How to Do the Hipster's Tour of Portland, Oregon

Nouvelle log cabin living at the Doug Fir Lounge

Portland, Oregon, is the small town that thinks it's a city. Portland is clean, green and a snap to navigate, either by foot, public transportation or car. For such a small place, it manages to pack a lot of art, nightlife and hipster fun. There are tons of independent businesses with their unique flavors. A hipster's tour of Portland can include boutique shopping, club-hopping, killer cocktails, even better desserts, indie cinema and art happenings.

Things You'll Need

• Jeans
• Umbrella

Instructions

1. Pack smart. Except for the summer months which, in Portland, are July and August and maybe a little bit of September, plan for rain. Bring layers and good walking shoes. Be advised that, for whatever reason, many Portlanders wouldn't be caught dead carrying an umbrella. Perhaps because doing so would identify them as ex-Californians? An awning or one of Portland's 3 billion trees should provide enough shelter for a brief shower, or sneak into a cafe or brew pub to wait out a longer drenching.

2. Hit the Pearl District. This is the first stop of many travelers. The one-time industrial area has given itself over to lofts, high-end galleries, microbreweries and of-the-moment restaurants. Powell’s City of Books (1005 W. Burnside), the world’s largest independent bookseller, anchors the neighborhood. When Powell’s overload hits, follow the scent of organic coffee, fresh-brewed at Pearl Bakery (102 NW Ninth Avenue), accompanied by the artisan bakery’s chocolate bouchons.

3. Go shopping. The Pearl’s caffeine and sugar rush should generate energy for shopping. Fortunately, Northwest 23rd Avenue—known as “trendy-third”—is nearby. TWIST (30 NW 23rd) sits at the top of the tree-lined thoroughfare, beckoning shoppers with art jewelry. Stop in at decadent Blush Beauty Bar (513 NW 23rd) to scoop up some NARS Orgasm gloss and indulge in a Flirtini, a 10-minute touch-up. Browse the finds at The Bee and Thistle (2328 NW Westover Road), lines adorned with lace, beads, appliqués, geisha images and crocheted handiwork. Next up is Dazzle (704 NW 23rd). If it glitters, it’s sold here. Chunky watches, handmade shoes and flashy clothing get the star treatment. Don't forget to make your pilgrimage to Saint Cupcake (407 NW 17th), the retro chic repository of the gourmet treat.

4. Go offbeat. Portland excels in the alternative. Nightspot VooDoo Doughnut (22 SW Third Avenue) fits the bill, famed for its voodoo doll-shaped confection as well as its performance art, Swahili lessons and weddings. Pop by Ground Kontrol (511 NW Couch) to try your hand at old-skool Atari video games. Other less-traveled attractions can be found on Portland’s east side. In the bohemian Hawthorne District, stop by the Bagdad Theatre and Pub (3702 SE Hawthorne Boulevard) for a brew and a movie, or venture northeast to the diverse and vibrant Alberta Arts district, home to ethnic restaurants, punky galleries and café culture.

5. Sleep in hip quarters. Portland's stylish Jupiter Hotel (800 E. Burnside) awaits you. The chic and funky hotel sits next to Portland's favorite log-cabin-gone-hipster-lounge, The Doug Fir. Live music and stiff drinks are the main attractions. Across the street is a happening little strip of galleries and shops that host the First Friday art walk. The highlights are the Grass Hut Gallery, featuring pop surrealism and lowbrow art by Bwana Spoons, APAK, Tim Biskup, Scrappers and others, and Moshi Moshi, a favorite spot to find Japanese collectible toys.

Tips & Warnings

• The consistent favorite for coffee is Stumptown.

• It's against the law to pump your own gas in Oregon.