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Portland, Oregon: My Greatest City in America?

Why didn’t anyone tell us that there are so many incredible cities in the good ole USA… we could have saved a lot of money on international flights if we just would have toured within the continent for the past 15 months.

Okay, we probably still would have explored another country or two, but really… we have nothing, absolutely nothing, to complain about throughout our time in the States. We loved our one night in NYC, the beaches in Fort Lauderdale are some of the finest on the planet, Santa Monica was the perfect place to tour with Mom (and of course to see Jeopardy!), and between cycling the Golden Gate bridge and drinking Napa Valley wine, we thought we would may never leave San Fransisco….

Portland, Oregon

…and then there was Portland, Oregon.

Oh how I wish the weird, chilled-out city of Portland (aka Portlandia) would hire me so that we can live in your fine city forever. I am serious. If Portland was a woman, Shawna might have some competition.

Okay, maybe that’s going overboard. I would never love a city more than my wife….

(well, unless that city was Portland.)

So what is it? What the hell makes Portland, Oregon the greatest city in America according to the testicular half of Get Up And Globe??!

We actually arrived in Portland, after taking the overnight train from San Francisco. It was around an 18 hour rail ride, but I am a huge fan of train travel, so this actually went by quite quickly.

Upon arriving we headed out Union Station, jumped on the local tram system, and easily navigated ourselves towards the home of Keith and Angela, our incredibly kick ass Couchsurfing hosts for the next three days. There was such an interesting 1990s vibe to this place… I was immediately hooked.

Shawna and I with CSing hosts Keith and Angela! Hangin at a food cart pod!

If you know of Portland (and I can emphatically report that not enough people do), you know it is famous for many things, and by the end of our time there, with the help of Keith and Angela, I think we had stumbled onto most of them:


Ahhh yes, we are off to a great start, eh? There are so many incredible microbreweries and pubs in Portland, it is nearly impossible to comprehend. Apparently the city ranks 5th in bars/taverns/pubs per capita in the entire country. Thanks to the locally famous McMenamin brothers, they even have an old elementary school and funeral home which they have converted into pubs! From the Alaskan Smoked Porter to Upright’s Supercool IPA, you will never leave Portland thirsty!

Food Trucks

After all the brew, you will eventually get hungry, and with over 500 food trucks/food carts scattered through Portland, you will definitely find something yummy for your tummy. Ethnic food, burgers and fries, desserts, soups, and vegetarian and vegan food carts can be found gathered together on food cart pods. As a sidenote, when Shawna and I were first looking for a Couchsurfing host, nearly every profile we looked at stated that they were vegan. Although we are completely cool with this, rest assured that you can still get a great beef/bison burger in this city if you are carnivorously inclined.

Shawna’s favourite Food Truck

*sigh*, just another sausage party…

Pedal Power

The most bike friendly city in the United States? Undoubtedly! The city is planning to spend a whoppin’ $613 Million on cycling infrastructure in the next 20 years. The goal is to have nearly 1,000 miles of bike paths throughout the city. It’s incredible! Right now 300 miles already exist in the city which make it feel like every street was built wide enough to accommodate a proper bike lane. This was a fun place to pedal!

Portland is so bike-crazy, that they have even organized an annual Naked Cycle, where thousands of participants strip down and gear up for the 12 mile ride through the city.

Street Fairs

Angela and Keith took us to the Belmont Street Fair, which was one of the last festivals/fairs of the season. Live music, great eats, tons to see… and best of all, entry was free!!

Shawna and I limbering up at the Belmont Street Fair

Nice music, but this guy was not the headliner

Green Space

If you Google the city of Portland, and then zoom out a little, you will see a whole pile of green. If you are a hiker, or a nature-lover of any type, you will love the state parks, mountains, and waterfalls which are essentially in your backyard! While we were in town, we took a beautiful but not-too-tough hike up around Multnomah Falls in Colombia River Gorge, capped off with, of course, a fine Portland lager!

Keith, Shawna, and I

Powell’s City of Books

Back in Regina, Shawna and I love nothing more than spending a few hours roaming through our Chapter’s bookstore with a hot coffee on a Saturday afternoon. Well, comparing Chapter’s to Powell’s is like comparing a hot dog to beef tenderloin. I could have camped out in this bookstore (which occupies an entire city block!) for weeks! If you have any appreciation for reading, get your literate ass to Powell’s the next time you are in Portland. And yes, they have a coffee shop attached to, so you don’t even need to leave the building for meals.

Photo courtesy of

Voodoo Doughnut

Okay, let’s get this straight… I really don’t even like doughnuts. Okay, no that’s not true… I do like doughnuts…alot! But because I generally like to participate in actions which keep my arteries unclogged, I rarely indulge these days. But if I actually did live in Portland, I fear that my stops to Voodoo Doughnuts would become a daily (at least) event! It was late afternoon on a quiet Sunday when Shawna and I found our way to this landmark, and there was a lineup around the corner to get into this place!?!? Try their Bacon Maple Bar (yes, with real bacon!), the Captain My Captain (vanilla frosting and Cap’n Crunch), the Memphis Mafia (banana chunks, cinnamon sugar, chocolate frosting, peanut butter, and peanuts), or even the tripod shaped, Bavarian cream-filled doughnut aptly named… Cock n Balls (rest assured this doughnut was left unsampled). The best news is Voodoo is only a few blocks away from Powell’s, so hitting both of these must-sees in the same afternoon is easy as pie.

The lineup

A nice light lunch!

You know it’s good if Shawna won’t share!

One hundred thank you’s go out to our awesome Couchsurfing hosts, Angela and Keith. There is no way we would have had the outstanding experiences that we did without them.

Oh they look crazy, but they mean well… :)

So, have we convinced you to get your butt to Portland yet? Can you name us a cooler city than Portland in the US? Let us know, we would love to hear from you!


Also, if you are interested be sure to check out Get Up and Globe’s latest string of interviews. Upon returning home, we admit we have really been quite spoiled. We have taken in every second of our fifteen minutes of fame… with interviews on blogs, on TV, radio, and in local magazines we definitely felt like celebrities! You can find them all here!!

Amen Brother!

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9 Responses to “Portland, Oregon: My Greatest City in America?”

  1. Sofie November 20, 2012 at 12:30 pm #

    Looks like you guys had an amazing time!
    I must admit that I’d never thought of Portland as a trip destinations, so thanks for bringing it to my attention!
    Sofie recently posted..Girls weekend in Paris: our itinerary

    • Skott November 23, 2012 at 8:29 pm #

      I couldn’t recommend the city enough Sofie – get there whenever you can… you won’t regret it! Thanks for reading!

  2. Kim November 23, 2012 at 12:38 am #

    Awww, it makes me miss home! Glad you had a good time in fantastic Portland.
    Kim recently posted..Six months on the road and thoughts on homesickness

    • Skott November 23, 2012 at 8:30 pm #

      Well, the good part is… home will still be here when you come back from your amazing adventure! But yes, you are very fortunate to have such a ridiculously city to call home…. Travel safe, Kim.

  3. Izy Berry - The Wrong Way Home December 2, 2012 at 11:05 pm #

    I didn’t know much about Portland. I knew that Free Willy was filmed in Portland, right?
    Izy Berry – The Wrong Way Home recently posted..Chiang Mai

    • Shawna December 9, 2012 at 5:00 pm #

      We have to take your word on that one Izy…. but Willy or no Willy – Portland is the place to be! :)

  4. Jennifer Burton January 23, 2013 at 4:08 am #

    I nominated you for a blog award:
    Jennifer Burton recently posted..Liebster Award

    • Skott and Shawna January 23, 2013 at 5:18 am #

      You did what??!! Jenn, you are amazing! Thank you very much… that is crazy humbling…woo hoo!!!! :)

  5. Spencer May 10, 2013 at 7:56 am #

    I loved Portland! Not least because it took me to MT Hood. I also loved the food there and the people were pretty friendly too.
    Spencer recently posted..Where To Stay During The Ashes Series

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