Portland, 2026

A brief moment to let the mask slip: it's been a real struggle lately.

For the last eighteen months, serious family health issues were part of our lives. These slowly became insurmountable on one side of our family, and we've spent most of the last three months trying to navigate an unfamiliar state. There are moments that life gets put on hold, with the hope that things will return to some degree of normalcy eventually.

Given all this, we had only managed one vacation in 2026, and we were striving to fix that before the summer vanished. After pricing out practically every destination I could think of – places we've never been, familiar cities, and foreign countries – the choice ended up being slightly predictable.

As best I can count from photographic memories, this is my eighth trip to Portland, Oregon. Often for vacation, sometimes for soccer, once for business, once solo to recover from a month of extreme burnout. Through life's quirks, we had not been to the city together since March 2022.

Of all our trips, this one felt like the best trip yet, a real accomplishment given how familiar my shoes are with that PDX carpet.

The trip had two chapters. The first half was a pseudo-make-up for spending our 24th wedding anniversary apart (see also: the aforementioned life getting put on hold). There was some quiet joy in Katie and I floating around the city together, spending time together in a way that has been pretty limited lately.

A city takes on a different shape when you're sharing it with someone new. For the third time, Stevie joined us for the back half of the trip, completing the chaotic trinity that is Team BestWorst. (This summer marked ten years of our collective friendship, so we'll call it a double anniversary sort of trip.)

The food scene in PDX remains hard to match, especially at a moment where NYC restaurants often feel in a death spiral.

Days later, I am still undecided about the best meal of the trip: our first night dinner at OK Omens (killer albacore crudo, luscious Dungeness crab salad)? Our first group meal at Yaowarat (those chive cakes! that char siu pork!)? Or just getting completely overwhelmed with food in the Han Oak backyard?

And there were stunning dishes everywhere: the miso-smothered katsu bomb of Tokyo Sando; a perfect pupusa serving as my breakfast at Doña Lolas; the pillow-like frites at L'Echelle; the creamiest cup of milk chocolate ice cream imaginable at Cornet Custard; even the perfectly balanced habanero aioli at Southpark Seafood, so good I contemplated taking a jar of it home.

The drinks, too. I loudly lamented the passing of Expatriate, and quietly morned the loss of Deadshot, but the cocktail scene is far from dead.

Pacific Standard is still punching far above its weight (those gimlets are fun, but are absolutely not "fun sized"). Creepy's did a victory lap for being named the town's best bar by spiking a Long Island Iced Tea with Midori – a clown move by my favorite clown bar. We were spoiled by a friend-of-a-friend at Multnomah Whisky Library, where the idea of an amaro latte being a great idea was forced in my head. We dropped into Collector before dinner at Han Oak and found a fun little program doing fun little cocktail things. And we didn't get enough time at Too Soon, but the program and space were both lovely and I've got it earmarked for a return visit.

I also dragged our group on short notice to an unassuming yellow house deep in SE, which hides Bible Club inside it. Calling it a speakeasy probably conjures a certain 2010s-mustached-bartenders-in-suspenders-dark-space-dealers-choice mental image. Bible Club takes the term literally: almost antique furniture and stemware, signs demanding the repeal of the 18th amendment, old time music wafting out of an ancient stereo). It was stunning and easily our best cocktail stop in a trip full of great bars. Put it on your lists.

That spontaneity became a running theme throughout the trip. I try to not overbook vacation days, because I love the ability to just throw everything on hold to chase an interesting lead. To wit:

Why is there a concert stage across from our hotel, and who's playing tomorrow night? A few scheduling changes and we found ourselves at the PDX Live closer of Vince Staples, adding a name that's long been rolling around my playlists to my Setlist account. (Shout out to local talent Wynne for a killer opening set.)

Why is TikTok showing me a video about the Log Lady from Twin Peaks? An easy schedule adjustment and we're heading to the World Forestry Center to celebrate Log Lady Day - we just missed the lookalike judging contest, but we did get free cherry pie.

Are those little funky donuts? Yes they are! I'll get three!

Does that store across the street have a skeleton in the window? Why yes, it does, and the spooky store owner absolutely noticed us almost running across the street to check it out.

Outside of arcade hopping (so much pinball!) and scattered shopping, we pinned most of the sightseeing to Sunday: a promised trip up to Washington Park, hitting the International Rose Test Garden, the Portland Japanese Garden, and the Oregon Zoo (and the aforementioned trip to the World Forestry Center).

I'm not sure there's a better cure for what ails a person than a slow walk around the Japanese Garden.

Above all, Portland has kept weird, and strange, and funny, and lovely. It is still one of our favorite places. I hope to get back there soon.