May 26, 2024

The Trekking Tailgater: Portland, Oregon

I’m here to tell you some stories of the things I have encountered on the road. Some of them are just really cool, like a herd of 500+ Elk in Montana (not this article), or just some good old fashioned debauchery I got myself into (this article). With a nod to Sophia Petrillo from Golden Girls…

Picture it, Portland Oregon 2015…

This was my very first trip to Portland, smack in the middle of a week that took me from the Canadian Border all the way down I-5 to San Francisco, visiting clients along the way. Of course, being my first time in Portland, I wanted to stay downtown and explore a bit in my free time. Luckily, or maybe unluckily for my liver, a client needed to push their appointment back a day so instead of one night in Portland I now had two.

It was winter, so hotel prices in downtown Portland were reasonable. I was able to book a newly remodeled hotel in downtown named, The Sentinel, for $120 a night. I have looked many times since then and never found a price less than $250. However, if you are treating yourself, and that doesn’t bother you, I would recommend this hotel. Evening rolls around and it is time to go find something to eat.

If you have been to Portland, or even read about it, you have probably heard about their food carts downtown. I did not go there because I got distracted. Walking down the street, just looking up and down the cross streets at marquees I spotted a beacon in the night. A green neon sign calling out to me that read Cooter’s. Being a little demented, and a huge fan of Duke’s of Hazard as a kid, I decided to find out what kind of Cooter’s we were talking about here. So, I turned the corner and headed that direction.

The sign was probably three blocks away from when I turned the corner, and as I got closer I realized that it was not Cooter’s at all but Scooter’s. You see the S had been hiding behind a light pole. Crushed, I soldiered on because hey, I was almost there anyway and their seemed to be some commotion outside on the sidewalk.

Turns out that Scooter’s is a bar. A 100% proper dive bar no less. Suddenly my spirits were picked up because I love a good dive bar, so in I went. I sat down at the bar next to a man in a trench coat and a ponytail. Think Adrian Paul from The Highlander, but a bit heavier. I order a bourbon and water. A fair selection of bourbon is on the wall but I go with Buffalo Trace. The bartender makes my drink as I am looking around the bar taking in the decorations. I turn back to the drink as he puts it down and it is a pint glass, and while the glass was clear the liquid was BROWN. Immediately I knew I was going to like this place.

A bit later, I strike up a conversation with The Highlander (real name Dave, but after introductions I never called him Dave again). By drink two or three the whole bar is calling him The Highlander and these are people he knows well that had never put that together. I wonder if he still gets called that? Moving on. He asks me the usual stuff: Have you ever been here before? Why are you here? etc. After a while he says he is going to go out and smoke. At the time I was still a smoker so I joined him. (Quit cold turkey 6/29/18, yay me!)

Remember that commotion outside I mentioned earlier. Turns out it was a line to a concert around the corner. The Highlander, flabbergasted that I had never heard of the Crystal Ballroom, explains what that is to me. If you are a big music person, you probably know it. If you’re like me, probably not. We begin talking to a few of the people in line, and it is a concert for Patti Smith. Ms. Smith may be most notable for “Because the Night”, but was a big part of the punk rock ’70s era. The Highlander and I go back inside.

Three or four drinks later, The Highlander remembers that I have never been to the Crystal Ballroom and picks up his phone. Five minutes later, a dude in a headset walks into the bar with two wristbands. “Put these on they will get you into the show.” Apparently in his hundreds of years on the earth The Highlander has made some connections. Off to the show we go. After about an hour we’ve seen the highlights and Patti’s getting a little preachy on stage, so we bounce. Great show, fantastic energy. Would totally recommend seeing her if that’s your thing.

Back at the bar I decide I should probably get back to the hotel as I need to be coherent the next day. I am figuring I have at least a $100 bar tab by now since I’ve had 7 or 8 bourbon and waters and bought a few of The Highlanders drinks as well. I could not have been more wrong. The drinks, and two Chili dogs ($1.50 of delight), were a grand total of $42 dollars.

I thought there had to be a mistake, but The Highlander assured me there was not, Scooter’s is just cheap because it’s a bar for locals. A healthy tip later and some “see you tomorrows” to my new friends (2-night stop, remember?) and I’m out the door for the hotel.

Back at the hotel there is a bouncer standing outside the door of the bar inside the hotel (Jackknife). Ever the salesman, I ask him what is going on. Whiskey distributor’s whiskey tasting event for bar owners. (all free!)

Using some salesman skills and the fact that in a roundabout way I’m in that industry, I talk my way in. The night gets a little fuzzy at this point, so I am going to cut the story off with this. I drank ALL THE BOURBON. As they shut down the tasting I stumble up to my room for a much shorter night’s sleep than I had anticipated leaving Scooter’s.

I don’t know if there is a moral to this story, but it was a darn good time. Take advantage when you can of the places you travel to and explore. It may not always be debauchery like this story, but you may stumble across something cool like those Elk I mentioned.

See you on the trail.

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Aaron Wall 28 Articles
Aaron is an Iowa State graduate in Exercise and Sports Science. A published poet and once told by the dean of Iowa State's Liberal Arts college to pursue creative writing, he is still probably the least qualified contributor at The Tailgate Society. With less than 100 followers on twitter and no insta, snap, or tick tock you can probably guess that he is ancient. Also a certified curmudgeon by his wife.

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