By: Erin
Posted: February 13, 2026
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Every year, Mandy and I try to take a trip somewhere we’ve never been. That’s the cool thing about being adults with (a little) money. It started with a trip to Louisville, KY, and just kind of became a tradition after. Look at a map, look at a cool city, figure out what to do there and how to get there.
I don’t remember exactly how Portland became our destination of choice. I know we both wanted to visit the Pacific Northwest, since neither of us had been on the West Coast before, and Mandy and I had been writing stories set in the Portland and Seattle areas, so getting some real world experience in the place we had been writing about was appealing. I think learning about the massive video rental store Movie Madness was the clincher, and it helped that we had friends in the area we were hoping to meet up with.
During the trip, I was taken by the idea of filming a few vignettes here and there with the intention of editing them into a vlog. We drove to the airport listening to one of my favorite albums, Stepdad’s Wildlife Pop, and the spirit of adventure possessed me. As soon as I stepped into the parking lot I shot some film and took some photos, and that persisted throughout the trip. It took me a year to back up all my photos and videos, and I finally got off my rear end and made the planned vlog happen! You can watch all 15 minutes of our hundreds of photos and little videos after the cut.
It’s not much, but it’s cute!
Portland was incredible. It was a beautiful, freeing city absolutely teeming with life. From the moment we arrived at the Hotel DeLuxe to see pride flags flapping in the breeze we knew we were somewhere special.
Our flight from Cincinnati was a rather fun one – I accidentally bought $50 worth of pick-and-mix candy because those Facebook shorts had me craving, I left my headphones at home and bought a new pair from a vending machine that I’m still using to this day, and I broke out my old iPod Touch because I didn’t feel like dealing with Bluetooth connectivity (which spiraled into a whole other thing…). It was great. We landed in Seattle, and then flew to PDX, and arrived late at night. Our trip officially started the next day.
We were very excited to arrive.
We picked the Hotel DeLuxe because it looked like something out of BioShock. The art deco flourishes complete with black-and-white stills from films felt just right for us, and the bar and restaurant was an added bonus, to say nothing of the great downtown location. It was a comfortable hotel, and the aesthetic was very charming. More importantly, the room was quiet, the bed was comfortable, and even if only two or three of the TV channels worked, one of them was History Channel and it played a marathon of some ridiculous show about the history of Little Debbie snack cakes and other uniquely American brands, so we had a great time there.
One thing we love to do on our first day in a new city is to get up early and take a walk. I remember the first thing that struck me was how the street signs and crosswalk lights looked. Very square! We wandered, finding community libraries, a school football field, and a large amount of homeless people.
Yeah, the second thing that struck us about the city was that there were a lot of homeless people and encampments on street corners. It’s a sad situation, one that really laid bare how the country is failing the vulnerable and its own people. It made for a stark contrast between the vibrant city life that popped up as the day went on and the plight of the disenfranchised. A city of contrasts, with gorgeous architecture and centers of culture serving as the backdrop for a population that deserves better care – or any care at all.
On our first day we went to a grocery store down town, picking up staples that we loaded into my Sonic the Hedgehog cooler I had gotten for Christmas the year before. This was going to prove invaluable, because while food was generally affordable, our hotel gave us credit for breakfast but it wasn’t completely free. We also did a lot of walking, so having a readily-available case of water helped a lot as well. The hotel offered bicycle rentals, but we didn’t go for it.
We hadn’t planned on meeting up with our friend Nova so quickly, but she was free and we were free, so we made it happen! We met in front of the famous rental store, Movie Madness, and through that adventure learned how to use the bus system! Public transportation is the coolest thing in the world, and being able to grab a bus wherever we wanted was great. Meeting Nova was an absolute treat, and we got to tell her to watch Baby Assassins and gift her a copy of WarGames, so I would say it was a job well done. We ate at a location close by that had several food trucks, explored the movie store more, saw the famous Fight Club Soap in person and even saw a real statue used in a scene from Citizen Kane! How cool is that?!
Sadly, there was no cane from Citizen Kane.
At some point during the day we got lost in Powell’s Books, a massive book store that author Edgar Cantero has written about in one of my friend Leah’s favorite books, This Body’s Not Big Enough For Both Of Us. Apparently he sometimes sneaks signed copies of his books into the store, but no dice this time. I bought a copy nonetheless and should really read it one of these days.
At Everyday Music we found rows and rows of bargain CDs and tons of vinyl I could not afford. I was picking up CDs from Shamen, The World/Inferno Friendship Society, Smash Mouth, and BT from anywhere between 99c and $5. It was amazing! And let me tell you, those albums came in handy when I rebuilt my music library on iTunes. I even found and bought an original Criterion Collection DVD of This Is Spinal Tap, and I now proudly own that along with my original Blockbuster Special Edition DVD and the newest Criterion release. I never wanted to leave.
One place we were told to go was Voodoo Donuts, and it did not disappoint. Walking through the city in the morning and searching for donuts was a lovely experience, and something I fell in love with as we did so was how much graffiti and art there was over all the walls and sidewalks. Murals, patterns, concert posters, and stickers decorated every surface, from bright rainbow walkways, to tributes to those tragically lost to police brutality, to heavily-decorated food trucks and the lurid pink facade of the store we were looking for. Portland is a city of artists of every stripe, and as someone who loves the city life, I could feel the buzz of creativity and passion around me even at 7AM.
We even, completely accidentally, found the famous Keep Portland Weird sign on our way.
It has hard to choose what to get from Voodoo Donuts, but I think I could have done worse than a Cap’n Crunch donut.
One place that we visited and still to this day can’t stop raving about? The Living Room Theater. We bought a whole meal and cocktails at that place, went to a screening of Poor Things (which we loved!), sat in armchairs, and had an absolutely incredible evening. Next time we’re in the city, we’re going back. I don’t care what we watch.
My favorite thing about Portland was how walkable a city it is. This was never more evident than the day we met another friend of ours, Alternis. Alternis was a local who had been in the area longer than Nova, and he suggested we go to the science museum OMSI. As museum lovers, Mandy and I were raring to go, and even though he had a car we decided to walk all the way across a huge bridge and into another section of the city to get there. It was amazing. Not only was the museum a ton of fun, but earlier in the day Mandy and I had went to a thrift store and got some spam musubi and discovered a really cool place that served chicken katsu. The three of us walked, talked, and saw all kinds of dinosaur skulls and cool reptiles and rocks, and then we walked all the way back across the bridge and ate some katsu sandwiches. Alternis, it turned out, was a soda connoisseur, so we stopped by a vintage soda fountain and candy shop as well so he could check out the interesting available flavors.
He was happy to show us around the city he had visited plenty of times growing up, and he took us to some great video game stores, including one that had a vinyl record of Tekken 7 featuring my girl Alisa Bosconovitch (which I didn’t buy) and a bunch of wireless modern N64 controllers (which I did). We ended the day with some ice cream from Salt & Straw, a local place that does unique flavors. I don’t even remember what I ate, but I remember it being delicious.
Jupiter was much smaller in-person.
We met with Nova again on another day to visit Portland’s famous Japanese Garden. It was an absolutely brutal hike up a hill to get there, and the Rose Garden wasn’t in bloom, but the actual Japanese Garden was utterly stunning. We started our day visiting Japanese stores in town, as the city has a large immigrant population, and then we basked among the cherry blossom trees, observed the koi pond, looked at beautiful photography of Japanese locales, admired the view high above the city, and generally had a truly peaceful, truly meditative time.
We then decided to visit TOTL Games, an unassuming little store that somehow had a life-size Naked Snake statue, a Hello Kitty Dreamcast, multiple copies of every Xenosaga game, and a repro cartridge of Streets Of Rage 2 But With Rick From Splatterhouse In It. That was an easy buy. Unfortunately, we got lost trying to figure out the bus system and nearly made Nova late for work, so we had to get a Lyft back to town. It was very funny, but I felt bad. She was cool with it, though.
The most peaceful place on Earth.
One funny thing about Portland is that they love brunch there. They have so many restaurants specially serving brunch. It’s to the point that one of the pieces of graffiti we saw proudly proclaimed “Fuck Brunch, Eat Shit”. On the day we went to the Japanese Garden, we started at Hunnymilk and had a great meal. Maybe it’s bougie, but I understand the hype behind brunch.
Portland’s food truck scene was not to be trifled with. We had gotten a taste earlier during our trip to Movie Madness, but the burrito I got from Tito’s Burritos #2 (in a plaza loaded with food trucks!) was to die for – and good thing, too, as my friend Carl (who had recently relocated from the West Coast) told me he would have been disappointed in his former part of the country if they had let me down. Fun fact, it was around this time that a major news story and scandal involving WWE and Vince McMahon dropped, so Carl and I were moderating a wrestling forum together and putting out fires while I ate a food truck burrito on vacation. Life is strange like that!
There are other places we went as we drifted through town – a pizza place at the bottom of a set of stairs in a building located between two streets, an arcade with a Soulcalibur 2 arcade machine, a memorabilia shop where we picked up a Japanese poster for David Lynch’s Dune, and a fancy restaurant where we had a lovely date-night-style meal – but my primary memories of those last days are ones of joy and freedom, of beautiful Spring nights, of a city steeped in history and queerness and culture, where people walked the streets at night, lined up for clubs, where corner stores with broken air conditioners had huge fans at their doors to keep the temperatures down, where bicycles lined the streets and everything felt just a little liminal. Our last night in Portland lasted a lifetime, and I felt so wonderfully blessed to be sharing it with my favorite person on Earth.
This may be my favorite picture of the trip.
The day we left, we decided to go back to Voodoo Donuts. They really were such good donuts. The sky was grey and the rain was gently coming down. It was nice of the weather to wait until we were about to leave to turn, because it blessed us beforehand. We sat on a wall, eating our donuts, when some kind of street security bot rolled down the road and absolutely terrified me. Mandy teased me about it through a mouthful of donut, but there’s something about automatons that either fill me with warmth or fill me with dread and I can never be sure which it’s going to be.
Our flight got delayed on the way back, and we landed with minutes to spare as we had to make a connection between airports. We did not make the connection, and we found ourselves in a completely empty airport at 11PM, fruitlessly banging on a door and watching our plane back to Cincinnati take off. We managed to get a flight back early in the morning, and so we ended our trip watching Food Network in a hotel on a frozen night and eating midnight Taco Bell.
I wouldn’t have had it any other way.