Portland, Oregon

Portland is perhaps best known for its excessively rainy weather, its acclaimed urban planning, and coffee. If you couple these distinctions with the city’s lesser known characteristics—a gorgeous natural setting, a thriving arts and food scene, and a notably progressive political climate (former president George H. W. Bush once referred to it as “Little Beirut”)—then you’re mixing up one interesting cocktail.

Portland is nothing if not eclectic, and its happy blend of mismatched communities, among them artists, bicyclists, and drag kings, is a testament to its livability.  The best time to visit is between May and October, when the sun is out and Portland flavor is at its peak.

A Great Portland Day

Portland is situated in the Pacific Northwest, a region known for its standout coffee selection and café culture. When in town, get your coffee from the best: Portland’s ultra-hip Stumptown. If you’re visiting on the weekend, grab your cup-o-joe and stroll up to the Portland Farmers’ Market. Enjoy a breakfast burrito, listen to live music, and purchase some local foods for later in your trip.

From the market, it’s a short walk to what may be Portland’s main attraction: Powell’s City of Books. Powell’s is wonderfully large (use the store maps to assist you in getting around), and if books are your thing, you may want to allot a couple of hours here to fully appreciate its enormous collection of rare, used, and discounted materials. For further reading, walk one block south to Reading Frenzy, a petite, equally cool book shop well-stocked with small press books and local ’zines. Afterwards, hit up Jackpot Records, one of the city’s much-loved independent record stores.

If browsing makes you hungry, head to Half & Half, a teeny and tasty sandwich shop offering rotating sandwich compilations (the peanut butter and marshmallow panini is a retro dream). Like most Portland establishments, Half & Half prides itself on its well-crafted espresso drinks. Find yourself a seat at the window and enjoy a quintessential Portland activity: reading a book while sipping local coffee.

To experience the Oregon wilderness, spend an afternoon in Forest Park. It’s the nation’s largest public park, with 5,000 acres of seemingly endless shades of green. Miles of trails wind peacefully along a scenic ridge that overlooks the Willamette River. Other outdoor options include the International Rose Test Garden and the adjacent Japanese Gardens. During peak season at the Rose Garden (May – September), 7,000 rose bushes are in bloom. The Japanese Gardens feature a stone and sand garden as well as cool woodland trails and reflecting pools.

If shopping is your form of exercise, pay a visit to upscale NW 23rd Avenue, where you’ll find the city’s most elite retail clothing stores. Try Seaplane for chic, deconstructed-yet-playful pieces—the person behind the counter is often the woman who designed the clothing.

You’ve hit the hipster wardrobe jackpot in Portland. There’s no shortage of vintage clothing stores, the best of which are in Southeast Portland. The Red Light spans a city block and has all the belts, heels, pink tutus, and vintage T-shirts you could want for a hip ensemble. An added bonus is the in-store photo booth, where you and your friends can document your transformation from a fashionable “before” into a super-stylish “after.”  Local insiders shop at Xtabay, long-loved for its superb vintage wares and a miraculous sales staff who effortlessly direct you to the perfect party dress.

Portland has incredible dinner options. If it’s early and you’re feeling social, hit the Portland City Grill for happy hour. Its prime location on the 30th floor of the “Big Pink” building offers gorgeous city views. Order a “pink moment” martini and enjoy the five-star food at fast food prices.

Portlanders love to party, and clubs are as diverse as the people hitting the town. Downtown, try Berbati’s Pan for the latest in indie rock, then grab a bacon-maple bar or other deep-fried delight from the legendary Voodoo Doughnut. Or, rally your friends for ’80s night at The Fez with DJ Gregarious, a Portland mainstay. If you’re feeling more low-key, try the Laurelhurst Theater, a vintage movie theater that serves up retro films, local microbrews, and pizza. If you’re feeling more off-key, head two blocks down to Chopsticks Express, long the blissful karaoke haunt.