48 Hours in Portland


Over the past weekend I ventured down to Portland for the first time and after hearing a variety of recommendations/opinions on the city from both colleagues and friend I really wasn’t sure what to expect. The main purpose of the trip was to cover the North West Music Fest, with my reviews coming soon in a separate post. The minute the opportunity came up I jumped on the phone to call one of my closest buds Jason to see if he wanted to tag along as my latest photog. Naturally, he was on board for a weekend road trip and the following is history.

Outside of the two nights covering the NWMF we knew there was a lot to see in Portland and it was fortunate that Jason had been to Portland before and one of blessed American friends, Morgan was readily available to cart us to all the hot spots. Let me start with this, holy shizah is Portland almost EXACTLY like Vancouver! The similarities are shocking in reference to the people, the attitude, the layout and vibe of the city. I love that everything was within 10 minutes walk/cab – definitely a perk when a person only has two days to see a city! Jason and I stayed at the ridiculously trendy Jupiter Hotel. From an outsider looking in, this hotel appears to be THE hot spot, but our experience wasn’t exactly stellar. The room was nice, for a converted/updated 1970s motor inn, but I am obsessive compulsive when it comes to bathrooms, and this is NOT a strength for the Jupiter. I’ll admit, the atmosphere was rad, the staff were excellent (especially Danny – the cute little gay boy who worked the graveyard shift), and the outside patio with an open fire to sit around was incredible post-bar. The location was perfect, on Burnside Avenue, we were a simple jaunt over the bridge to downtown (Random Insert: Portland has SIX bridges leading into their downtown core – SIX – it’s intense).

Something I discovered during our first shopping trip for mix and beverages was the Oregon has NO tax. The price on the tag is the price that you pay. Brilliant. Our proposed HST pales in comparison, but I digress. A lot of random fun was had throughout the day as we stumbled across a random ‘farmers market’ in the middle of downtown, ventured through weekend traffic (I can’t believe the US has traffic delays on the weekend) to a mall in the suburbs, and enjoyed roof-top cocktails avec Morgan at The Nines’ Hotel – Departure Restaurant and Bar. For anyone heading to Portland this is the spot to see and be seen. Complete with two GORGEOUS patios (one was closed for a wedding that we weren’t invited to – ridiculous), Departure showed us the gorgeous side of Portland. What really surprised me though was the lack of residential opportunities in the downtown core. Moving towards a similar Yaletown strategy to that of Vancouver, the Pearl district in Portland is up and coming but still about 5 – 8 years off. Definitely made for barren downtown streets, which is either a blessing or lame depending how you look at it!

The quote of the weekend came from our dear friend Morgan, as we regaled stories of boys and excitement and Morgan embraced his singleness, looking for a new opportunity possibly from North of the border. Being the gracious man that I am, I offered up my new roommate Kyle (aka. Dakota Fanning). Morgan’s sincere response:

Secretly, everyone wants a broken home.

M: “Can you bring a cute, nice Canadian boy to Seattle for me?”
D: “I can bring Dakota Fanning…”
M: “What the hell am I going to do with her? Act?! I need someone to F my A”.
D: “Eff my eh?”

I love a good random insert.

The HIGHLIGHT of the trip for me most definitely includes our post-bar rendezvous to 2nd Avenue/Street (hell I just made up the street number too), where this is an ENTIRE STREET dedicated to after bar feasts. In Canada we have limited options, with Vancouver’s being Pizza, Hotdogs, Poutine and Rice Bowls. In Portland however, you can have ANY FOOD FROM ANY WHERE IN THE WORLD. Literally. There were approximately 20 shanty-shacks set up serving Mexican, Thai, Greek and Indian. It. Was. Amazing. Naturally I went straight to the Mexican when I saw the opportunity to end my night with a chicken-taco-bowl. TO DIE FOR. Also, since the street is SO big it really is an excellent meeting place to connect with like-minded individuals who needed to break free from the club and grab a snack on the way home. There’s no shame in connecting over a $4 taco bowl, is there?

Overall, my experience in Portland was pretty great minus a few hiccups along the way. I tip my hat to Morgan for showing us an amazing 48-hours in the city and look forward to my next trip back.

Ps. The skate shops and brunch stops are some of the best in the world – reason enough to go to Portland!!

  • matintin

    We’ve stayed at the nines. Loved it.

  • Kyle D


  • Allan

    So – I made the mistake of reading this while in class. Poor choice when I laughed OUT LOUD – in the silence of the room – at this AMAZING quote, “M: “What the hell am I going to do with her? Act?! I need someone to F my A”.

    Enjoyable article Dan!

  • Dan

    Kyle – Calm down, you can’t use a nickname that’s already IN USE. I won’t be a copycat. You can do better…

  • Kyle D

    Dan I don’t think you would want me to use my original nickname. I have some class…

  • Dan

    Kyle – PUHLEASE!