Our Waiter Wore a Chain: Day One in a Fading Echo of Portlandia

August 4, 2025. Portland, Oregon.

When I told people we were headed to Portland for our 2025 Family Adventure, the common reaction was: Why? Even Dom, once we arrived, asked more than once: What were you expecting to see? Their skepticism made it seem like Portland was just a random choice, as if I’d closed my eyes and jabbed a finger at a spinning globe. But it turned out to be a perfect fit—fun for the kids, scenic enough to make Dom smile, and full of unexpected bucket-list moments I didn’t know I had.

Our options were limited this year since Matador and Rainbow didn’t have passports (a situation now corrected). We thought about another LegoLand-type trip, but Matador vetoed anything involving Disney or costumed adults. East Coast spots like Bar Harbor and nearby destinations like Lake Tahoe had their appeal, but Portland won with its mix of nature, zoo, science center, and—most importantly—cooler August weather than Texas.

Fueled by my Goonies and Portlandia knowledge, I booked the hotel and flights, and off we went.

As we boarded the plane in Austin bound for Las Vegas, I encouraged Rainbow to say hello to everyone we passed, including the flight attendants and the pilots. To my amazement, both she and her brother were then invited to sit in the cockpit, something I thought would never happen for them since terrorists ruined everything. Isn’t the cockpit supposed to be secure at all times? Are you sure you want my eight-year-old son turning random dials?!

It was a moment I never saw coming and will likely never see again. I took a thousand pictures, and the joy on their faces is so beautiful, even if they don’t fully understand how rare this experience is. Of course, Rainbow does have a habit of opening doors for us.

“That’s why you have girls. Two boys? No way. Get to your seat, punks. Charming daughter? Come in, take the wheel, these planes pretty much fly themselves…” – Billy

Although I offered to swap, Dom sat with the kids on both legs of our trip to Portland, with Matador by the window on his Switch and Rainbow in the middle seat with her headphones and pink iPad. I sat across the aisle next to a younger guy who boarded late and took the middle seat, saying, “Alright, three broad-shouldered men sitting next to each other.” It was prophetic in a way I didn’t realize at the time.

The experience I had on that flight would be repeated on the other three: me leaning against the aisle armrest, unable to sit back in my chair, holding a copy of Richard Matheson’s What Dreams May Come a few inches from my face. The older I get, the more uncomfortable planes become, and the more I wish I had sold more books so I could afford business class tickets.

That said, the book really made time fly.

We landed at a remote terminal at Portland International Airport, and due to some construction, had to make a long walk to the exit. Signs painted on the walls said Baggage Claim – 9-minute walk, which made me appreciate Dom’s insistence that we bring Rainbow’s travel stroller. I can’t imagine how long it would have taken her little legs to traverse that distance, or worse, how I would have fared if I carried her.

PDX is beautiful, and of course, I took no photos of the inside. The ceiling is comprised of wooden beams frozen in an undulating wave, which is just entrancing enough to make you forget you’ve been battling air travel for the last six hours. We walked for what felt like miles, found our one checked bag, and headed outside.

“This is their summer?” asked Dom.

The temperature was 74 degrees with a light breeze, and our Texas-acclimated bodies soaked it up. The sun, much like in San Diego, didn’t feel like a red-hot poker ready to stab me in the face, and the wind made it feel even cooler. Two things became evident to us immediately. First, this is how summers should be.

And second, we live in the wrong state.

This sentiment would be echoed a thousand times over throughout our trip, and it never stopped being less true.

Portland is a beautiful city, a fact we commented on even as we left the airport. Instead of mile-wide interstates, Portland’s highways are small, three lanes at most, and weave in and out of the landscape. In Texas, we talk about the horizon the same way we talk about the moon: distant and unreachable. There is no horizon in Portland, just mountains and forests and modest buildings unconcerned with providing tech bros expensive apartments in the heart of downtown.

Speaking of downtown and how it contrasts with Austin… even though most of the streets were only two lanes wide, the claustrophobia wasn’t too bad. It’s probably less a function of the design and more of the people themselves: not every drive on the road was an angry SOB. That makes a huge difference in close quarters. Step off the curb in downtown Austin, and that step might be your last. Here, cars actually stop for pedestrians, especially if they’re waiting patiently to cross.

Some streets didn’t even have stop signs, yet cars stopped on their own. I’m guessing it’s a city or state law, but to a visitor, it smacks of kindness. Which is… weird?

A few other observations:

• Downtown Portland doesn’t smell overwhelmingly of urine and sweat
• The unhoused population doesn’t accost you at every corner. Of the dozen or so we encountered while walking downtown, none even looked in our direction.
• People were actually running and biking downtown. And not just dudes out for their morning run, but families and young kids riding bikes with training wheels, almost as if downtown is a safe place.

After a long day of travel and hotel rooms with flooded bathrooms, we headed out into the city to find some dinner. Two nice things happened on our trip: I parallel parked like a boss, and I always picked good restaurants. Then again, everything we ate was wonderful, so maybe it was just hard to choose poorly in downtown Portland.

Our first culinary experience was at Piattino, a small Italian restaurant on the corner of Everett and 12th. Inside, the lighting is warm and dim enough to flatter anyone, even a tired family of four who desperately need showers. What is surely locally sourced wood panels the walls, and there is a small pizza oven that anchors the room, glowing like it’s somehow aware that two children just walked in. The tables are polished slabs of wood on steel frames; ours sat upon a reclaimed sewing table, complete with a working treadle.

Everything was beyond good. Pizza, pasta, carbonara, calamari… there wasn’t a bad morsel in the bunch. We sat inside, and from my vantage point, I could see out into the street, to the tables that had been set along the sidewalk. That’s when I first noticed our waiter was wearing a chain. Not the little golden ones we used to wear in high school, but a “secure your trailer to your F150” sort of choker. That was when I remembered Portland was supposed to be weird like Austin (used to be), and it got me thinking: which city faded first?

I pondered this as we paid the bill and headed back to the hotel. The closest I could get to an answer was that Portland was Austin fifteen years ago, before the arrival of Google and Meta and, gag me with a fucking spoon, Tesla. I was in a fading echo of Portlandia, but even that was warm and inviting. Things were different, it felt different, and I don’t know if that made us feel good because it was somehow better than Austin… or because it was not just more of the same.

Other observations from Piattino and restaurants in general:

• You rarely get ice with your drinks. Even my Old Fashions didn’t have the single big block that I’m used to.
• Crayons are communal. If you want a four-pack of crayons individually wrapped in plastic, you need to stay in Texas.
• One restaurant, Cheryl’s on 12th, even gave the kids coloring books that were half-filled already.
• Conservation, recycling, and reuse are big here, and Dom and I nod in approval.

As we settle in for our first night away from home, we realize we don’t have a nightlight or a noise machine. No worries though. We’ll just do a Target drive-up.

“They have Targets in Portland?!” asked Matador.

“Yes, my little monkey. They have Targets everywhere.”