Portland Travel Post: All the Fun and Sobering Facts You Should Know Before Going

My friends who have been to Portland before have been telling me for ages that I would love the city. So, when I landed a housesitting gig there I was thrilled! I would finally be able to live my best weird, vegan life (for three weeks)! To avoid burying the lead, I did enjoy my time in Portland, but akin to most of the cities I’ve traveled to, there were things I loved, things I didn’t like, and some “meh” moments in between. Let’s dive in, shall we?


Portland is White AF

Although Portland has a very progressive reputation, as the city tends to vote in favor of everything from gay marriage to legalizing marijuana, it is a very white city and intentionally so. Surprised? I was too. I knew that the population was overwhelming white before my visit, but I did not know the extent of Portland’s racist past and how it has greatly influenced the city’s socio-political landscape. Rather than delving into the very long and sordid tale of racism in Portland, I encourage you to read The Atlantic’s article that details the history. Context is everything.

With that said, I didn’t feel unsafe in the city or as though all eyes were on me as I explored. This was a stark contrast to my time in Boulder, which is also a very white town. I think the difference was that I actually saw POC more regularly throughout my time in Portland. Also, Portland is known to be pretty accepting of all things atypical, so walking around with lower-back length Marley twists and a septum piercing had me feeling like a cliché.


The Ideal Housesitting Situation

Meet Oz, the kitty I sat for while in Portland.

As I mentioned earlier, I came to Portland after booking a housesitting gig that was set just outside of downtown Portland, and required me to look after a one-year old cat. Things went well. My host had fully taken advantage of the Pacific Northwest climate and had a huge, gorgeous garden in her backyard. Outside of the usual flowers and trees, my host also grew a bunch of veggies and fruit, which meant that I got to eat fresh produce without having to pay or it. (Be still my beating heart.)


The Lowdown

I know you’re thinking, “Okay, that’s cute, but what is there to do, see, and eat in Portland?!” The answer is: a lot. Listed below are some highlights.


Where to Eat

I’m vegan, so take or leave the following information:

  • Ichiza Kitchen. This was a pan-Asian spot I went to that was pretty much a hole in the wall with some tables, chairs, and a makeshift kitchen thrown in. With that said, the food was absolutely delicious and the service was equally as great.

    ichiza kitchen-portland food scene-vegan
    My lunch at Ichiza Kitchen.
  • Los Gorditos. The name of this place is apt. The portions are huge, the food is delicious, and they offer separate menus for both vegans and omnivores.
  • Virtuous Pie. A cute little vegan pizza spot that also offers vegan ice cream. The restaurant is housed in part of a repurposed warehouse, which is cool. I ate here with a friend who’s an omnivore and we both enjoyed our meals.
voodoo doughnuts-portland food scene-vegan
The most delicious doughnut ever.
  • Voodoo Doughnuts. I’m going to be honest and say that I went here because I felt like I had to given how popular this spot has become. However, I have to remain honest and say that I really thought I was going to be disappointed, but I wasn’t! I’m not a big of doughnuts (or most sweets for that matter), but I thoroughly enjoyed the vegan frosted Oreo doughnut I got here.
  • Deadstock Coffee. Portland is known for its coffee scene and places like Stumptown Coffee Roasters have become cornerstones. However, I’d like to shift your attention to Deadstock Coffee, which is a black-owned coffee shop that also sells apparel. The place has no menu, which forces you to actually engage with the person selling you your cup of Joe (which in my case was the owner himself). The coffee is delicious and while the décor leaves something to be desired, the “local spot” ambience makes up for it.


Places to Go

  • Powell’s City of Books. This place is equal parts overwhelming and incredible. Powell’s is the largest chain of independently owned bookstores in the world, and the Powell’s in downtown Portland has 1.6 acres of retail space. That’s insane. While I didn’t get to spend nearly as much time as I would like to in the store (I need to live in that store for at least a full year to be honest), I did pick up a few used books that were in great condition for a good price.

    pittock mansion-portland-pdx
    The view of the entrance into the Pittock Mansion.
  • Mill Ends Park. The world’s smallest park is definitely worth a visit. The history of how the park came to be is just as adorable as the park itself.
  • The Grotto. One of the most beautiful places I went to while visiting Portland, The Grotto is a Catholic shrine dedicated to Mary. However, the shrine is accompanied by 62 acres of very green and serene gardens.
  • Pittock Mansion. I debated putting this one on the list because while the mansion is pretty and gives you great views of downtown Portland and Mount Hood, the museum itself is pretty underwhelming. I suggest visiting on a nice day and going for a hike around the property’s many public trails, as well as wandering through the gardens on the mansion grounds.



Things to Do

  • See a movie in a Living Room Theater. It started raining during one of my trips into downtown Portland, so I opted to see a movie. This theater is right up my alley. There’s no kids allowed after 7pm, you can order dinner and drinks before heading into your showing, and the theaters themselves are small rooms complete with Laz-E-Boy-style furniture.
  • Look at some dope street art. There’s street art everywhere in the city. Look at it, take pictures, and support local non-profits that are working to increase public access to art.


Where to Work

Since I’m a digital nomad, my trip to Portland wasn’t a vacation. Since I was working during my time there, I was on the hunt for a good place outside of my housesitting spot to hunker down and get stuff done. Listed below are a couple of places I scoped out.

deadstock coffee-cafe-portland-pdx
This is what greets you get before heading into Deadstock Coffee. I’m in complete agreement.
  • Stumptown Coffee Roasters at the Ace Hotel. I read somewhere online that this was a good place to get work done. Whoever wrote that lied. The café is small and attached to the lobby of the Ace Hotel, which meant that I was sipping on my overpriced latte while sitting on the lobby couch balancing my MacBook on my thighs.
  • Urban Grind Coffee House. This place is ideal for those who plan on delving deep into a project and need to remain caffeinated. The space has ample seating and it’s usually pretty empty. The only downside is that the wifi code changes every couple of hours, so if you plan to be there for awhile you have to go back up to the cashier to get the new code.





As I mentioned in my epic post about housesitting, since I only take housesitting jobs that are at least 2-3 weeks in duration, living close to amenities or close to public transportation so that I can get to said amenities is a necessity. I’m way too broke to pay for a rental car for multiple weeks and Portland is a city connected by bridges, so having access to different modes of transportation aside from a bike and my feet was a must.

It’s also important to note that Portland’s population is growing and the city’s infrastructure has not caught up in a few ways. One example is that the highways are fairly still small, which means there always seems to be traffic no matter what time of day it is. With that said, listed below is a more detailed review of the various modes of transportation I used during my stay.

  • TriMet. During my time in Portland, I lived within walking distance to a bus stop that went through downtown, which was great. The cost of using any part of the TriMet system was super cheap, as the city charges per ride ($2.50) and once you reach two rides ($5.00) your voucher is good for the rest of the day. Also, my bus ran every half hour, which was pretty good considering that I was in the suburbs. I also used the MAX Light Rail (similar to a tram or above-ground subway) while in Portland proper, and found that the train ran frequently.
  • Uber. Ubering into the city was crazy expensive since I couldn’t get UberPool where I was staying, so I didn’t use it at all while I was there. (Note: UberPool does exist in Portland, but only in certain areas.)
  • Biking. I didn’t use a bike, but noted a fair amount of bikers and bike lanes. Also, the city is pretty flat, so unless you’re crossing a bridge to get from East Portland to West Portland or vice-versa, you should be good.
  • Walking. The city is very walkable. I would usually take the bus to a central location and explore on foot from there.


Final Thoughts

All in all, I find Portland to be a quirky, charming little city. Even though it’s the largest city in Oregon, it is still relatively small as cities go and the vibe is, subsequently, pretty relaxed. I also loved how affordable it was for travelers like myself. The no sales tax really was the cherry on top of my budget sundae.

Have you been to Portland? Are you a Portland native? If so, what other recommendations or advice do you have for digital nomads?


4 thoughts on “Portland Travel Post: All the Fun and Sobering Facts You Should Know Before Going

  1. I loved Portland! Some of the buildings seem to be of the future and the than the rest were old – there was like no in between 😂😂


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