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Many people arrive in Portland with visions of Portlandia in their minds. And while Oregon’s biggest city certainly does benefit from the vibe created by the free thinkers, eco-warriors, and chilled out artisans satirized by the infamous Fred Armisen and Carrie Brownstein show (sup’ cute coffee shops!), it’s worth keeping in mind that pop culture only tells a sliver of the story.
Tucked in the Pacific Northwest, just below the Washington state boarder, Portland benefits from relatively mild winters and temperate summers, so there’s rarely a bad time to visit—provided you don’t mind your seasons being served with a side of rain. Citizens are fairly in touch with the environment, since no matter how far you stay into the concrete jungle, there’s a quick escape into nature. It's a benefit that has helped the city attract the most athletic apparel and outdoor recreation companies in the United States. Need a jogging or biking buddy? You can probably find one. If you’re feeling ambitious, you can even bike to the Portland International airport and leave your ride at a rack out front. (Just be sure to snap a photo of the ugly/iconic carpet as you leave.)
If your sense of adventure is more highball than hiking, you can find plenty to do without leaving the city limits. Window shop in the Alberta Arts district. Switch from coffee at Smiths to tea and sample brews at Tea Chai Te. Tap into your artsy side at ADX Portland, a collective work space that offers tools to those interested in learning wood or metal working, jewelry design, or printmaking without high entry fees. (They also offer one-off learning classes, so check out their course catalogue.) Finally, if all else fails, toast to your trip and sample a local favorite, like the women-owned Freehand Spirits or Vinn Distillery, which boasts the only Chinese maker on Portland’s Distillery Row, or the LGBTQ-friendly Santé Bar.
Not totally sure where to start? We’ve got you covered. Here’s an introduction to some of the city’s most interesting, Instagrammable, and just plain fun locations.
Find the White Stag Sign
Are you even in Portland if you don’t snap the city’s iconic welcome sign? Having repped everything from sugar to specialty goods, it became the city’s local welcome sign after the city bought the property in 2009 and changed the lettering. If you visit around Christmas, be sure to snap a photo as the white stag magically transforms to Rudolph the red-nosed reindeer. Bonus: Voodoo Donuts is located right down the street. Do with this information what you will.
Go to Pittock Mansion
Pittock Mansion is an impressive 46-room estate located in the West Hills area of Portland. Even if you’re not an architecture-head with taste for French chateau vibes and well-kept flower gardens, it’s still an obligatory visit for the best overlooks in the city and all five of the major cascade mountains. (That would be Mount Hood, Mount St. Helens, Mount Adams, Mount Rainer, and Mount Jefferson.) Picnics are encouraged, so toast to a vibrant sunset or nibble on a not-so-sneaky snack while you enjoy the view.
Hike to the Witch’s Castle
There’s a lot of green stuff surrounding the city. (No, we’re not talking about weed, although that’s legal as well.) Portland specializes in nature and local green spaces like Forest Park has over 70 miles of trails, so it's quite possible to disappear into the wilderness at least for a bit. But you don’t have to be angling for a Wild experience to get your fill. For a less challenging but certainly rewarding walk in the woods, point your feet in the direction of the Witch’s Castle. Located on Lower Macleay Trail, the hike will take you about a half-mile into the storybook-worthy woods (pictured) to former bathroom facilities reclaimed by nature and steeped in local lore. (Not pictured—it’s worth seeing for yourself.) Is it the scene of violent murders and witchery or just a local hangout that's a pretty place to rest your feet? Who can say?
Explore the Portland Japanese Garden
If dirty hiking shoes aren’t your thing, get your fill of nature at the Portland Japanese Gardens. The immaculately manicured 5.5-acre garden is a dream for plant lovers—lush and green in the summer, and a riot of red, orange, and yellow in autumn. Slow your heart rate and breathe in as you stare into the zen rock garden, admire the ponds thick with koi, and wander through pathways lined with bonsai trees. Then recharge with tea at Umami Café, a building with a design inspired by Kyoto’s Kiyomizu-dera temple.
Eat as Much as Humanly Possible
You don’t have to eat upscale food to enjoy memorable food experiences in Portland. (Though given that chefs like Naomi Pomeroy of Ripe Collective and Sam Smith of Tusk call Portland home, you can certainly get your fill of high-end eats.) For less budget-busting options, head to one of the city’s many food cart pods. Nosh on traditional Japanese sandwiches at Katsu Sando, crunch a traditional Chinese crepe at Bing Mi, or fall face first into local produce at Farmer and The Beast.
Just don’t forget dessert! Portland is a donut town—and while you’re likely to upset a local, it’s worth it to swing by Voodoo for one of its iconic pink boxes. Just be sure to save room for Blue Star, which has made a name for itself with its complex "donuts for adults" flavors, which have included Blueberry Bourbon Basil, Cointreau Crème Brûlée, and Raspberry Rosemary Buttermilk. Finally, add some ice cream to this obscene sugar buzz with Salt and Straw, a local favorite that specializes in complex seasonal flavors, vegan options, and unlimited taste tests. (COVID permitting.)
Snap Street Art
While you can’t always put a bird on it, artists in Portland have managed to create masterpieces just about everywhere. While some have a permanent home, like the Velvet Underground/art fills the void tribute (SE 12th & Division street) or the Untitled flying old woman (412 SW 12th Ave), others can be an elusive find. For updated lists, and even a functional map, be sure to check out Street Art in Portland.
Shop Local at Powell’s Books
If reading makes you more attractive, then Powell’s might be the sexiest place in town. (Apologies to Portland’s vegan strip club.) Powell's City of Books' flagship location (1005 W. Burnside St.) is the largest independent bookstore in the world. Wander the city block-sized shop, snap a selfie of the iconic sign, and turn your reading list into an armful of books. Keep an eye out for its special events and cheeky staircase motivational messages. (Sample spotting: "What do Walt Whitman, Gertrude Stein, Beatrix Potter, and D.H. Lawrence have in common? They’re all self-published. Are you next?")
Stay at a Cute Hotel
As one of the original homes of Ace Hotel, Portland knows a thing or two about artsy digs. Cuddle up at The Hoxton, the iconic British hotel’s second location in the U.S., which features artwork from local curator Upfor. Take yourself back to elementary school with McMenamins Kennedy School, an Art Nouveau-style school building repurposed to feature 57 boutique hotel rooms and an on-site brewery. Or just chill out at Hotel Lucia (pictured above), a 1909 landmark hotel with a modern, Instagram-worthy lobby.
If you've fallen in love with Portland, book a trip here.
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