City Guide: 24 Hours in Portland, OR


This is the first of several City Guide posts. I spent 4 years in Portland, OR and feel that I might be able to provide prospective visitors (such as yourself) with a rockin’ itinerary for a fan-freakin-tastic town!

Let me begin with a disclaimer….Portland is a wonderfully odd place. In fact, our catchphrase was “Keep Portland Weird.”

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Coming from the midwest at that time, I experienced a bit of a culture shock. But keeping my mind open and waking up everyday with the spirit of adventure, I morphed into somewhat of a Portlander myself, and loved EVERY minute of it.

So recap: Keep an open mind!


City Guide: 24 Hours in Portland, OR


  • How about a stroll? Check the weather ahead of time, most likely grab your favorite umbrella (if, that is, you want to be identified as a tourist) and head to my favorite district for a morning walking tour.
    • Alphabet District
      • Grab a coffee and go hipster-hunting at Coffeehouse Northwest
      • Walk up a few blocks to NW 23rd street and let your Portland Culture Feast begin!
        • Clothing shops such as Prana and Pop-up Shop will give you that classic homeless-chic that Portland is known for. You’ll have to grow your own beard, but the stores on 23rd can clothe you in suspenders, man-capris, and bowties until you’re blue in the face!
      • At this point, you might find yourself in need of sustenance, never fear….Kornblatt’s is here! It would not be an exageration to say that this little Jewish Deli is my favorite restaurant in Portland. Maybe it’s the carb-lover in me, or maybe it’s in the details of the place like giving you a BUCKET of pickles. Yes, you read that right…a BUCKET. Go get yourself a salt bagel and omelet. You won’t be disappointed.
      • Wander to the other stores that caught your fancy and maybe eat a chocolate or two at Moonstruck (I won’t tell anyone you had chocolate before noon!)



  • Alright my hungry friend, it’s time to go burn some calories so that you can eat more delicious, golden, Portland-y morsels.
    • Forest Park
      • Forest Park is one of the features of the city that I would brag about to all of my non-Portland friends. Why, you may ask? Miles and miles of every shade of green you could possibly imagine! Emerald, moss, mint; in Portland, it IS easy being green!
      • “But I’m not a hiker…..” Ummmm, but some lace-ups on and witness this gem. I promise, it is 100% worth it, and will show you a quintessential aspect of what makes Portland so dang special!
      • Stick to Wildwood trail if you want to see some beautiful forest scenery, and make sure to keep your ears open for mountain bikers. I’ve made a fool of myself on multiple occasions with a girl squeal of surprise!

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  • St John’s Bridge
    • On your way back to the city, take the St. John’s Bridge over to….you guessed it….St. John’s.
    • Wander down to Cathedral Park for a good look at another local hangout. The sea-foam colored bridge is beautiful and worth getting up close and personal with.


  • Not watching your waist? Good!
    • Take a seat at Montage. This eclectic dinner spot will have you sitting among the locals. Literally! It’s communal dining, and completely cool.
    • Get adventurous with the gator or frog legs…sorry Kermit!
    • Classic Portland means you must go to Voodoo Donuts. Personally? I’m not much of a fan. What can I say? I don’t like donuts. But that didn’t stop me from trying my hand at the Tex-Ass challenge. A dinner plate-sized glazed donut that you must eat in 80 seconds. Go on….fill yourself with regret, it’s part of the experience.
  • Hibernate at the mothership of all bookstores: Powell’s City of Books
    • You will get lost, it will be wonderful. Used books, new books, red books, blue books. Books about Portland, books about exotic plants, books about how to make contact with extra-terrestrial beings, you name it…they have it.

Nighty Night:

  • What’s a better send off into dream land than an adult beverage?
    • Portland City Grill is the place to be for a drink or 3.
      • Swanky? Check.
      • Good happy hour? Check.
      • 30th floor of the “big pink building?” Check.
      • Live piano music? Check.
      • Calamari? Check.

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I hope that this might guide you along the path of Portland-ness. Feel free to send questions my way, or suggest another itinerary. I feel like this is a great sampler of classic things to do in Portland, OR. Cheers!



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