A Hitchhiking Failure, Craigslist Success, & Portland’s Welcoming Rainbow


What a city. So creative, so historic, and so wonderfully weird. And I wouldn’t have it any other way.

After exploring Seattle to my satisfaction, I was very excited to continue my epic West Coast Journey by returning to Portland before I headed further south. If you’ve been reading Byteful Travel for a while, you already know that I’d been there briefly before I headed up to Seattle. And while in Portland, a unique opportunity presented itself: I met someone interested in hitching up to Seattle. After walking over a mile to a promising ramp, we caught a ride in about an hour.

Now I could either give you the “director’s cut” of the story, or I could share some of the gory details with you, like the bit about how my first attempt to get out of Seattle didn’t work… at all.

I’m going to do the latter here; because I want to emphasize the importance of having a Plan B and being flexible. And if it isn’t already abundantly clear from past articles, setbacks happen all the time; and that’s one of the reasons it is so sublimely helpful to release your attachment to specific outcomes as much as you possibly can. But that’s a pretty hefty topic in itself and deserves its own article.

Entering the Sweet Spot of Suck

Now it just so happened that my last Couchsurfing host in Seattle (who became a friend in the process) was an avid hitchhiker. In fact, he’s an amazing person overall, and he encouraged me to depart from Seattle the same way I’d arrived, through hitchhiking. That morning he even bought me breakfast (a gesture that will never be forgotten), and helped me pick out a good intersection to hitch from. But when I arrived at the intersection, something was off.

The intersection was somewhat of an onramp to the highway (which is what you want when hitchhiking), but something didn’t feel right. No one would stop for me at that location, despite my crafty little sign (a technique that had worked very well for me before).

Now, to be fair, I’d screwed up a bit even before I got to my spot. I’d gotten there rather late for hitching out of a large city. It was around noon by then, and most traffic leaving the city leaves earlier than that. Since I didn’t have a time machine, I decided to take a bus further out of the city, found a new ramp, and even got two rides in succession. But then I got stuck. I’d made it past most of Seattle’s suburbs, but not even remotely near Olympia. I was far enough out of Seattle that most traffic was going the way I wanted, but I wasn’t near an area that had enough traffic entering the freeway.

I had entered the sweet spot of suck.

The Failed Hitchhike that Resulted in… Singing?

To escape the sweet spot of suck, I ended up catching what I found out was the very last bus back to Seattle. I returned back to my friend’s apartment and told him the story. He sympathized, and I started formulating a backup plan.

I could have tried again the next day at an earlier time, but I was feeling rather burnt out from hitchhiking. Had I known what I know now, I might have looked into taking a train from Seattle to Portland; but 2009 was the Dawn of Leveraging Craigslist in my life, so I started by looking there. About a day or two later, I’d found a ride going directly to Portland. I called the number up and it turned out the driver was a rather hip old lady. I met her the next day, and talked with her. I got a very good vibe from her, so I joined her in her journey back the eternally weird city that is Portland.

On the way down to Portland, she told me she needed to stop at the hospital to do her job which was to entertain some of the older patients. I asked her if I might come in and listen. After checking with the hospital, I was allowed to come in and help her, which turned out to be a lot more fun than I would have guessed!

For about an hour, she played guitar, and we sang to disabled people in the hospital. She played some very old folk songs that I hadn’t heard since I was very small, and we had a blast all singing along. Not all of the patients would sing, but I could tell that those who did really enjoyed themselves. The whole experience was an unexpected delight on my journey and a great example of the happy accidents that come to you while travelling.

The Second Rainbow of my Journey

The drive down to Portland was super smooth, and the weather was just about perfect. I had her drop me off next to one of the parks near my Couchsurfing hosts. After paying my share of the (relatively small) gas expense and thanking her, I crossed the street and decided to relax in the park for a moment.

The very moment I entered the park, I looked up and saw a stunning rainbow hovering just a few meters above the ground. Small water droplets from the park’s fountains were creating this rainbow much closer to the ground than a naturally occurring one, but it was a rainbow nonetheless. I had to capture this moment.

I struggled to get my camera out of my pack in time to capture this, the second rainbow of my journey. I pulled the camera out, held the power button down, and yelled at the camera as it had the nerve to take an entire second to turn on. This single second felt like an eternity.

The Rainbow under the Park Fountains

After an eternity, the camera was ready; and as fast as scientifically possible, I aimed and fired. Just a fraction of a second later, the timed fountains turned off and the rainbow vanished.

But I’d snapped the picture in time. I’d captured my 2nd rainbow, and I was so grateful. I almost felt as if Portland itself was welcoming me back through this rainbow appearing to me at the perfect time.

Portland was Quite a Hotspot, Literally.

So excited I was to have returned to Portland — to finally have the chance to explore it in depth. What I didn’t yet realize was that I’d returned at the very beginning of what turned out to be the hottest week of the year.

But sometimes that’s how things work out, so I rolled with it. And while my first few days back in Portland weren’t the most productive days of the journey, I did have fun spending time with my Couchsurfing hosts’ kids, making icy smoothies and going to the park at lunchtime. The temperature easily reached over 100°F with considerable humidity in the air…

So it was basically like Mexico all over again. Good times.

Thankfully, we lived through the sweat-bomb that was the final week of July; and once the risk of bicycle-induced heatstroke became minimal once again, I finally set out and started exploring Portland in greater detail. Best of all, a friend of my hosts (who was also a Couchsurfing member) offered to take me on a bit of a walking tour around Portland. I’d talked to him before, and I knew he was a really smart guy. Turned out he was very knowledgeable about the city, and I jumped at the opportunity. The timing worked out very well, and I felt so lucky and grateful for what was to come.

Rainbow as a Metaphor

Remember, if my attempt to hitchhike down to Portland hadn’t failed, I never would have seen the 2nd rainbow of my journey.

If you’re currently experiencing difficulties or obstacles in your own life, take heart. For without the storm, a beautiful rainbow could never appear!

Next time:
A remarkable walking tour that changed my perception of Portland forever.

Remember Marco?

And, while you anticipate the story to come, why not see if you can find Marco in the photos in the album included with this article? (Yes, he continued to follow me.) And remember, since his suit is usually solid white, he tends to hide in the bright areas in the photos.

For those of you recently tuning in, on this entire trip I was being followed by a very peculiar (and very small) spaceman from another world whose name is Marco. If you’re new to the “Where’s Marco” game, it’s like “Where’s Waldo” or “I Spy”. For tips on how to find him, read this first.

Do you have what it takes?
Checkout the Portland Walking Tour photo album and find Marco! →

And Now

Continue the Journey →

All photos from this event are in the Portland Walking Tour album. All photos in the Gallery can be used as desktop wallpapers because they are high resolution (1920×1440).

3 bits on A Hitchhiking Failure, Craigslist Success, & Portland’s Welcoming Rainbow

  1. Pingback Carnival of Cities for 23 March 2011 | Sheila's Guide To The Good Stuff
  2. I’ll be in Portland and Seattle in just over a week – can’t wait! Maybe I will see a rainbow too? 🙂

  3. Aloha Andrea!

    Thanks for stopping by. If you see a rainbow, totally let me know. That place seems to be full of rainbows. 🙂