Paul and Annie’s Stumptown Recount!

Reflections from living in Portland, OR for a month

Annie L. Lin
19 min readAug 20, 2023

In July 2023, Paul and I embarked on something we had been interested in doing for a while. We moved out of our house in the San Francisco Bay Area, and began a nomadic adventure of living for about a month each in a variety of cities, in search of a place to call home. In case you’re curious why we would make such an insane decision, the full context is here.

Stop Number One on our itinerary was Portland, Oregon. A city of twelve bridges and a thousand nicknames (Stumptown, Bridgetown, Rose City, Rip City, Portlandia, PDX… the list goes on), Portland was always going to be on the list. I had been there four times prior. Paul had been there twice before. And every one of those trips had been magical. We loved the food, the coffee, the beer, the nature, the quirkiness. But none of those prior visits had been for more than a few days at a time. We were giddy and curious to find out what it would be like to live in Silicon Forest for a whole month. (Okay, can we please petition for Portland to never be called Silicon Forest?)

4th of July in Portland — the city shut down Morrison Bridge to car traffic so that pedestrians could watch the fireworks from the bridge

Fast forward a month, and, well, all we can say is that as City #1 on our grand adventures, Portland sure set a high bar. A very, very high bar. On our drive out of Oregon toward Colorado, Paul and I spent an hour recording our reflections of PDX. To structure the conversation, we each wrote a few questions ahead of time. We had shared the questions (but not any answers) with one another, so that we had some time to think about them. We then asked each other those questions during our long drive, and both of us responded to all the questions live. The only exception to this was the one at the end about our favorite restaurants — we came up with that Power Five list together.

We recorded our entire long, meandering conversation. I then took the transcript and edited it into this post. The questions that made the cut below are:

  • Describe Portland in three adjectives. Why those adjectives?
  • If Portland was a dog, what breed would it be and what would its name be?
  • You have $50 to spend in a day in Portland. How would you spend it?
  • If an asteroid was coming to hit Portland, what quadrant of the city would you save?
  • If you could wave a magic wand and change one thing about Portland, what would it be?
  • What was your impression of the rest of Oregon (outside Portland)?
  • Our five favorite restaurants in Portland!
Biking very quickly became our default mode of transportation while we were in Portland

Q1: Describe Portland in three adjectives. Why those adjectives?

Paul: I was deciding between a few different ones, but in the moment, I’m gonna go with: quirky, hedonistic, and marketable.

I think quirky is fairly straightforward. Portland’s motto is basically “Keep Portland Weird.” There’s all kinds of interesting mashups of cuisine and retail, like a half brewery half running shop (shoutout to Run Pub). There’s just a peculiar-ness specific to Portland and the Pacific Northwest that they’ve really embraced, that I find very endearing.

This piano exists in the middle of a random parking lot by Cathedral Park. Por qué no? (which we are convinced should be the official slogan of Portland)

And hedonistic: Portland is definitely a city that I feel like embraces the feeling-good parts of life. Like, lots of breweries, amazing beer, lots of amazingly delicious food that’s really fresh. And apparently more strip clubs per capita than any other city in the whole country. It’s a a city that I think just really likes to have a good time.

Finally, marketable — I think maybe in two different kinds of ways. One is a very positive framing where it’s just so easy to, like, take a good picture or something in Portland. It’s so easy to find a beautiful spot along the Willamette river, and to just look out and be like, man, this is a beautiful city, particularly in the summer. Then there’s the “marketing” part of “marketable.” Portland’s marketing video did a amazing job selling the dream of Portland. All of those things put together, makes it very easy to grasp what Portland’s essences is.

This is hands-down the best marketing video for a city that we’ve seen (and we’ve been watching a LOT of city marketing videos). Paul and I both teared up re-watching this recently.

Annie: I think my three adjectives have a lot of spiritual overlap with yours, even if they’re not the same words. Mine are: playful, artisanal, and bon vivant (that’s an adjective, right?).

Playful is probably my number one adjective for the city. I just feel like Portland has such a sense of humor and doesn’t take anything too seriously. There were times in Portland when it kind of felt like we were in the middle of a giant inside joke, that the whole city including the government of Portland is in on. Lots of restaurants and commercial establishments like to have fun with their menus, etc. I think you also see the playfulness come through in the really, really creative food. You touched on this too with Run Pub. That’s just one example of so many where the city is just like, “let’s have some fun with this.”

Bathroom sign inside Ecliptic Brewing, in the Mississippi Ave part of town

The second adjective, artisanal, has some overlap with that. I think it’s a city that doesn’t necessarily like traditional ways of doing things. They like craft, they like local, and they really care about those things.

And bon vivant… is a lot of what you said too. Every time I’ve been to Portland, it just feels like this is a city that really likes to live a good life. From the amazing amount of food, to the amazing amount of coffee, to the amazing amount of beer and cocktails. Just everything everywhere all at once. It really feels like people here know how to live a good life. Honestly it’s really cool perspective to have, every time I come here.

Reverend Nat’s Hard Cider, on Division St (SE)

Q2: If Portland was a dog, what breed would it be and what would its name be?

Annie: So I have to be honest that I don’t know a ton about dog breeds. But I ended up picking the Australian Shepherd. I think Australian Shepherds are known for being really playful. They’re also big and fluffy and there’s something about that that feels very playful also. And they’re dogs that love the outdoors, similar to Portland and Oregon which just feel like a place where there’s so much gorgeous nature, and people are really big fans of outdoor activities.

In terms of the name, I think I’m gonna have to go with Douglas Fur. The “Fur” part obviously is spelled F-U-R (not F-I-R). For those who don’t know. the Douglas fir tree is pretty much the official tree of the state of Oregon. If you look at Oregon license plates, there’s actually a Douglas fir in the middle. There is also an unofficial flag that a lot of people in the Cascades, in the Pacific Northwest, like to use, that has three stripes of colors — and it’s commonly referred to as “the Doug” for similar reasons. So Douglas Fur will be the name of this dog. Its nickname would probably just be Doug. Or Dougie. Unless it’s in trouble. In which I would say its full name.

Portland doesn’t have a ton of professional sports teams, but it is fanatic about the ones it has. Here’s Portland Timbers soccer fans displaying the Cascadian flag, “the Doug.”

Paul: I like your answer a lot. For me, I think Portland would be a total mutt. I think it’s too weird to be just like a single proper breed. I think there’s times when it just like goes nuts and has like total puppy dog energy. Really kind of reminds me of the derpiness of my brother’s dog, who is a full poodle. I feel like there’d be a little bit of poodle in there for sure. There’d also be a little bit of schnauzer — just like fun and goofy and likes to wrestle with you. And it’s a little smaller, like the size of the city. But they’re probably both super high energy but then just will sleep in your bed for 12 hours at a time. And snuggle with you.

And his name would be Willikers. Yeah. I don’t have any of the strong reasons that you do. But don’t you think Willikers would just be a great name for a Portland-based mutt dog? That’s a great dog.

Annie: would you call them Willikers all the time, or is there a nickname there?

Paul: No I think it’s just Willikers. And then when you’re mad you’re just like GEE WILLIKERS!!!! Wish you wouldn’t have gotten into that trash!!! Feels very fair that Willikers would probably get into trash a lot.

Photo by Matt Nelson on Unsplash

Q3: You have $50 to spend in a day in Portland. How would you spend it?

Paul: I’m going to chart through the course of a day a little bit. This isn’t just one thing. So I think one place to start is maybe the most touristy part of Portland, which is right around Old Town, where there’s Voodoo Donuts and there’s also this oyster bar. You could either get a Voodoo Donut to start your day off, or you could get an oyster shooter, like I did. This was basically a shot of whiskey with an oyster inside. It was delicious. That’s a breakfast of champions.

Annie: So this is like, 10 AM?

Paul: That is correct. It’s the beginning of your day. Yes. So then, you want to bike from the west side over to the east side. And find yourself in this little place called Next Adventure, which is an outdoors shop that has this bargain basement with all kinds of cool deals. You probably want to get a good shirt of some kind, and you can get one for like five bucks. Yeah, it’s super cheap, and it’s gonna come in real handy.

Photo by Jae Park on Unsplash

From there, I think you want to go to this awesome used bookstore called Mother Foucault. Shout out to Jackson for recommending this place.

Annie: Our friend Jackson, not like, you know, the city of Jackson.

Paul: Correct, not the idea of Jackson, not the religion of Jackson. (Although Jackson, if you did want to start your own religion, you probably would have some success with that.) But yea I’m talking about the bookshop, and it’s used, and they’ve got a crazy selection of all sorts of stuff. So, whatever your fancy is for the day, you can probably find a pretty great book for five bucks. Maybe it’s a very common novel, maybe it’s about the hidden history of Portland.

At this point, you’re like 15 bucks in and you’re probably getting a little hungry, a little thirsty, you’re in need of something. So I think what you want to do then is bike up to the Alberta neighborhood, and you want to go to Great Notion Brewery and get a beer. Probably an IPA because literally every brewery in Portland has seven different kinds of IPAs and they’re very solid generally. And you also want to get a taco or two from Matt’s BBQ Tacos, which are just heavenly and delicious.

Annie: These tacos are inside Great Notion.

Paul: Yeah, this is the one-stop shop for all of the hedonistic pleasures. So you’re going to be satiated, you’re going to be happy there. I think what you want to do after is go and gather some groceries, probably go to a little local farmers’ market of which there are many in Portland. You want to get some berries? You want to get some simple sandwich stuff? And then you can go to your place of choosing to watch the sunset. Maybe you want to go by Steel Bridge, and get great river views. Maybe you want to go up to Mount Tabor and have yourself a nice little picnic. You’ve got your book in hand and at this point you’ve spent fifty dollars on: a book, which you get to take with you; a shirt, which will help keep the memory; and a number of delicious things inside your body that you will not soon forget.

Photo by Elena Kuchko on Unsplash

Annie: That is a very lovely day you just described! And i think as you were talking, and as I was thinking about my own answer to this question, one thing that was very clear to me is just that there are so many awesome things you can do in Portland that are totally free. Like, it’s a city with really incredible scenery and nature. Amazing hiking trails. 12 beautiful bridges. And so bikeable. All of which cost zero dollars.

I didn’t go into a full day like you did. But for 50 dollars, one thing folks might not know is that Oregon does not have sales taxes. So the price is the price. Obviously at restaurants you should tip, but otherwise what you see is what you pay and that’s pretty amazing. This helps make prices generally pretty reasonable in Portland, at least compared to the Bay Area.

All right, so 50 dollars. I would first go to Powell’s Books. It’s more touristy than Mother Foucault, but also giant. I think it’s the largest bookstore in the U.S.

Paul: I think it’s the largest bookstore in the galaxy. I hear Mars had a large bookstore, but then Powell’s added a few more floors.

Annie: Yeah, that’s what I heard too. Anyway, Powell’s Books is an entire giant block of books, truly amazing, and they have some used books there too, so you can spend 10 dollars and get yourself a nice book. Then from there, Next Adventure is also on my list. It’s basically the local REI. And yes, you must go to their bargain basement. You can spend $15 and get like two or three pretty good items, like a really nice exercise shirt, maybe even a Patagonia jacket.

Photo by Kevin Butz on Unsplash

Then I have Kachka next, which is not too far from Next Adventure actually, in the Southeast quadrant. I think it’s one of both of our favorite restaurants that we went to in Portland. It’s a Russian restaurant, and for $15 for one person, you can eat really well there. Make sure to try their little dumplings!

Then, I would actually also bike to Great Notion Brewing next. Going to Great Notion is always a great notion. Seven dollars gets you an amazing beer on tap. If you are following the math, you actually still have a few dollars left over at this point to play with. So I didn’t even use up the full 50 dollars. And you’ve had an amazing day with a lot of good eats, good drinks, good adventures, good purchases.

Go get a beer here

Q4: If an asteroid was coming to hit Portland, what quadrant of the city would you save?

For those unfamiliar with Portland: often people talk about it in terms of its four quadrants: Northeast, Northwest, Southeast, and Southwest. The Willamette River divides the east and west. Burnside St divides the north and south. Some people also talk about the “North” as its own section, although the word “quadrant” doesn’t quite make sense anymore with that in mind.

Paul: So obviously I’d try to save the whole city, but the parameter of this question is you can only save 20% of the city for some reason. In that case, I would save the Southeast. I think there’s so much in the Southeast that’s really cool. There is just a ton of restaurants which we went to. I think there are a lot of people there too. I think it’s actually the most populated part of Portland, so you’re getting to save the majority of the people, which is quite important.

But also, the Southeast was just my favorite general neighborhood too. It’s nice to ride around down there, and it felt like it had a nice combination of tasty foods and good breweries. Also, our very favorite outdoors apparel store, Next Adventure (already mentioned multiple times above), is there.

Photo by Slava Keyzman on Unsplash

Annie: I think I maybe interpreted this question or at least went about answering it a little bit differently. I like that you thought about saving as many people as possible. That was not at all something that I considered…

In fact, I very specifically picked the Northwest because Forest Park and therefore a lot of trees are in the Northwest. It’s not that I don’t care about human lives (I do). But it takes a lot of time to grow trees! Forests take a lot of time to nurture! Actually a reason that one of the many nicknames of this city is Stumptown, is that this entire region actually used to be miles of miles and miles of forests, and when people came to Portland to settle here, they actually chopped down a ton of trees. People have since rebuilt up Forest Park, which is this amazing place — you feel like you’re in the middle of a huge, wild forest in the middle of a city. It allows people in Portland to have really easy access to this incredible area of nature.

So yea, I would choose to save the trees. Sorry, humans.

Peeking through Forest Park at St. Johns Bridge

Q5: If you could wave a magic wand and change one thing about Portland, what would it be?

Annie: Okay, this is not literally possible, but since we’re talking about magic wands and all, I would want there to be less rain. Rain is such a core part of Portland, and I fully acknowledge that the copious amount of rain is probably what makes Portland and this region in general so beautiful…

Paul: Yea the rain is probably what makes your beloved Forest Park so green.

Annie: Yea for sure, sorry trees.

The amazing amount of nature and produce here (people always talk about the “bounties of Oregon”) is probably directly caused at least in part by the amount of rain. So this answer is obviously not taking that into account, but just for Annie, who loves the sun and warmth and doesn’t exactly like to be covered in rain most of the time, that’s what I would pick to do with my magic wand. Because to be honest, for me personally, one of the main drawbacks of Portland as a place to live is that it gets so much rain.

While we were living there in July, there was zero rain (it was literally sunny and gorgeous the entire time we were there). So this is more just me knowing and hearing from others that other seasons here are really rainy, and people can get seasonal depression, etc. So if I got to just wave a magic wand and change anything, that’s what I would change. Sorry, trees. I really had to pick trees over people in my last answer, and now I’m picking myself over trees, apparently.

Photo by Jaunt and Joy on Unsplash

Paul: I think one of the things that a lot of West Coast cities have really been struggling with over the last few years, particularly since COVID, has been that there’s just a really large unhoused population and not a lot of affordable housing. Homelessness is not an easy thing to solve at all. So I think a magic wand is a great opportunity to try to experiment with some things. And I think if we could just create an abundance of really affordable housing, that could solve a number of issues. That’s one of the first things that locals here talk about as well, especially compared to some of the earlier versions of Portland.

Annie: Yea, I think when we first got to Portland, we were surprised by how comparable the level of homelessness and mental health crisis here seem to be to the Bay Area, because i think the San Francisco Bay Area is almost notorious for this issue. So absolutely agreed with what you’re saying about affordable housing.

Paul: Yeah. And I think we felt it pretty directly too because the place that we were staying at was right by the river. The apartment complex itself is fairly nice, but I think the Chinatown area (where we were staying) had probably the thickest density of homelessness compared to anywhere else in the city. So it definitely was something that we felt every single day.

Photo by Eric Muhr on Unsplash

Q6: Portland is, in many ways, a fairly unique spot in the state of Oregon. It’s the biggest city in the state, with all that comes with that. We did intentionally go out and explore some areas outside of Portland too, like Astoria, Cannon Beach, going white water river rafting on Clackamas River. What was your impression of the rest of Oregon?

Paul: So I think Oregon is probably one of the most naturally beautiful states. And I think that’s saying a lot as someone who grew up in Wyoming, which is very much an outdoorsy state, and as someone who lived in California for 14 years. I think Oregon just has such diversity in terms of geography.

Like you said, we went and saw beautiful Cannon Beach, and went to Astoria and got to see these really jagged dramatic coastlines, and also rainforests that basically grew right up to the coast and created these really unique landscapes. And right now, literally as we’re driving, you can see these yellow prairie fields for miles and miles, and it’s a totally different world out here. And then we went up to Mount Hood one day and it’s an active volcano.

View from Astoria, Oregon

So the amount of diversity and different kinds of beautiful outdoors really, really stick with me, you know. And Oregon is full of people who really love getting out and enjoying nature. And I think Portland’s an interesting place because it’s a city that is super close to all that nature. Like you can drive 30 minutes and it feels like you’re not in the city at all anymore. Like we saw a bunch of Chuck Norris billboards that were advocating for funding the police, which is very much not a Portland political position.

Maybe it’s similar to Denver, where Denver is very much a city but in a state that’s fairly rural. But otherwise, I found that to be really striking and is in my mind a huge, huge benefit — where you get to both enjoy living in a city and being surrounded by culture and to some degree diversity of people and ideas, but also you can get out and experience just a vast number of different outdoors activities. So that’s the thing that predominantly sits in my mind: Portland is very different from the rest of Oregon, and it gives you a full picture of life that I think can be really exciting and really cool.

Cannon Beach, Oregon

Annie: Yeah. Totally. By the way, you’re not the only person who thinks that Oregon is one of the most naturally beautiful places. My gynecologist (who’s from Portland) also thinks that. So it must be true.

I actually also totally agree with that. In a relatively small area, Oregon has so many different natural areas, huge spans of forests, beautiful rivers, deserts, volcanoes… all within really easy access. So I very much share that perspective, and to me it’s mostly a pro of living in Portland. Portland is a progressive, relatively multicultural, super walkable and bikeable place, but you also have really easy access to completely different landscapes.

We went berry picking on Sauvie Island, which is just 10 miles from downtown Portland but a completely different landscape (much more rural)

One thing that gives me a little bit of pause about Oregon as a state, is that it’s not very diverse from a demographic perspective. Before we came to Portland, a lot of people told us that Portland is really, really white. And that was one of the things that we were a little worried about. And in the last month, in Portland itself, we’ve actually been pretty pleasantly surprised by the level of diversity, in terms of people we saw in the city, diversity of food, etc. However, I think the rest of Oregon is a pretty different story. People in Portland would honestly be the first to to remind folks that for a long time, Oregon as a state wanted to be a white utopia, and that its constitution was pretty blatantly racist until honestly not that long ago. So Oregon definitely has, I think, a really racist, problematic history. I guess that’s not necessarily unique to Oregon, but I think you still have some of that in parts of the state even just 30 minutes outside of probably one of the most progressive cities in the country. And I think that will be something to get used to, if we choose to live here.

White water river rafting on the Clackamas River

And finally… our five favorite restaurants in Portland — jointly decided!

First of all, food in Portland is SO, SO GOOD. I don’t know if I’ve been to another city that matches the creativity and quality of PDX’s culinary scene (and I feel like I’ve been fortunate enough to have visited many world-class food cities!). So it was not easy to narrow down all the mind-blowing restaurants we went to, to just five. That’s partly why there are two honorary mentions also. Consider these our top food recommendations for Portland!

Langbaan, in NW Portland

In no particular order:

  • Kachka (SE): Russian cuisine. Paul may have cried from pure gastronomic joy at this restaurant. We especially loved their dumplings and cod liver buterbrodi. Their horseradish vodka was also an experience. An absolute must-try in PDX.
  • Langbaan (NW): By far the fanciest restaurant we went to. 12-course Thai meal where somehow every. single. dish was amazing, creative, and a blast for your taste buds. We got to sit right in front of the kitchen and watch the chefs work their magic. There are some higher-end restaurants that are fun to go to but ultimately not quite worth the price. This is not one of those restaurants.
  • Broder Cafe (SE): Scandinavian brunch that straight up blew our minds. We got the Swedish hash with house-smoked trout, and their Norwegian potato crepe. And I still dream about them. There was a long wait, but they made that significantly more pleasant by letting you have unlimited (and really good) free coffee while you wait.
  • Matt’s BBQ Tacos (NE): Matt’s BBQ is a famous BBQ food truck in Portland (in a great food truck pod on Mississippi Avenue — an area that we absolutely loved). Matt’s BBQ Tacos is, as they very aptly describe on their website, “Matt’s BBQ but in tacos.” And it’s basically the best? Also the location we went to is inside Great Notion Brewing, our favorite Portland brewery, in the Alberta neighborhood.
  • Scotch Lodge (SE): People generally know this place for their inventive cocktails and dark library vibe — which we can attest are fantastic in their own right. But what catapulted this place into our Top Five was their food. And specifically, their seaweed butter pappardelle with candied duck. Holy *uck.
  • [Honorary mention] Bing Mi (NW): An unpretentious food truck in the NW 23rd Ave area (another super fun neighborhood) that serves up a creative spin on the traditional Chinese jianbing 煎餅. Delicious, fun, not-too-heavy hand-held food!
  • [Honorary mention] Eem (N): In the true Portland style of mixing things that few others would think of mixing, Eem is the marriage of Matt’s BBQ (mentioned above), Langbaan (mentioned above), and great cocktails. The result is creative Thai BBQ dishes (like white curry with burnt ends) alongside fun cocktails. Expect full food coma afterward.