We found a great flight deal online (Frontier, $160 per person) and decided it was time to visit a city we had never been to before: Portland.
For this trip, we decided to try Vrbo instead of our usual Airbnb. We had always booked Airbnb in the past, but this time Vrbo happened to be cheaper. Our place was in the Sunnyside neighborhood, about a mile east of downtown Portland. Portland seemed small enough that, unless you planned to walk the entire city, the exact location of your stay didn't matter too much. I felt our location was convenient, but it also meant we had to figure out what there was to do around us.
It was a such a short weekend trip and we didn't plan on doing too much. We really didn't have a plan at all. So, we simply walked around the neighborhood near our place and decided to see where the day would take us.
Our first stop was a coffee shop. Somehow, we ended up at Stumptown Coffee Roasters.
We had never seen this coffee shop back in Los Angeles, so we decided to go inside. I don't usually drink coffee, so my wife ordered a coffee while I stuck with ice water.
But then I smelled the coffee.
The aroma was so good that even I started thinking maybe I should have ordered one. My wife, the real coffee expert between the two of us, loved it. She liked it so much that she wanted to buy some of their beans to take home.
Few hours later, we also stopped by Dapper & Wise Roasters. There were wooden tables sitting in front of a huge glass window overlooking the street. It was lightly sprinkling outside, and sitting there with my wife, watching the rain through the glass, felt incredibly cozy.
A Little Portland Brewery Hopping
After coffee, we decided it was time to explore more of the city. Since we didn't have a real itinerary, we figured brewery hopping would be a pretty good way to experience Portland.
We visited Steeplejack Brewing, Burnside Brewing, and Deschutes Brewery.
Steeplejack Brewing Company
Steeplejack Brewing caught our attention right away. The brewery is inside a beautifully restored old church, which gives it a unique atmosphere. The tall wooden beams, stained-glass windows, dark wood, and high ceilings make the place feel warm and spacious.
The bar had plenty of taps and a good variety of beers. There were different styles to choose from, including cask and nitro beers, so there was something for everyone.
We really enjoyed the atmosphere here. It felt like more than just a brewery. It felt like having a beer inside a historic Portland landmark. The beautiful interior and good beer selection made Steeplejack one of our favorite brewery stops in Portland.
Burnside (Permanently Closed)
Burnside was especially memorable because of the large black stainless-steel barrel outside. It immediately caught our attention and made it easy to know we had found the place. Apparently, the place is permanently closed, following financial troubles. Ouch!
Deschutes Brewery
There’s something special about stepping into a place that feels both lively and familiar. Deschutes Brewery’s Portland Public House captures that feeling perfectly.
The first thing that hits you is the energy of the room. People gathered at the bar, jackets still on from the Portland weather, the low hum of conversation filling the space. On the table sits a cold pint of Deschutes beer, golden and inviting, next to a plate of grilled sausages, braised cabbage, and thick slices of bread. It’s the kind of simple, satisfying pub fare that pairs perfectly with a good IPA.
Outside, the brewery’s distinctive black-and-gold sign stands out against the brick building, with the “Inversion IPA” lettering visible above the windows and a modern high-rise rising behind it. Inside, the space opens up into a warm, industrial-chic room with deep red walls covered in framed photos, maps, and memorabilia. Copper brewing equipment and rows of taps line the bar, while patrons lean in for another round.
Even the small details feel intentional. A classic black-and-white Deschutes coaster resting on the wooden table, the mountain-and-wave logo as recognizable as ever. And of course, no visit is complete without a soft pretzel and a side of creamy dip, ready for sharing (or not).
It’s the kind of place that makes you want to linger a little longer, order one more pint, and soak it all in.
At this point, Portland was turning into a pretty normal weekend trip.
Coffee. Breweries. Walking around the city.
And then we found Le Pigeon.
The Unexpected Dinner at Le Pigeon
We were walking down the street when we noticed a restaurant that looked beautiful from the outside. Something about the interior caught our attention, so we decided to see if we could get in.
There was one problem. We didn't have a reservation. We figured there was no chance. But then we learned that two corner seats at the bar were available. Perfect.
And this wasn't a typical restaurant bar where you sit and watch a bartender make drinks. The seats were positioned directly in front of the open kitchen, so we could actually watch the chefs prepare the food.
We sat at the corner, each on one side of the 90-degree angle, which actually worked out perfectly. We could see each other while also watching the kitchen.
Then the food started coming out. Everything was beautifully prepared. I still remember the feeling when I ate these food. That first bite made me think, Hmm... that's really good. Then another bite. And another.
It was the kind of meal that makes you want to keep eating even when you're already full.
The food paired beautifully with the wine, and I especially remember the black truffle. The aroma hit us before we even took a bite, and the flavor stayed with us afterward.
But the food wasn't the only memorable part of dinner.
Meeting Two Strangers Who Changed Our Night
We started talking with the couple sitting next to us.
They were engaged, and their wedding date was already set. We told them we were visiting from Los Angeles and were simply wandering around Portland, trying to figure out what to see and do.
Then they offered to show us around the city. We thought they meant they would tell us about some places to visit.
We were wrong.
They were actually willing to take us around themselves. We were ready to follow their car to the next destination, but they invited us to ride with them.
He offered to drive.
We got into the car without much hesitation, but I had to make one comment:
"My mom told me not to get into a stranger's car!"
Everyone immediately cracked up. And just like that, our completely ordinary Portland trip turned into something very different.
Dreams, Dancing, and Mud Pie
His music selection in his car was exceptional.
He started playing "Dreams" by Zhu & Nero, and that song somehow became the soundtrack of our Portland trip.
We listened to it over and over long after we returned home. Maybe it sounded especially good because of the moment—the excitement of being somewhere new, riding around with people we had just met, and having absolutely no idea what the rest of the night would bring.
Whatever the reason, the song stuck with us.
Our new friends took us to an open-air club, where we hung out, danced, and had a few drinks. I honestly don't remember the name of the club. But I remember having fun.
The restaurant was called The Montage, so we followed them there just for dessert. The mud pie is something that you must try. We will come back in a heartbeat. If you are in the town, you should definitely go.
And that's when I realized how different this trip had become.
How else would we have known about these places?
We had no itinerary. We didn't research them beforehand. We simply happened to sit next to the right people at dinner.
We spent several hours together—restaurant, club, dessert, and driving around Portland. They were complete strangers when we sat down for dinner. By the end of the night, we felt like we had made new friends.
Would We Go Back to Portland?
The next day, we barely made it to the airport and eventually headed back home.
It was a short trip, but whenever we think about Portland, we don't really remember the breweries or even the coffee shops first.
We remember that night.
We remember sitting at Le Pigeon, meeting a couple who were about to get married, getting into a stranger's car after joking about what our mothers had told us, listening to "Dreams," dancing at an open-air club, and finishing the night with mud pie.
*Le Bistro Montage permanently closed its brick-and-mortar location in June 2020 after 27 years in business. The iconic late-night Cajun restaurant shut down due to severe financial strains brought on by the COVID-19 pandemic and the inability to sustain operations under early pandemic restrictions.
That's what I love about traveling.
Sometimes the best memories aren't the things you planned.
They're the things you never expected to happen.
Would I Go Back to Portland for a Weekend?
Absolutely.
If I could get a reservation at Le Pigeon, I'd go. Of course, the coffee and brewery hopping were also so much fun. Why would you want to skip those?
And if I could somehow meet those two wonderful people again, I'd go without hesitation.
Sometimes a city becomes memorable not because of what you planned to see, but because of who you happened to meet along the way.
LET'S GO!