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Stop 11: Portlandia – The Land of Rain

Portland basically told me, “f*** your feelings.”

When one door closes another one opens. In my case, these doors are whirlwinds. After the craziness of the conference I mentioned in October and Sydney’s visit, I had a wedding-palooza with 3 rescheduled COVID weddings in 8 days. After wedding-palooza, I stayed in San Francisco for a week to orchestrate my Dad’s (COVID-protocol following) 79th birthday party. Needless to say, after all 3 of these things, my body was completely gassed by the time I got to Portland.

Like Seattle, Portland has never piqued my interest as a top spot to move because of the rainy weather. More on that below. At this point of the trip, I could definitely feel myself running out of gas. As a perpetual creature of habit and homebody, I’m surprised I lasted this long. That said, I’m definitely glad I made the decision to close with the West Coast.

Even with its own specific Portland Personality, there’s still something much more familiar in the chillness and slow pace of Portland than in other parts of the country. I’ve only been to Oregon once as a kid when my sister ran on a national track team but I’ve heard great things over the years from my friends so it made sense to see what all the hype was about.

The Good

Transit/Walkability. I do a fair (but not exhaustive) amount of research on each city when I’m en route or the first night I arrive. One of the top repeated comments was that even though Portland is a city, it feels more like a small town. After a couple of days, it became abundantly clear why that was the case. The city’s public transit system is pretty top-notch in certain areas and makes it really easy to move around the city. On top of that, they have a car-sharing service called Free2Move that is like Zipcar and Getaround but with two primary exceptions: 1. The cars are all Jeeps (Compass or Renegade) and 2. You can drop them off within a designated boundary that covers the majority of the city. Game changer!

Donuts. Voodoo Donuts gets a lot of the love and attention here and while I did go to the original location, I can’t say it was my favorite. Blue Star Donuts was another franchise that was high on the list but sadly, I didn’t make it there. Where I did make it, however, was Pip’s Original Donuts and Chai. It was a bit out of the way from where I was staying and the wait was easily over 30 minutes but OMFG, it was beyond worth it. I’ve never inhaled donuts like that before and the chai was pretty damn good too. I highly recommend making a stop here.

Nature. Portland and the state of Oregon as a whole have some phenomenal nature to boast. The fall colors were still in full effect despite the city having absolutely zero interest in clearing the leaves, ever. I took the time to drive to Bend to see an old work colleague and the route was simply breathtaking. One minute it’s all trees and the next it looks like I’m in some prehistoric Jurassic zone. I hear in the summer months all of the rain pays off and nature is bursting from the seams. Speaking of which…

The Bad

Rain rain and more rain. As I said in Seattle, I hate rain. Portland basically told me, “f*** your feelings.” It rained every single day I was there except for three. From a sprinkle to a heavy downpour, I’ve never seen rain quite like that. It was 37 degrees one night. Excuse me….can I speak to the manager of Portland? At some point, I suppose I acclimated to the PNW way of distinguishing between rain that’s acceptable to go out in and rain that isn’t. Either way, not for me.

Holiday crunch. Even though the rain severely zapped my mood after my energy had been drained, as stated at the top of the article, I still wish that I could’ve had more time. With the first week of the month spent at home and the last week getting eaten by Thanksgiving and a subsequent work retreat, I only had about two and a half weeks to explore. When putting together this itinerary, I’d always known that this would be the case, but it still sucks.

Being Queer in Portland

Portland is another very queer city so it didn’t feel worrisome in the slightest. Unfortunately, Portland no longer has a formal gayborhood and I didn’t get a chance to lean into the queer scene as much as I would’ve hoped. The sense I get though is that it’s a small community and everyone either knows or has dated everyone.

Being Black in Portland

It dawned on me that the last three months have been in three mega-white cities: Denver, Seattle, and now Portland. I honestly don’t know who wins out between Oregon and Colorado but goddammit, it’s really fucking close. I wasn’t necessarily made to feel “other” as I have in other places but I also did not come across a lot of people that looked like me.

Final Thoughts

It was a short but sweet time and despite the rain, I was able to find enjoyment. I even had the chance to go to the last Blockbuster on Earth in Bend. One of the things I love about Portland is the immense neighborhood and city pride. It’s apparent in anyone I came in contact with or casually encountered. It’s an amazing breath of fresh air compared to other cities on the tour this year.

Will I be back?

Absolutely. There’s so much more to see and do. I also want to see it in the summer when the sun is endless. 

Could I see myself living there?

No. This is an easy one. Aside from the rain, the city just feels too small for me. I could see myself growing bored of things after a few months. That said, I’m sure that works for a lot of people but I need a little bit more, either in the city size itself or cities that are within an hour’s drive to help diversify the activities and adventure.

City Ranking

1. St. Petersburg, FL

2. Playa del Carmen, MX

3. New York, NY

4. Seattle, WA

5. Portland, OR

6. Charlotte, NC

(Philadelphia, PA)

7. Chicago, IL

8. Denver, CO

9. Atlanta, GA 

10. Washington, DC

11. Austin, TX

(Nashville, TN)

Portland, OR

Next City

San Diego, CA….final stop!


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