Road Trip To Portland Oregon



Three homeless fill the doorways adjacent to the police station – Portland Oregon

I was less than an hour into my drive from Portland Oregon back home to Bellingham Washington when I pulled off for gas. I was accelerating up the entrance ramp to rejoin I-5 when I noticed a figure standing on the side of the road. The only thing I could see clearly was the guitar case. I pulled over and the figure opened the door.

“How far are you going?” he asked.

“To Bellingham.” I replied.

“Great! I’m headed to Seattle.”

The figure opened the rear passenger door and slid his wet backpack and guitar case onto the deck, slammed the door then climbed into the front seat. T-shirts, a dark sweatshirt and a fleece collar erupted from the unzipped portion of his coat, just below his chin. His coat was once a bright blue and white parka but now it was a dingy blue/grey, the waterproofing was worn down to an ineffective dull finish and the flashy white accents had a patina of mud stains. A black wool cap hid his hair and a greying goatee his chin. The thick slabs of glass in his Buddy Holly-like frames magnified his eyes to an eerie level; like those of an insect on display.


Homeless camp outside the Amtrak Station – Portland Oregon

This weekend I spent a lot of time around the homeless; I stayed two nights at a hostel in downtown Portland and explored the area on foot. I’ve been visiting Portland regularly for over thirty years and I lived there in the eighties and nineties. Old Town Portland has been known as a gathering place for drunks, addicts, prostitutes and the mentally ill for as long as I can remember. But the volume of people sleeping on the streets far exceeded anything I had seen before in Portland. On every street I walked I found someone wrapped in blankets and lying in doorways like the morning paper or clutching grocery carts filled with everything they owned. After wandering around Old Town for a few hours I decided I needed a change of environment. I walked to the other side of the city, past Nordstrom’s and the fancy hotels to the history museum and Hot Lips pizza. But no matter where I walked I could always see at least one homeless person in my field of view. Some of them asked me for money, some eyed me seductively and smiled, others engaged in arguments with imaginary foes and two just stared at me then began yelling.


Gate to China Town adjacent to “Right to Dream Too” homeless tent camp – Portland Oregon

I returned to my hostel by way of China Town. Next to the Chinatown arch is a homeless tent-camp known as “Right to Dream too”. A volunteer at the gate asked me about my camera. It turned out he was a visiting photographer from Paris. I asked him, “How does this camp work?”


“Right to Dream Too” homeless tent camp at entrance to China Town – Portland Oregon

“Homeless can sleep here uninterrupted for twelve hours. We have a woman’s tent, men’s tent and a couple’s tent. We give them bag lunches, blankets and other things.”


Homeless man – Portland Oregon

More than two hundred people sleep there everyday but they never have enough room for everyone. It is believed that there are around two thousand homeless on the streets of Portland and sixteen thousand in the county. Getting a precise count is impossible but the population regularly rises during the warmer months, when the younger homeless return to Portland.


On the other side of the window at Powell’s Books on SE Hawthorne, Portland Oregon

“It must be difficult to keep the peace with all the personalities.” I said.

“Yes, it is. Sometimes we have to call the police.”

“It sure is!” commented a homeless man standing next to me. “I nearly got into a fight with a guy over a blanket last time I was in there. But the staff intervened and cooled things down. They did a good job.”

The homeless man’s drooping eyelids, white hair and gravely voice made him look and sound like Nick Nolte from “A Walk In The Woods”.

“Excuse me”, he said, “but do you have bus passes or backpacks?”

The volunteer replied, “No, we don’t have any backpacks but the mission has bus passes.”

“Have you been living on the street long?” I asked the gravely voiced man.

“I did a long time ago. I never thought I would be back here again. A lot of these people fall on the street and can’t pick themselves up. I’m blessed, I can. It’s hard, you don’t have a rental history, job history, can’t get an ID. They count your arrest record against you.”

“You can get a backpack at the mission if you have a medical slip”, the volunteer added.

“Geez!” the homeless man gasped. “I feel like going to the library and printing out some fake medical documents to get a backpack.”

He turned and began to walk away. “Good luck”, I said.

“You too, man”, he growled.


On the hostel’s roof top patio looking east across the Willamette River. Portland Oregon



Lobby of “The High Society” hotel/hostel on 3rd street in Old Town, Portland Oregon

By early Sunday morning I had my fill of Portland, homelessness and sadness and started driving back to Bellingham before dawn. But now, less than an hour later I’m sitting next to a homeless man. He had a cough but that didn’t prevent him from talking nonstop all the way to Seattle.

“I was down in Eugene visiting my son. I decided to hitch to Seattle. Why pay for something when you can get it for free?”

He had spent a few nights in downtown Portland over the years and told me what he liked about the city and the state.

“The Burnside free clinic is the best. I tell all my friends to go there. Oregon’s great. Oregon’s the only state I know where you can hitchhike and never get hassled. You can’t do that in Washington or Idaho. That’s why I was standing in front of the highway sign when you picked me up. They can’t arrest you in Washington for hitchhiking on the interstate if you’re standing in front of the entrance sign.”

“Which police pick you up, state troopers or locals?”

“Oh, it’s always the local police, but they don’t arrest you. Like in Idaho, they just drop you off in the next town. They just don’t want you hanging around their town.”

“But this is great, I’ll get to Seattle in time to watch some of the game and still play the market. I’m a street musician. I play at Pike Street Market, a hundred bucks a day. I couldn’t make that kind of money in a regular job, paying taxes and insurance.”

“That’s pretty good, a hundred bucks cash”, I said.

“Oh, that’s nothing. The girl that sings near me pulls in two hundred a day. But I usually go to Sundance Utah in the winter and play the streets there. The last two summers I spent in New York City. I played for Miley Cyrus. She liked my playing too. She didn’t give me any money but she looked at me and smiled as she walked by. She was wearing a black dress and carrying her guitar.”

“I also played for Alec Baldwin. Oh that was funny. He and his pregnant wife came up, she is so beautiful, she stopped and was listening to me play. Then he saw all these photographers and started to get real nervous, but they weren’t Paparazzi, they were students in a film class.

He grabbed her and said, “Let’s go!”

But she said, “No, I want to listen to the music.”

It was so funny. But I have yet to get my “celebrity tip”, you know a hundred dollars or something like that.”

As my guest warmed and dried the car took on the smell of a locker room and he continued to share his wisdom of the road.

“It’s the food that matters. The mission in Seattle does it right, they feed you good. We have Bill Gaits to thank for that… If you want to get picked up you got to look dry. No one wants to pick up a drowned rat. I go into McDonald’s or Starbucks to dry off before I start hitching and I keep my shoes shined.”

He lifted his right foot and placed it on his knee. His boot had a shine so bright and glossy black that it could easily pass a military inspection.

“My dad taught me that. He said always keep your shoes shined.”

In Seattle I turned off I-5 onto Olive Street and let the street singer out. He thanked me for the ride and I wished him well.


The library at Reed College. I was never a student at Reed but I spent a lot of time studying in their library. Portland Oregon

It was an interesting couple of days in the big city but I was ready to get back to little Bellingham. Bellingham has homeless too, but you don’t see them sleeping in doorways on every street. In fact the homeless population has decreased by thirty-five percent since 2008 and most of those on the streets of Bellingham lived in local homes before they landed on the street. Portland in contrast seemed to be a destination city for homeless and their presence has significantly altered the look and feel of the city in recent years.

I did have a good time visiting my old Portland haunts like Powell’s Books, the Reed campus and SE Hawthorne Street. Bars, coffee shops and bike shops were many but its that way in lots of cities, the homeless, that’s what stood out on this visit to Portland.


Cuban restaurant in SE Portland, Oregon



Categories: Travel, Writing

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16 replies

  1. Looks very enjoyable! Portland must be quite fascinating. It’s actually one of the few US cities I haven’t been to. Looks like I have to rather sooner than later!

  2. It is true that Portland is a destination city for many homeless. The pleasant summers and relatively mild winters have something to do with that. However, the levels of homelessness have never before approached current levels, at least not in our lifetime.

    My daughter is a social worker in Portland. She told me she is studying computer programming in her spare time because social workers typically burn out in five to ten years, depending on their specific duties, and she is already anticipating her pending burnout. – Mike

  3. Great post, Brick. Interesting exchange you had with your hitchhiker, and lovely photos. I have been only once to Portland long ago, would like to return, espec. to go to Powell’s Books. It is sad to see so many homeless there, but the camp is a terrific idea. Thanks for sharing your Portland adventure with us…. 🙂

  4. Nice of you to give him a ride. That’s a hard life.

  5. Nice to get a dose of good old Portland. I’ve been away now for longer than at any time since the early 90s. I didn’t know you lived there. I miss it, but not the rain they’ve been getting.

  6. I read your interesting blog about being in Portland in Dec. 2015. The homeless issue is not getting any better that I know of. Being an older person born and raised in Portland, I’ve seen many changes over the years, some for the good and some not. I won’t go into my feeling about the homeless, but something needs to be done and soon. Portland was in the news for several years about it’s great living conditions and now it is again, but now about its high cost of housing and our homeless issues. Maybe a new Mayor will be a help, I hope so! I must admit I do not live in The City any longer, moved to the burbs years ago.

    • Thanks for the comment, Don. I lived in NE and near OHSU during the 80’s and 90’s. More recently I stayed at hotels near the airport, this was the first time I slept downtown. I couldn’t believe how much the city had changed. Walking around Chinatown, Old Town or even Pioneer Square after dark gets a little crazy, even without riots. I was stepping around bodies and had to jay walk more than once to avoid a fight between street people on the sidewalk ahead of me. I’ve always liked Portland but it’s quality of life seems to have fallen a fair bit over the last decade or so. I hope it bounces back soon.

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