the best breakfasts of your life. Their biscuits are fantastic and you can’t go wrong no matter what you order. We do, however, recommend the Reggie. After that, explore the neighborhood! There are so many boutiques in the area, like Frock, a vintage clothing store for women, Ampersand, a new and used bookstore, and Close Knit, a fantastic yarn store—and did we mention that shopping in Portland is tax-free?
After you’ve finished shopping, check out Salt & Straw, an ice cream shop unlike any other. They have regular vanilla, sure, but they also have flavors like “caramel corn on the cob” and “zucchini bread with chocolate freckles.” You’ll want to try every single flavor, if not just to see what it could possibly taste like.
Then, head over to Mississippi Avenue for some more exploring. You’ll find more great shops, restaurants, and bakeries. We recommend checking the calendar ahead of time at Mississippi Studios to see if there is a show you’re interested in seeing—even if there isn’t, it’s a great place to check out, because the attached Bar Bar is a terrific spot to grab a drink and a burger.
Day 3: Southeast Portland
First thing’s first—stop at Coava for coffee. The baristas there are knowledgeable about what they do, and since Portland is such a big coffee town it would feel wrong not to make a stop at one of the best shops they have to offer. And you’ll need that coffee, because you’re going to Screen Door for breakfast, which often has a line—but it’s so worth it. The line goes quickly and you forget all about it once you’re eating their breakfast hush puppies with bacon and cheddar, or bananas Foster French toast.
Today, you might want to spend some time just walking around the Hawthorne neighborhood. There are so many beautiful Victorian homes, and the neighborhood is gorgeous. Hawthorne also has a fun, friendly vibe that contributes a lot to how people typically think of Portland. Once you’ve seen enough of the neighborhood, you can go record shopping at Crossroads Music or Jackpot Records and shop the vintage styles Portland is known for at House of Vintage and Red Light Clothing Exchange.
If you’re all shopped out, head to dinner at the original Pok Pok, a fantastic Southeast Asian restaurant. We recommend trying their drinking vinegars, but if you want to also go out for drinks afterward, you can head right across the street to the Whiskey Soda Lounge for a nightcap (or two).
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