Portland is a city so steeped in individuality that a TV show lovingly poking fun at it has lasted eight seasons: the hilarious, Emmy-winning Portlandia. Visiting Portland provides a chance to be a little offbeat, so branch out and try a new cuisine or explore a part of the city you wouldn’t ordinarily seek out.
From its 1840s beginning as a port town (named not for the port but after Portland, Maine) near the end of the Oregon Trail, the timber industry built the town’s economy. In fact, it was originally called Stumptown or The Clearing.
You might start your exploration at Forest Park, an enormous wilderness park with more than 80 miles of trails. Another park worth visiting is Mt. Tabor Park, located on the site of a volcanic cinder cone and featuring a statue cast by the Mount Rushmore sculptor. The Portland Japanese Garden is considered one of the most authentic Japanese gardens outside of Japan. From here, it’s a short walk to the nearby International Rose Test Garden, where new varieties are introduced, including miniature roses. In the early 1900s, Portland was known as the City of Roses for its 200 miles of rose-bordered streets. Also, check out Keller Fountain Park, Cathedral Park, and Washington Park, which houses the Oregon Zoo.
Reward your nature-filled soul with some great dining. Try Russian cuisine and sample from the extensive vodka list at Kachka—and end with a $1 glass of pickle juice. Pok Pok PDX on Division Street is the original site of Portland’s Pok Pok food empire, now expanded to four locations, started by a two-time James Beard winner who first encountered Thailand as a backpacker. Pok Pok PDX offers family-style dining from north and northeast Thailand. Saucebox, specializing in pan-Asian cuisine, boasts the best happy hour in Portland. Here, DJs provide a soundtrack to down signature drinks such as “Poolside with David Hasselhoff” and the “Kickboxer.” Snacks start at a mere $2. The farm-to-table Italian food at Clarklewis has appeared on several national lists. Indulge in tapas at Ataula or in the “pastry luncheonette” at Måurice, enjoy the 15th-floor vistas at pan-Asian Departure, and vie for a reservations-only table—one nightly seating only, Friday through Sunday—for the nine-course prix fixe at Holdfast Dining.
Close with sweets at Salt & Straw, where small-batch ice cream comes in flavors such as pear and blue cheese. Reconnect with your childhood breakfast at Voodoo Doughnut, where some confections are topped with Froot Loops or Tang.
No trip to Portland can be complete without browsing Powell’s City of Books, the world’s largest independent bookstore, housed in a former car dealership. This behemoth of literacy hosts more than 500 author events a year.
Coffeehouse and brewpub cultures are alive in Portland. For cafés, you’ll find charm and great java at Pip’s Original Doughnuts & Chai (if you are in town on your birthday, Pip’s will give you a dozen free doughnuts!); Spella Caffè with espresso made in the Italian style—and Italian desserts of gelato, sorbetto, and affogato; Egyptian coffeehouse Tov (in a double-decker bus, no less!); and family-owned Saint Simon Coffee Company, with a cold-brew flight. For brewpubs, try the dog-friendly Lucky Labrador; Hopworks Urban Brewery, which boasts a kid-friendly ambience; Culmination Brewing, with a vegan menu on Sundays; and Ecliptic Brewing, with its gigantic elliptical lighting fixture.
To enjoy this bike-friendly city, bring your own wheels or rent at Cycle Portland Bike Tours & Rentals, Everybody’s Bike Rentals & Tours, Pedal Bike Tours, or Kerr Bikes. Or join a bike tour and sightsee with others. The motto of BrewCycle Portland is “drink, pedal, repeat.” As you sit at a mobile bar, you help your group pedal from one brewpub to another. DW