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Edward Hopper’s Portland?

The Perfect Painter For Dark Days Of The Soul.



You’re not the first Portland baby boomer to wake up on a Sunday with no NFL games that matter.

No early game, no late game, no Football Night In America game.

You’re depressed, but don’t want to admit it’s because of no football. College ball is long gone and the NFL is a week away.

It’s early Sunday, not a bad looking day, but deep in your heart you know it won’t be right for another week, then a long time after that.

Consider Edward Hopper’s famous painting, Nighthawks, and you’ll feel better. Look at Early Sunday Morning and you know what you need to do.

Head downtown and find settings as calm, as fleeting, as hopeless, as Edward Hopper captured on canvas.

Take a partner, an assistant with a keen eye, in case you miss something.

The first stop was accidental. You know how it is when you look for one thing and find another?

This is what I stopped for. (Take I-5 north to Front Avenue exit and make the right at the light that leads toward the Riverfront Athletic Club.)

The white one is the former First Interstate Tower that city leaders promised would never happen again. The other is the KOIN Center that once built forever blocks the Mt. Hood view coming out of the Hwy 26 tunnel.


It’s a little too big for Edward Hopper to paint, and the attitude isn’t down enough, but it’s still got a nice patina of sadness.

Before I jumped back in the car I turned around and saw this. It felt like Hopper Vision right here in Portland.


The stark contrast. The sharp diagonal shadow. All that’s missing are morose people ignoring each other or looking out a window.

A leafless tree landscape and Soviet bloc looking architecture felt morose enough. When light rail rolled into the frame, I felt certain one sad passenger had to be looking out the window for a Hopper moment.


I stayed off Harbor Drive to Front Ave and paralleled it to the turn around in front of the River Place Hotel for a view of the Hawthorne Bridge.

Along with a nice bridge view I saw something Thomas Eakins would like to capture. Since Eakins is one of Hopper’s favorite painters it was a score.


Head back to Harbor Drive and take a right on Front Avenue. Waterfront Park sits on the right as a testament  to Portland’s urban planning. Instead of commerce right to the water’s edge, we have a huge open space.

Follow this celebration of greenery north past the Burnside Bridge. Stay left or you’ll end up crossing the Steel Bridge headed for the Moda Center / Rose Garden on the east side.

Aim for the Fremont Bridge and get ready for monumental size. You get that with a double decker over the Willamette River.


This may not have the Hopper feel right away, but on the other side of the river and to the left is a scene that hasn’t changed in a hundred years. In other words, Hopper-land.

Early Portland started with camper / explorers. No one showed up with a room booked in the Heathman. They packed their gear in and back out.

As the city grew, business reached out into the river on pilings and docks. It’s beautiful in it’s own special, undisturbed way.

From a distance it looks normal.


Closer up it looks like an abandoned waterfront on another city time passed by.

But this is Portland. How can this happen? Maybe it’s a tribute to Edward Hopper, or the next Hopper.

With the boats on the water it may turn into a Hopper / Eakins collaboration.


Fans of industrial ruins don’t need to book a flight to Detroit. Front Ave’s north end has all you’ll need, and then some.


A big surprise on Front was the swarm of birds, all alike, flying from a red berry tree, to a resting roost, and back.

They flew like they’d never seen a human before, buzzing my head in perfect Alfred Hitchcock creepiness. If you haven’t seen The Birds, don’t worry. These birds didn’t seem intent on pecking an eye out.

What are they called?


After some birder research, they look like Cedar Waxwings.

You can’t be certain without a closer look?



The next time you look out on the day and wonder, “Why bother,” get outside and surprise yourself.

Our man Edward Hopper laid the groundwork for identifying a certain phase of life. Sometimes his work looks like the Boomer Phase. We’re tired and worn out just like Hoppers people, but we’re Oregonians. We have Portland, not New York City.

We have resources. Whether trapped by the blues, or celebrating life with hands raised high, find an artist who speaks to you and find their inspirations in your neighborhood.

That’s a boomer thing. Love to see what you find. If you get questioned, tell them Boomerpdx sent you on a mission.



About David Gillaspie


  1. ‘The next time you look out on the day and wonder, “Why bother,” get outside and surprise yourself.’

    Well said. I’m-a gonna tweet this, it’s so good 😉

    • David Gillaspie says:

      It’s not for everybody, but ought to be. So far the artist in the neighborhood idea is gaining traction. Edward Hopper got me the first time I saw a reflection in a Horn and Hardart cafeteria in Philadelphia. Everyone looked less than thrilled to be there. Such a Hopper moment with a tuna salad from who knows how long ago sitting on a plate, daring to be eaten.

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