Why I Didn’t Love Trendy Portland, USA

You know how there are those places you’re really excited to see, then you start worrying whether your high expectations will be dashed?

You know how sometimes you needn’t have worried at all, and the place was, as you first imagined, amazing?

Yeah. Portland wasn’t that place.


To be honest, it hadn’t even crossed my mind that I might be thinking too highly of Portland. It’s had a lot of hype recently: the rising hipster, cool place that is full of people who love coffee, books, quirky bars. And on top of that, it’s surrounded by some pretty awesome nature. What could I not love about this place (um, despite actually not loving coffee myself)?

Well, it turns out that soon after we stepped off the Amtrak and onto the train platform, post-hell-of-a-journey-where-everything-went-wrong (more on that in a later post), my first impressions weren’t the best.

So, why?

In all the hype about Portland, I expected it to be lively and have lots of different vibes. I read up on the Pearl District, where we stayed – supposedly a trendy place – but found it largely empty. There was a pub here and there, a restaurant dotted around… but… where was everyone? I put this down to it being relatively late in the evening. But… it was a Friday. Ok, so maybe we weren’t in the right area of the Pearl District. That must be it. The plan was to sleep after our big day and tackle a new part tomorrow. Things will pick up then. I would love Portland.

Our first moves were to go to Voodoo Doughnuts, Powell’s Book Store and Stumptown Coffee (all of which I did like). As we walked, I kept waiting for a bit more of a scene of people… it didn’t happen until we got to Voodoo Doughnuts: seeing the line, I joked to Alan that this is where everyone in Portland is.



What I came to discover is that Portland, even though it is a city, doesn’t behave like a city. It has a very small town feel to it, the streets are wide and everything’s quite spread out. Alan didn’t find this so hard to get his head around which confused me until he pointed out that I’m from London. It’s a good point: London is big too, sure, but it’s high with its skyscrapers and compact. You rarely walk a street that doesn’t contribute to one of the many characters that make up London. Whether it’s Shoreditch, Greenwich, Chelsea, Peckham, Covent Garden, Soho, or anything else, you can walk almost seamlessly from each city vibe.

Portland doesn’t really have this, or at least not from my point of view. Each place we walked, you’d pass quite a few blocks where nothing was going on. And I mean nothing… I like walking past resedential areas, but they’re not what these barren blocks consisted of. They looked industrial and incomplete, and the sparsity of places bothered me. There would be a pub, and then nothing… a coffee shop, and then nothing… sometimes there would be a cute line of shops/bars/cafes, as if you had to work for the treat.

I think my expectations weren’t on the same wavelength as what Portland is really like. If I had spent more time there, I probably would have sniffed out the best parts and worked out the vibe. Problem is, the city doesn’t seem to cater for someone who is casually walking around; it seems like you have to know where you’re headed – those were the times when Alan and I had success and liked what we saw.


A bare building made better with street art

I would still go back to Portland if I was in the area – but I don’t think I’d make a specific trip there. When we left, I felt my head hang a little low: I wasn’t disappointed in Portland, per say, but more disappointed in myself that I had projected a view of Portland – and obviously the wrong one – which made me have to grapple with my own mind to understand it. It was as though I was working backwards to get to the ‘start from scratch, clean slate’ I should have started with.

But then again, that’s all part of travel, isn’t it? Your experiences in life determine what you think and how you perceive things – growing up a Londoner has impacts on me I’m still finding today, apparently. And it shows you that the simplest of things can throw you off: I’ve adjusted fine and embraced differences in all sorts of places, but Portland was like missing a step on a staircase.

Maybe I’ll work you out next time, Portland.


P.s. No word of a lie, the bracelet I bought at a Portland market broke and fell off during writing this. Talk about payback.


  • Good to know if I make my way to Portland one day. Thanks!

  • I haven’t been to Portland, but I’ve felt like this with a few American cities I’ve visited in the Midwest and on the West Coast. Your description of ‘a pub here and a restaurant there,’ and empty blocks, fits my experiences! Maybe it’s because we’re used to ‘walkable’ cities in the UK and Europe? Plus, London is a tough one to beat :)

    • Maybe so! You’re right, most European cities I’ve been to have been very walkable in terms of something to explore around every corner, always something to distract. I just wasn’t used to it with Portland but it’s all in the experience! I’m glad you’ve found it too, though and it’s not just me!

  • HannahontheMap says:

    Interesting! People always make Portland seem like this great, quirky place that’s a hippies paradise. I would have pretty high expectations going there too. I’d like to go just to see what it’s about and have my own opinion, it’s always nice hearing someone be honest!

    • Exactly, that was my view of Portland before I went! A big hipster vibe, full of hippie people and quirky bars everywhere – there were some fun places but I thought it would all be easier to find and much more in your face. It surprised me how low key it was compared to the hype… but maybe that’s the point! Whenever you go, let me know what you think, I’d be interested to know!

  • Naomi says:

    My housemate studied there for her year abroad and whilst it sounds great, I think I would struggle there! I’m just not a hipster in the slightest and it at times sounds all a bit much for me. Although, this is taking into account her experience of Reed which is a liberal – liberal being the key word here! – arts college.

  • nixonphoto says:

    Interesting perspective. It’s on my list if places to visit – especially for coffee, donuts and books. Sounds like I can’t go wrong there!

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