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Trip List by Guzzle

Three Perfect Days in Portland, Oregon

Apr 3, 2006  A part time Portlander
3.5 of 5 bubbles based on 5 votes

A great way to spend three days in Portland - the best restaurants, bars and sights.

  • Explore locations featured in this Trip List: Portland
  • Category: Perfect weekend
  • Appeals to: Couples/romantics, Honeymooners, Large groups, Students, Budget travelers, Tourists
  • Seasons: Winter, Spring, Summer, Fall
  • 1. Wake up at The Jupiter
    Jupiter Hotel, Portland, Oregon

    Admire the retro furnishings of this funky renovated Southeast Portland gem. Hang with the hipsters in the lounge before heading out to discover the city.

  • 2. Find out how good Oregon tastes.
    Portland Farmers Market, Portland, Oregon

    Wander through the wares at this popular farmer's market.

  • 3. Get some reading material
    Powell's City of Books, Portland, Oregon

    If you’re more in the market for a book on food, browse the shelves of the world’s (alleged) largest bookstore, Powell’s.

  • 4. Bluehour
    Bluehour, Portland, Oregon

    In the gallery and loft-saturated Pearl District, a pleasant stroll from Powell’s, the stylish, high ceiling-ed Bluehour, provides great takes on American cuisine. Mouthwatering steak frites star.

  • 5. Strol round the Japanese gardens

    Work off those fries, walking up to the top of the Japanese Gardens. Peace prevails and the views of Mount Hood are magnificent.

  • 6. Try Thai food fit for Kings at Typhoon

    The addictive Typhoon delivers sumptuous Thai food, from peasant plates to food fit for kings.

  • 7. Brucnh at Besaw's
    Besaw's, Portland, Oregon

    Line up with the horde of eager Northwest Portland residents who crowd this intimate café. Scrambles, waffles and Bloody Mary's are the attraction here!

  • 8. Explore the Hawthorne neighborhood
    Bagdad Theatre, Portland, Oregon

    Head back across one of PDX’s many bridges, to the Hawthorne district. Shop for funky homewares, eclectic outfits, cutting edge CDs, or catch a second-run movie at the Arabic-styled Bagdad Theatre. Choose from popcorn or beer and pizza at this McMenamins’ cinema pub.

  • 9. Munch on Mexican delights
    Esparza's Tex Mex Cafe, Portland, Oregon

    Feast amid the tack and kitsch of Esparza’s – home of Mexican-hued mayhem, a tequila shrine, a zoo’s-worth of stuffed creatures hanging from the ceiling and vast portions.

  • 10. Catch a show
    Jupiter Hotel, Portland, Oregon

    Back at the Jupiter, make your way downstairs to the Doug Fir lounge and catch an up and coming band or an alternative name from out of town, in one of the city’s top live music and club venues.

  • 11. Go back to school
    McMenamins Kennedy School, Portland, Oregon

    Whether you've got young ones with you, or are just young at heart, head back to school at the Kennedy School - where bars and a tasty snack menu have replaced the school canteen food, and second-run movies show in the old school hall. Although the building has been renovated, you still expect frowning nuns to appear round the corner any minute!

  • 12. Mojito time

    Head for the industrial chic of Holocene on Morrison for the best mojitos in town. Different clubs and afternoon events attract a hip and eclectic set. Once a month Tart fills the floor with hipster dykes, and Double Down attracts a mixed gay/lesbian set. But any visit is sure to showcase a bohemian cross section of this laid back city's finest.

  • 13. For more beats… and some Vietnamese treats too
    Green Papaya, Portland, Oregon

    This unassuming spot is a delicious surprise. Whether you sit in the main restaurant (Morrison door) or round the corner in the funky bar section, food is absolutely sumptuous. Happy hours feature many early evenings and from 9-midnight Thursday through Saturday. A hip set of 20-somethings nibble on $2 appetizers and take advantage of appealing drinks promotions, as an enthusiastic DJ spins an up set of house, pop, retro and funk. A perfect later night stop - where there always seems to be a table free.