Two days and too much to see — that’s the battle cry of many a traveler. Luckily, Portland is easy to traverse and has plenty of attractions convenient to its city center. Make the most of your spin through Stumptown with this 48-hour plan.
Day One: Walk Through Northwest Portland
On your first day in town, explore the central city’s northwest quadrant to get a feel for our diverse neighborhoods.
Old Town Chinatown
You’ll burn plenty of calories on this adventure, so don’t be shy with the breakfast menu at Bijou Cafe, a Portland institution that’s been slinging oyster omelets and tofu scrambles for 35 years. It’s only a three-block jaunt to Portland Saturday Market (also open Sundays), where artisans sell local, hand-crafted goods that include jewelry, pottery and clothes.
If you’ve been bit by the shopping bug, walk up West Burnside Street to Powell’s City of Books, which, with 3,500 different sections, is the world’s largest independent bookstore.
Or, if you’re shopped out, take a short detour into the Old Town Chinatown district, where the Lan Su Chinese Garden carves a walled sanctuary out of an entire block, offering visitors a Zen-filled escape.
After enjoying the garden’s leafy trees or leafing through books, head back to the bricks to explore the Pearl District. A former industrial area, this neighborhood is now home to boutiques, galleries, restaurants and cocktail lounges. Make your way north and enjoy the people watching at Jamison Square.
If you’re ready to tap into Portland’s famed microbrew scene, head to Deschutes Brewery & Public House. The state’s largest craft beer producer, Central-Oregon-based Deschutes has been a Pearl District staple since 2008. Order the sampler tray to taste a variety of beers, some available only at this location.
Next, head west (either on foot or by streetcar) to Northwest Portland/Nob Hill. A tree-lined street with some of the city’s tiniest shops and eateries, Northwest 23rd Avenue is perfect for a leisurely stroll, but don’t resist the temptation of happy hour specials and dinner menus along the way. Neighborhood favorites include Olympia Provisions NW, which serves up finger-licking snacks like fried almonds and marinated olives; Northwest 21st’s Paley’s Place is helmed by an acclaimed local chef and specializes in Pacific Northwest fare; and Bamboo Sushi, which serves the most eco-friendly Japanese dishes you’ll find anywhere.
Goose Hollow or West End
Finally, it’s time for evening entertainment — and almost no part of the city gets livelier than Goose Hollow and Downtown Portland’s West End. From Northwest Portland, it’s a short walk south to Providence Park, home of the Portland Timbers soccer team, or east to the Crystal Ballroom, which hosts major concerts and frequent themed dance parties.
If there’s no more bounce left in your step, a movie at Living Room Theaters is in order. With art films, popular movies, cocktails and food, this comfortable movie house close to Powell’s will even let you put your feet up.
Sports fans, theater lovers and vegan foodies flock to this Southwest Portland district.
The chic Pearl District features galleries and cultural institutions, as well as stylish shops and acclaimed eateries.
Northwest Portland offers sophisticated shopping, dining and people-watching.
Day Two: Hit the Heights
Spend your second day discovering some of Portland’s most acclaimed destinations, including multiple family-friendly museums and a massive park that is home to several of the city’s most beloved attractions.
Museums for All Ages
Alternatively, it’s only a half-mile stroll downtown to the Portland Art Museum, where Native, modern and contemporary art have inspired visitors since 1892.
Spend the afternoon in Washington Park, a 160-acre wonderland with multiple attractions that could each fill up a day. It’s easiest to take MAX (Portland’s light rail public transit system) to the park’s west edge, where the World Forestry Center and Oregon Zoo pull together educational exhibits that kids will never forget.
The park’s east side can be reached on foot or by bus from downtown Portland, and is home to the peaceful International Rose Test Garden and stunning Portland Japanese Garden, both of which are impeccably maintained and perfect for capturing quiet moments of reflection – and great skyline views.
Dinner and Dessert
For more inspiring sights, head back downtown for dinner at Portland City Grill or Departure, where the sky-high views will put your two days crisscrossing the city in perspective. Or visit Higgins Restaurant or Clyde Common, where the focus is on delectable regional fare and expertly crafted cocktails.
Wherever you eat, be sure to leave room for dessert at Voodoo Doughnut — their colorful, sugar-coated treats are available 24 hours a day, so their Old Town shop makes a great final stop, whenever your evening or trip comes to an end.
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Removed Portland Walking Tours due to closure. [IW 12/29/20] Let someone else do the driving while you enjoy wine tasting and vineyard views.
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