A bit of Portland

The customs officer studied my passport.

“Where are you going?”

“Portland” I answered.

“Have you been there before?”

“Nope, first time.”

“Are you bringing brass knuckles?”

“Um .. no. Do I need them?”

I’m not certain it’s legal to bring brass knuckles in my carry-on, but apparently it is advisable if you’re staying in downtown Portland.


I had high expectations as I planned my work trip to Portland. I thought of it as a small Vancouver — mountains, craft beer, trendy restaurants and trendy people. The customs officer’s remarks were the first indication that I might be setting my sights too high.

Not that Vancouver doesn’t have problems. You only have to walk two blocks past Gastown to get a sense of the addiction problems that plague parts of Vancouver. There are large tent communities of homeless people in Vancouver, one of the most expensive cities in the world to live. Yet, walking through downtown Vancouver, you don’t see any of that. Not much of it anyhow.

Portland is very different. Homelessness is stark. There are tents pitched on sidewalks and along streets everywhere you go. Alongside freeways, on residential streets, on commercial streets … everywhere.

I’m used to seeing tents. I see them in Winnipeg, as do you I’m sure, but it’s nothing like in Portland.

However, at no point did I feel as though I needed brass knuckles. The tents were tidy. The occupants, largely unseen or unnoticed. You get the sense that this is just a place very down on it’s luck.

Portland was hit hard by COVID restrictions over the past couple years. The riots that followed the murder of George Floyd kicked Portland while it was down, and the scars of both are still visible.

Businesses all over the city shut their doors and boarded their windows — many for the long term. High-end stores and uptown pubs have painted plywood on their windows, waiting for a day that fortunes improve.

Although I may have felt safe, crime is an issue as well: Portland has a higher than average crime rate — safer than only 3% of American cities according to one website. Portland, a city the size of Winnipeg, has about double the homicide rate. In the particular area of downtown I was staying in, there were 6 homicides and 843 assaults in the past year.

So there is some work to do to restore the city on the Columbia River to it’s former glory. Much of that work falls on local governments. In addition to the pandemic and the riots, Forbes puts the blame on “past policy to restrict housing … combined with lack of civic leadership” in their story Death Of A City: The Portland Story? “Portland has shot itself in the foot” they say.

I don’t mean to paint an overly negative picture. Portland has a lot going for it. Even just getting a short three-day glimpse of the city, you get a feel of the community spirit. People are skooting around on their electric scooters and skateboards. They’re hanging out at street dance parties. They are going out for dinners and going about their business.

There is still some nice architecture around town, there appears to be a good local transit system and it has great natural advantages including a moderate climate and scenic surroundings. Urbanists might not like the proliferation of one-way streets and dearth of proper cycling infrastructure, but I found the downtown area at least to be very walkable.

Again, this is just a snapshot. I don’t know the city well by any means, but it’s information to get a look at other city’s struggles and successes when one is evaluating their own city, as we’re all doing here in Winnipeg in the lead-up to the fall civic election.

Would I go back? I’m not in a hurry to, but I wouldn’t hesitate to either if there was a reason for it. In fact, I would be curious to return in five years to see how things have changed. Besides, there is still good food to be found. And of course, craft beer.

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