Words that have not, to my knowledge, been used to describe me: impulsive, irresponsible, relaxed, goes with the flow (yes, I realize that’s a phrase, not a word), rule-breaker. You get the idea. On that note, let me tell you about the craziest thing I have ever done. I booked a trip to Oregon.

Let me pause while you wrap your mind around such wild and reckless behavior…

Okay, now that you have picked your jaw up off the floor, let me explain. When I was growing up, I rarely got in trouble. I did not even do typical teenager things like break curfew because I DID NOT EVEN HAVE A CURFEW. My parents were so unconcerned that I would actually break a rule that they did not even bother to give me a curfew. I was that teenager.

As an adult, my rule abiding tendencies have generally continued. I get all sweaty and itchy if I even think about doing something wrong or unpredictable. Which is why my recent behavior, you know the whole Oregon thing, is utterly shocking. At least for me.

Rather than fully explain the "wrong" and irresponsible portion of the equation, suffice it to say that I purchased a plane ticket to Oregon approximately 100 hours before I left. All it took was a text from a friend suggesting that I join her on her trip to Oregon and I was headed down a path that will almost certainly lead to desolation and despair. Or, at the very least, to me moving halfway across the country. Which is, according to some members of my family, practically the same thing.

See how excited I am about breaking the rules. Oregon, here I come!

My first stop in Oregon was, where else, Portland. Given that my image of Portland was derived from a strange mix of Grimm and Portlandia, my expectations were high. And Portland did not disappoint. Well, I sadly did not meet any vegetarian werewolves, but I was otherwise not disappointed. Actually, my tour guide had been in an episode of Grimm. But I'm jumping ahead.

Given that it was my first visit to Portland and I just had a few hours to spend, I began my day with the well-known Voodoo Doughnut.

Cliché perhaps, but the peach fritter I ordered was wonderful. Something to know - the selection of doughnuts is, ummm, interesting. Obviously not wanting to take my rebellious behavior too far, I think I must have subconsciously ordered the tamest item on the menu. Oh, and seating is nonexistent inside (although there is a bar where you can stand) so you might end up eating the fried deliciousness sitting outside in the rain. Not that I speak from experience.

Look at that face - only a trip and a really good fritter could make me look that happy while sitting in the rain.

This thing was seriously bigger than my face...

After the all-important combination of sugar and coffee, I was ready for the walking tour I booked with Portland Walking Tours.

Trying to momentarily hide from the rain. Before walking in the rain for two more hours.

The Best of Portland Walking Tour was the perfect way to get an overview of Portland. I even got the full Portland experience when it rained the entire tour. The tour began in Pioneer Square and ended at the waterfront. In between, my guide David provided a fantastic history of the city.

The tour covered the entire history of the city, but especially focused on the transition of Portland from one of the most polluted cities in the US to the model of greenness that it is today.

Portlandia. Apparently it's not just a television show.

This is supposedly the penny that was flipped to name the city. The city could have been named Boston.

My tour guide was in an episode of Grimm, which is filmed entirely in Portland. The bar in the background is where his scenes were filmed, although they ostensibly took place somewhere in Europe.

I can highly recommend Portland Walking Tours. Not only was it a cogent and engaging introduction to the city, at $20 it was a great value. Plus I was able to walk off approximately 2% of the calories I consumed at breakfast. Bonus!

If I'm ever back in Portland, I would love to do another tour with Portland Walking Tours - perhaps one of their food tours. There is even a tour centered on sampling chocolate, which pretty much sounds amazing. Yes, please.

Despite the fact that I thoroughly enjoyed my walking tour of Portland, I was thrilled when my friend picked me up and I could get out of the rain. Desperate for something warm to drink, we quickly found a spot for lunch. Dar Essalam is just south of Portland in Wilsonville. Cozy and absolutely delicious, this Moroccan restaurant was the perfect spot for me to recover from an entire morning spent in the cold and rain.

From there, I enjoyed the ever changing views as we drove south to Medford, Oregon. I knew Oregon would be beautiful, but even then I was surprised by how beautiful. As I considered the possibility of moving to Oregon (which, to be clear, is still just a possibility contingent upon whether or not I can find a job), the mountains were doing a good job of convincing me that I should.

By the time we arrived in Medford, I had pretty much decided that I wanted to live here. But there was one absolutely crucial thing to determine. There is one thing I could (probably) not live without even for mountain views and vineyards (oh yeah, did I mention there are vineyards?!): Mexican food. Lack of decent Mexican food could possibly be a deal breaker. So for dinner that evening, we headed a few miles away to the charming town of Ashland to try Agave Tamales.

I couldn't possibly move somewhere that did not have decent Mexican food...

Not quite my homemade guacamole, but not bad.

One night in Oregon as I ate mouthwatering Mexican food while reflecting on a rainy day and rainbows, I felt the beginnings of a new life in a new place. By no means is that new life a certainty and many things may change in the next few months. But, by taking a chance, by stepping out of my comfort zone and booking a plane ticket, I allowed myself the opportunity to see the possibilities. And those possibilities are really exciting.

That Time I Went to Oregon Part I

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