I have spent the past 50 hours in Portland, Oregon, my new favorite city in the country.

I think most people, on every good vacation, get that “man, I’d love to live here!” feeling. It usually goes away in a day or two after the trip is over and real life resumes. Maybe that will be the case with me too, but I’ve never gotten that feeling as strongly anyplace else as I have in Portland. Assuming I’m still doing the same sort of live-anywhere-you-want kind of work in a few years when my kids are out of the house I could quite easily see myself moving to Portland. 

The beer, coffee and food is fantastic. It’s a beautiful city aesthetically speaking. The people are generally pleasant and helpful to obvious tourists like me. The city is nice and compact and walkable and when it’s too far to walk it’s got the best mass transit system I’ve ever used. In the past couple of days I’ve taken the light rail, the streetcar and the bus, all of which has made a big city feel small. I haven’t even been bothered that it’s been unusually hot while I’ve been here.

The “Portlandia” stuff is pretty obvious here, of course. In some ways this is a good thing for someone like me. I’m a pretty liberal guy with progressive social, economic and environmental attitudes and those sorts of sensibilities would fit in here. I could see myself getting somewhat exhausted by it in excess, however. I met a guy for a couple of beers yesterday. He works in public health and he says that the uber-granola tendencies of Portland also lead a lot of people to be anti-vaccinators, to oppose fluoride in the water supply and other similar bits of dangerous nonsense. That might drive me a little nuts, but then again, living in places with stifling conservatism for most of my life already does. I’d be willing to risk the opposite for a few years.

I’ll forego the blow-by-blow of my time here and just offer some observations:

The Ace Hotel: I stayed here. On one level it’s a somewhat ridiculous conceit of a hotel, with its old-timey everything and extraordinarily self-conscious hipster vibe. That notwithstanding, it’s a wonderfully pleasant place to stay. I like the simple, uncluttered aesthetic, wood floors and old plumbing fixtures. And even if it is sort of contrived, it is a legitimately old building – it was the flop house in “Drugstore Cowboy” – and old buildings rule.

Beer: I went to two places, each of which would be the best beer bar in most other cities. Bailey’s Taproom is downtown. Apex Bar is in southeast Portland, but it’s easily accessible via the number 4 bus, which runs often. The selection is fantastic and everything is fresh.

The Heathman: it’s a hotel, but I’m referring to the restaurant. I likely wouldn’t have thought to go there, but my friends in Chicago know their sommelier, James Rahn, and recommended I visit. I ate dinner there Monday night and James sent out drink after tasty drink. Which today has necessitated … 

Coffee. And lots of it. Everyone talks about Stumptown, which is excellent, but the best cup I had was at a place called Case Study. I also had great coffee at a place called Barista. I imagine there’s bad coffee in this city. Luckily I didn’t find it.

Salt & Straw Ice Cream: People from Columbus (and a few other places) are familiar with Jeni’s. This is Portland’s Jeni’s. Or Jeni’s is Columbus’ Salt and Straw. I have no idea. Upshot: crazy-inventive flavors. Including a whole selection at the moment inspired by local food carts. Kimchi. Poutine. Yes, poutine ice cream. I got strawberry/honey/balsamic, though. Really couldn’t bring myself to try poutine ice cream. Especially given that, when I was there, I was still pretty hungover from the night before.

Kenny and Zuke’s Deli is known for their pastrami and other classic Jewish deli fare, but the breakfasts were great too.

And now, a bunch of pictures because I took a bunch of pictures. 

Portland’s train station:


Brace yourself:


This is my room at the Ace Hotel. Yes, that is a giant kitty mural. Yes, that is a turntable. Not-pictured: the very carefully-curated record collection, featuring Iron + Wine and various White Stripes side projects. Because of course it does.

The bed:


The bathroom:


You get the idea.

The Portlandia statue, from which the TV show gets its name. 


My friend Rob told me a weird fact about it: the artist actually has a copyright on it to where it can’t be used on postcards, t-shirts, etc. without paying him a royalty. Even the show pays him to use it in the credits. Which is sort of crazy given that it’s a municipal sculpture at city hall which taxpayers presumably paid for. I had no idea that was done. 

This is Voodoo Donuts, which is apparently a big deal:


I cannot for the life of me figure out why tourists would wait in line in the hot sun on a 90 degree day for donuts. I don’t care how good they are.

The bar at Clyde Common, the restaurant connected to my hotel:


Note: every man in Portland has a beard. I think it’s the law. And I am nowhere near cool enough to go to half of the places in this city.

Light rail. I have no idea why I took a picture of it. I just really, really, really loved being in a city with great transit.


I took the train to Washington Park, west of downtown. It’s a gorgeous, hilly and forested park with a number of attractions. Chief among them the International Rose Test Garden:


From there you get views of the city like this. It was hazy so Mt. Hood is just barely visible to the right of the pic. With the naked eye it was easier to see. It doesn’t look real. 


Like a lot of cities, Portland has some ugly surface parking lots downtown, probably built in the 1970s after some old building was torn down. Unlike a lot of cities, Portland has allowed food stands – basically permanent food trucks – to ring the parking lots:


This little pod of food stands stretched a block or two in each direction with dozens and dozens of options. It seemed like every office worker in the area was eating there. I got a big beans/rice/avocado/cilantro bowl. It was $6 for a 16oz bowl of fresh yumminess that kept me filled all afternoon.

Well, mostly filled. I did have to go get beer:


That’s a Pliny the Elder at Apex Bar. Pliny is a lot like Pappy Van Winkle bourbon, which I wrote about recently. It’s produced in limited amounts and it’s highly sought after and the snob appeal very clearly outpaces its actual quality. But (a) it is still really damn good; (b) I can’t get it in Ohio; and © it’s worth it just to post the pics on social media to make your beer snob friends drool. 

Apex’s taps:


James Rahn at the Heathman:


When a man who looks like this brings you alcohol, you drink it. He knows what the hell he’s doing.

A Portland institution:


Rob told me that it’s the #1 tourist attraction in Portland. I believe it. I bought a book and a tote bag. They gave me a little Oregon car sticker-oval thingie for free. I can’t decide if I should put it on my car or not. It is a Subaru, however, which is clearly the Official Car of Portland, so I probably should.



Matt Groening, the creator of “The Simpsons” is from Portland. Many of his characters are named after streets. In addition to Flanders there’s a Lovejoy and some others. Someone told me that in Northeast Portland people vandalize the signs by putting a “D” after NE” to make “Ned Flanders.” I bet the first guy who thought of that was pretty proud of himself. 



That’s Kenton, the cab driver who took me back to the train station a bit ago. I included him here because he was hilarious and because he rounded down my fare 50 cents from the meter for reasons known only to him. I’ve never had that happen in a taxi before. Like I said, Portland was giving me great vibes.

Oh well, that’s it. I’m back on the train now, rolling out of Portland and heading back east. Back to the working part of this working vacation. Installments when and if cellular service allows.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at Craigcalcaterra.com. He lives in New Albany, Ohio with his wife, two kids, and many cats.

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