If you’ve decided to go on a weekend getaway to Portland with your friends, you’ve made the right choice! Portland’s motto, after all, is Alis volat propriis — Latin for “she flies with her own wings”. There’s tons to do and places to flit from one to another here. Eat, drink, shop, stroll, sail… You might find a weekend isn’t enough for some good, serious, and delicious fun.
No worries, we’ve rounded up a few places and to-do’s for you and the gals to have a blast in Portland — in just 3 days.
Day 1
Assuming you arrived in the city in the morning, you can start the day at a Blue Star Donuts shop nearest your hotel. It’s Portland’s rising doughnut star, distinguished for its French brioche dough recipe and sophisticated flavors. Dig into a Cointreau Crème Brûlée, a brioche filled with vanilla custard, torch-fired to create a crisp candy shell. You’ll get a pipette of orange liqueur with it — squeeze that into the doughnut for a sweet, tangy, citrusy flavor. Or try the Blueberry Bourbon Basil, one of their most popular. It combines sweet blueberries with fragrant basil and a local bourbon, added for a hint of caramel depth.
Then head to the Japanese Botanical Gardens for a calming but enthralling stroll among shrubs, trees, moss, stone, sand and water landscapes. See the Cultural Village soak ins some Japanese architecture, then visit the Japanese Arts Learning Center to learn how to make ikebana flower arrangement and how to wear a yukata traditional dress. Visit their website beforehand to see what events you can participate in — lectures, tea ceremonies, gardening workshops, art performances. Then, for refreshments, you can relax at Umami Cafe which serves delectable sweets and an array of authentic Japanese teas.
Spend the rest of the day cruising Portland by boat on the beautiful Willamette River. Portland Spirit provides day tours aboard their luxurious yachts with delicious Northwestern lunch, live entertainment, and access to full beverage service.
Back on land, you can have dinner at Departure, downtown Portland’s upscale restaurant serving unique pan Asian coastal cuisine and global, exotic cocktails. Located on the 15th floor of The Nines Hotel along SW Morrison Street, it has two outdoor decks with views overlooking downtown Portland, the Willamette River, and Mt. St. Helens. Departure’s menu includes an assortment of dishes from China, Japan, Korea, Vietnam, Indonesia, and Malaysia: spring rolls, siu mai, dim sum, sushi, sashimi, grilled kushiyaki, bibimbap, wok-fired fried rice, and noodles. The bar boasts an extensive list of hand-crafted saké and shochu, representing many artisan producers. Try the Tasho Macho, Departure’s longest-surviving drink, which is an Asian fusion take on the Moscow mule.
If you leave room for dessert, go for some Salt & Straw ice cream. There are several scoop shops in Portland but if you swing by their Wiz Bang Bar at the Pine Street Market food hall, you’ll find their freshest, most unique spins on soft-serves, swirls, sundaes, and hand-dipped cones. The most popular flavors? Customers seem to always go for the Rocky Road Hot Fudge Magic Cone, Rhubarb Sour Straws, and PBJ sundae. Aside from soft-serves, Salt & Straw also offers “novelties” like choco tacolates — taco shells stuffed with ice cream, dipped in chocolate and sprinkled with nuts; “concretes”, or soft-serves blended with homemade Oreos, chocolate chip cookie dough, hazelnut butter crunch bars, and house candies; ice cream sandwiches, floats, shakes, and sodas.
Day 2
If you can skip breakfast and choose brunch instead, check out Tasty N Daughters (formerly Tasty N Sons) tavern on SE Division Street, a popular brunch spot offering diverse international dishes. The signature blockbuster shakshuka, an Israeli tomato-pepper stew, is highly recommended by owner-chef John Gorman. So is their Burmese red pork stew. Gorman is famous for his first huge Spanish hit, Toro Bravo, less than a mile away. He now dishes out a lot of Turkish recipes at TnD, like the pide (flatbread) with baked egg, feta, red peppers and onion; and the manti (pasta pockets or dumplings) filled with beef and lamb in garlic yogurt sauce and smoky urfa pepper.
Don’t feel guilty. Afterward, you can burn those calories shopping at Pearl District, Portland’s playground for shopaholics, art collectors and foodies. You’ll find popular women’s fashion boutiques Garnish and House of Lolo, home-grown in Portland. As are outdoor outfitters Popina Swim and Sport, U.S. Outdoor, and global shoe brands Keen and Dr. Martens. If you’re looking for souvenirs, check out Portland Gear. The locally-owned store sells T-shirts, hoodies, jackets, caps and a variety of trendy accessories to “bring home” Portland with you.
For happy hour, catch some Cuban-meets-New Orleans vibe at trendy Palomar Bar. The cheerful place is sure to pick you up after a long day, and you can all share a plate as you sip on freshly blended, slushy daiquiris and other tropical cocktails. If you’re only having one, The Oregonian suggests a hand-shaken mulata daiquiri, an El Floridita special made with añejo rum and cacao.
Later in the evening, you can settle down to a good steak at the Ox Restaurant over at Martin Luther King Jr. Boulevard. Chefs Gabrielle and Greg Denton became James Beard Awardees for the Northwest for their work at The Ox, where their Argentinian-inspired ribs, chorizos, and seafood are cooked on a wood-fired grill. Recommended are the marrow clam chowder, beef tongue a la vinagreta, tripe and octopus, the Asado Argentino or a grilled lamb shoulder and hazelnut brown butter torte.
Day 3
Craving comfort food for breakfast? Portland is now home to Pine State Biscuit, a North Carolina native-turned-Portland legend. Their fluffy buttermilk biscuits are more than heavenly, and Esquire Magazine called their most famous sandwich, The Reggie Deluxe, one of the best in the country. The Reggie is stuffed with boneless fried chicken, heritage bacon, Tillamook cheddar and a fried egg topped with sausage gravy. Split with one of the girls if it’s too gargantuan. Or, you can go for a lighter, vegetarian option, the Moneyball — a biscuit topped with shitake mushroom gravy and a freshly cooked egg.
At PSB the coffee is by Stumptown, the orange juice organic, and the chocolate milk comes from a local chocolatier. But oh, try to go early. It’s known for ridiculously long lines. Try to get there before 9 or you’d most likely wait.
Cap the weekend by venturing outside the city on a day trip to Willamette Valley. With over 600 wineries, it’s home to some of the premier Pinot noir-producing wineries in the world — many of which are just within an hour of Portland.
Start at Ponzi Vineyards in Sherwood, one of Oregon’s oldest Pinot noir vines and recognized trailblazer in oenology. Their state-of-the-art winery and flagship tasting room sits on a Northwest-facing slope of the Chehalem Mountains, surrounded by the majestic Avellana Vineyard. Enjoy panoramic views of the vineyard and valley while enjoying table-side wine and food service, fireside seating, outdoor seating or covered terrace. There are also bocce ball courts. Winery tours are by appointment.
Bergström Winery in Newberg is also prominent, noted not just for their Pinot noir but also their Chardonnays. Their Gargantua tasting is held at the cellar of their winery, with a three-wine flight of shiraz, a library offering, and a culinary pairing of local cheeses and charcuterie.
Up the road is Adeslheim, recognized for Pinot Noir, Pinot Gris, Pinot Blanc, and Chardonnay. Aside from tastings (11 am-4 pm), they offer guided hikes through the Chehalem Mountains’ most scenic vineyards.
If you’d prefer a third-party guided tour instead, Viator offers day trips to 3 to 5 wineries along with a country-style lunch and an orientation into wine grape production.
On the Way Out
Hurrying to catch your flight? Grab a quick carry-on at Flying Elephants @PDX. The Portland deli makes great grab-and-go sandwiches, salads, sides, snacks and desserts for folks on the fly — just like you.
Featured Image by Free-Photos
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