The Portland mini break

One of my 2016 goals is to travel more around the US. This country is vast, varied and beautiful, with enough must-see places to fill a lifetime. That’s probably a reason why many Americans don’t leave to go on vacation (as well as the abysmally low number of personal leave days).

To that end, I’ve lined up a number of fun long-weekend destinations to hit up over the course of the year. First on the list was the artfully hip, the achingly cool and the wonderfully weird city of Portland, Oregon.


We looked all over for this guy, he looks like fun

My travel companions were a group of my Irish besties who are over in SF for a work conference. We’ve known each other for 10 years and love nothing more than to take ourselves off for sneaky city mini breaks. And given the fact that we do eating, drinking and general aimless wandering pretty well, Portland was the perfect destination for us.
The city and the sights

Whilst there are tourist attractions in Portland, it’s not like the bigger cities, where you’re rushing around trying to check all the sights off a list, frantically trying to grab at least one good shot of the experience for Instagram. (If it’s not on Instagram, it didn’t happen).

A weekend in Portland is more about soaking up ‘the vibe’, and trying to experience it as a local (hipster) would.

(I realise the irony of this. No self-respecting Portland hipster would ever do anything as contrived as trying to fit in with the locals. They’d rather eat their own vintage vegan clogs.)

This city is so livable – just like SF in my mind. It’s a collection of super walkable districts on either side of the Willamette river. Each district has an infinite number of kooky stores (which mostly sell perfumed products and hipster cat paraphernalia), fairy light bedecked restaurants, warehouse style breweries and funky food trucks.


Sacred heart candles get a makeover in a Portland store. Is praying finally cool? Unclear…

There’s a fairly industrial vibe to some parts of the city, which surprised me a little. Or maybe urban hip is a better way of describing it. It kind of reminded me of the Dogpatch in SF.

There are definitely classically beautiful parts of the city – the riverfront is lovely, with a view of Mount Hood. And there is an abundance of cherry blossoms flowering at the moment, which I was thrilled about – I’m a big fan of their work. Huge.

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Ahhh, cherry blossoms with cherry blossoms


Fun things to do include a spin around the Portland Saturday Market (also open on Sunday, never fear) and a browse around Powell’s City of Books (an entire city block dedicated to books). We also wanted to try the aerial tram, but it was closed sadly.

All fun things, but really, Portland is all about the eating, drinking and people watching…

The eating and the drinking

When I asked around for generic Portland recommendations, I exclusively got back restaurant and bar suggestions. I thought San Francisco was a foodie city, but Portland takes the biscuit (food related pun intended).

Artisan donuts, craft beer and pinot noir seem to be the main things to try when you’re there. And we tried them all!

Donuts: The best known donut store is Voodoo donuts. The line was out of control though, so we grabbed a quick pic for posterity (ie Instagram) and then buzzed over to Blue Star donuts.


Come for the donuts, stay for the tech lols. I especially like the last one

Craft beer: There are sooooo many breweries around, 1 brewery to every 1.5 hipster apparently. Somebody recommended Deschutes to me, and not knowing much about beer, we went with it. A bustling, wood-beamed, vaulted ceilinged warehouse, with a massive selection of beer and tasty fries.

Pinot Noir: I don’t have much to say on this matter. I’m not a fan. Napa Cabs till I die…

Other restaurants: 

  • Pok Pok is a really cute Thai place, that all the locals RAVE about. Think picnic tables and stainless steel plates. The food was out of control. We didn’t go for the chicken wings (which are famous apparently. I’ll regret that until the day I die.
  • Tasty n Alder has amazing brunch food and cocktails, including the best Bloody Mary I’ve ever had made from Tequila! I’ll forgive them for the 1.5 hour wait.

Unfortunately for me I missed out on a lot of the culinary adventures. I had decided that this was the week I would give up gluten and sugar…again. If I could survive a weekend in Portland, off the hard stuff, I could survive anything. Actually, turns out it’s probably easier to do in Portland than anywhere else. Every time I inquired about gluten/sugar free options the server would present an entire allergen-free menu with a flourish – not an eye roll or judgey sigh to be seen or heard. Portland is my spirit animal.

It still wasn’t easy though. The others got a bit sick of my constant staring as they tucked into their sugary, glutenous treats and my persistent requests to have a sniff, or asking them to describe their eating experience in salacious detail. Salacious…

The people watching

The first thing that comes to mind when you think about Portland is the people. Specifically the hipsters.

Portlandia has a lot to do with this obviously, but there’s no smoke without a hand-rolled cigarette as they say – and the people of Portland are without a doubt, off-the-charts cool.

(I wish I could think of a better word than cool – it’s so not cool).


And it’s not just the tattoo sleeves, lumberjack beards or beany hats that make them this way. It’s a quiet, unflashy confidence that simply oozes out of their pores. Oozes in a sexy way? You know they couldn’t give a shit about what you thought of them. And equally, you get the impression they’re not thinking about or judging you at all. (For better or for worse).

One of the slogans of the city is ‘Keep Portland Weird’ and there are definitely people who embody this to the full – from the no-pants wearing shop assistant (he was just getting prepped for the naked Sunday Shopping spree at 4pm) to the girl who ran up to the restaurant window where we were sitting, blew on the glass, drew a heart and then ran off.

All of them are amazing.


Real naked life, right here!


The company

All of us girls have pretty similar travel styles – we like to have a loose enough itinerary so we’re not missing anything vital, with solid dinner reservations so we’re not wandering around in a hangry panic looking for something to eat. Generally, we’re just content to take the weekends as they come, which makes for a very relaxing, no stress vacation.

Aside from marveling at the city and talking (obsessively) about the food
we spent a lot of time playing Cards Against Humanity, answering the 36 Love Questions, talking about weddings (we have two upcoming nuptials and one new engagement), singing Justin Bieber songs and complaining about Justin Bieber songs getting stuck in our heads.

All in all Portland provided the perfect backdrop for two wonderful days of catching up and reminiscing, side clutching laughter and emotional D&Ms,  Irish craic and good, clean American hipster fun.


1 thought on “The Portland mini break

  1. Pingback: Reflections on Rain on a Rainy Day in SF | 100 Days in SF

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