West Coast Trip 2015 – Portland

Portland skyline and Willamette River

Next stop on #WCT2015 was Portland, Oregon.  After an early morning Einstein bagel (chocolate chip with plain shmear, not toasted, duh), the four of us who remained headed over to the Amtrak station in the International District of Seattle, and hopped on a train headed south.


  • Breweries
  • Food trucks
  • Strip club – Portland is apparently the strip club capital of America, gotta do it…
  • Weirdness

DAY 4 – Monday

The train from Seattle to Portland took about 4 hours, and it was a picturesque ride.  The weather was gray and dreary, but I imagine the scenery would be quite beautiful under the right circumstances.  At only $35 a ticket, I highly recommend the train for anyone going from Seattle to Portland.

We arrived around 1:30pm, and we knew that we had to get right down to business, since we really only had a day and a half to get weird in Portland.  We called an Uber, and headed to our Airbnb in Ladd’s Addition neighborhood in SE Portland.  The Airbnb was quite nice – a little carriage house to ourselves in somebody’s backyard.  And bikes available to borrow, as you’d expect in Portland.

After a brief rest, we headed out to some breweries!  First up was Cascade Brewing Barrel House, known for their sours – a great spot for an adventurous beer drinker.  It was walk-able from the Airbnb, so we decided to walk it out to take in some sights and sounds.  The stereotypes that I had heard about Portland seemed to be true so far: some weirdness, lots of breweries, tons of bikes, some hippies, some homeless, and signs of gentrification.

After Cascade, the original plan was to head to Rogue, which sells brews back in Rochester, to check out their brewery.  We took an Uber to NW Portland, but when we got to Rogue the Uber driver recommended that we get some food at another brewery right across the street.  We were getting pretty hungry at this point, so we headed into 10 Barrel Brewing.  We filled up on fantastic pizzas, and also got some tips from our waiter, who incidentally had recently moved from San Francisco.  He gave us some great recommendations for the next leg of our trip – by now I’ve forgotten the name, but thanks waiter guy!

Next, we stumbled across the street to Rogue, which actually has a couple of locations in Portland.  This one was a dark, kind of divey bar with board games and a wide selection of their brews.  I got one of my probably top 10-20 beers of all time, the Hazelnut Brown Nectar.  The ladies got flights, and we played some games to close out the night.

DAY 5 – Tuesday

Rachel and I woke up early for a run around town, down SE Hawthorne to the Eastbank Esplanade.

a food truck pod in Portland
Pod spotted on the morning run got me real excited for our upcoming food truck dinner…

About 4 miles and a few photos later, we were back at the ranch and rounding up the rest of the troops for breakfast.  We chose Pine State Biscuits, and we were not disappointed.  All reports said that we would encounter a line, but we were luckily able to walk right in!  If you’re looking to avoid the wait, I guess Tuesday morning is a good time to go.

After breakfast, it was time for…breakfast dessert?  The tourist in all of us came out a little bit, and our next stop was Voodoo Doughnuts.  We weren’t able to finish the whole box, but there were plenty of homeless folks outside who were happy to take the extras.

a box of Voodoo Doughnuts
Voodoo Doughnuts – with some sexual innuendo names that I don’t remember…

After Voodoo, we took an Uber to Powell’s City of Books in the Pearl District, the iconic bookstore with the claim to fame of being the largest independent bookstore in the world.  I don’t have hard data to back that up, but I can say that it is pretty damn large.  Floors on floors on floors of books, new and used, to get lost in for hours.  We did spend a good hour and a half there, and did not come close to checking out the whole store.  If visiting Portland on a rainy day, Powell’s should definitely be on the to-do list.

Next up were a couple more touristy activities: the International Rose Test Garden, and Pittock Mansion.

view of the Portland skyline from Pittock Mansion
Portland from Pittock Mansion – a little too cloudy to see Mt. Hood 😕

The two are located very close to each other, a short ride outside of downtown to the west.  Both are great for photo ops.  Typically the Pittock Mansion type of activity is not for me, but I did enjoy this one.  The view of Portland and Mt. Hood from the backyard alone was worth the price of admission (which was only $10).

After the mansion and a quick trip back to home base to change, we headed back out for an early food truck supper.  We headed to the NE quadrant for to Guero PDX at Pod 28, which was a quaint little pod with about 5 or 6 food trucks, and a bar truck.

I’m a sucker for good street food, and this was fantastic.  I wanted a 2nd, but the ladies correctly pointed out that there was more work to be done!  Namely, a flight at Migration Brewing, a couple beers and some appetizers at Burnside Brewing (“Sweet Heat” is a must!), and second supper (sushi) at Mirakutei.

Finally, we were feeling good and liquored up enough to hit the strip club.  The experience of strolling into an empty strip club in what felt like a fairly residential area, at 11pm on a Tuesday night, with three girls in my crew was something I will never forget.  All I will say is fun times were had, and we had a hard time pulling Hilary away from the ATM…

And that was it for the Portland leg of the trip.  It’s a shame that we had such a short amount of time there, and I would definitely like to go back soon to explore further.  My main takeaway from Portland was that it felt like perhaps the most livable city that we visited on this trip.  We were sad to leave the next morning, but pumped for San Francisco!


  • Food trucks
  • Burnside Brewing
  • Overall vibe of the city

Next Time:

What is your favorite place to get weird in Portland?  Hit me up in the comments!


2 thoughts on “West Coast Trip 2015 – Portland

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