Portland sign at night


A hipster guide to Portland

Published February 1st, 2018

If your measure of a destination lies in the concentration of beards, artisan donuts, craft brews, bikes and other hipster tropes per square kilometre, Portland, Oregon is most definitely your spirit city. Just like in the satirical TV series, Portlandia, art mirrors IRL here where the citizens are woke, fixie culture is life and single origin everything is de rigueur. It’s the city you’ve heard so much about, so here’s why you should go.

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The exterior of the Jupiter Hotel in Portland
The retro motel exterior of the Jupiter Hotel is made for Insta. (Image: Jupiter Hotel)

Where to stay

You’ll undoubtedly spend the majority of your time in Downtown Portland or the Pearl District (where the world’s largest indie bookstore, Powell’s City of Books, is located), but the great thing about Portland is its city block are half the size of regular blocks, so nothing is too much distance to walk or cycle. For a quirky stay, check into Jupiter Hotel – a cool converted motel on E Burnside Street in the Central Eastside (just a 15-minute stroll to Voodoo Doughnuts’ flagship store across the Burnside Bridge, btw). Plus, it’s right next-door to live music venue Doug Fir Lounge for extra hipster cred.


Close-up of a beer flight
It's always hoppy hour on a Brewvana brewery tour (see what we did there?) (Image: Cassandra Laffey)

What to drink

Portland is the craft beer capital of the world (or North America, depending on who you’re asking) with over 65 craft breweries in the metro area (that’s more than any other city in the world) and the first urban cider pub in the US. Beervana Portland Brewery Tours is your hookup to beer heaven with expert tasting tips. I did the three-hour Beer Love in the Pearl walking tour, where self-described beer nerd April took me through the nuances of IPAs, stouts, lagers, dunkels and kölsch (all vegan, btw) via beer flights at Deschutes Public House, Pints Brewing Company and Rogue Distillery and Public House in the Pearl District.


Close-up of a coffee cup
No bad coffee in Portland. Grendel's Coffee House is conveniently close to the Jupiter Hotel, too. (Image: Cassandra Laffey)

If that’s not enough to sate your thirst, there’s also heaps of outlets that sell locally made craft-brewed kombucha on tap, plus the coffee in Portland is pretty decent with 40 artisan coffee roasters within city limits. Head to Cup & Bar at 118 NE Martin Luther King Boulevard on the Central Eastside – a communal space shared by Trailhead Coffee Roasters and Ranger Chocolate Factory with inside spots to dock your bike. Order a mocha to double down on the caffeine rush!


Pink Voodoo Doughnut boxes stacked up
It's all about the pink box...and the Voodoo Doughnuts within! (Image: Cassandra Laffey)

What to eat

Donut worry – if you like your yeasty rings hand-crafted and bursting with irreverent flavour, you’ve come to the right place. Voodoo Doughnuts (with three outlets in Portland) has an international rep for its quirky gourmet raised yeast donuts (and pink decor), but you’ve come all this way so you should definitely sample Blue Star Donuts (there’s seven locations including one at the airport), Delicious Donuts and all-vegan Doe Donuts too. Really, there’s no such thing as a bad donut, according to Beervana tour guide April.


Portland food carts at the Downtown pod
Nong's Khao Man Gai at the Downtown food cart pod is famous for its signature dish of chicken rice. (Image: Travel Portland)

Portland is also famous for its food carts – there’s over 700 vendors in 30 food cart pods across the city including the biggest cluster at SW Tenth Avenue and Alder Street in Downtown Portland with 60 to choose from. Popular food carts include The Dump Truck for Chinese dumplings, Nong’s Khao Man Gai with its signature chicken rice dish, The Grilled Cheese Grill (specialised in toasted cheese sandwiches) and #1 Bento for Korean.  Do a walking tour with Food Carts Portland owner Brett for the lowdown on the food cart scene.


Biketown bike-share cycles docked at a central location in Portland
Portland's Biketown bike-share scheme has eye-catching orange cruisers that references the colour of Nike's shoeboxes – the sporting giant is another Oregon-based company. (Image: Cassandra Laffey)

How to get around

Portlander motorists are notoriously courteous – this is one city where pedestrians really have the right of way and the compact Downtown area is easy to get around. If walking in a straight line is an issue after that brewery walking tour, there’s also the MAX light rail and TriMet system that crisscross the city and a single trip is just US$2.50. Portland is also known as the US bike capital with over 555km of bike lanes and the Biketown bike share program (US$2.50 for a 30-minute ride on one of the orange bikes). Or you could use Uber and Lyft.


Shoes with fall leaves
They're a bit fugly, but trust us, rainboots are a must! (Image: Cassandra Laffey)

Where to shop

You’ve probably clocked that Portlanders rock a particular look known as lumberjack couture. I’m totally making that up, however locals do tend to embrace a practical style that stereotypically includes flannelette shirts, hiking boots and beanies for both sexes. It’s practical (because rain) and also means you can go urban hiking at Washington Park in Northwest Portland in a snap. Waterproof shoes are a good investment, FYI.


The interior of Frances May boutique in Portland
Dress like a local at Frances May in Downtown Portland. (Image: Travel Portland)

Local labels to love include outdoor faves Poler and Columbia, Frances May’s his-and-her streetwear and the tomboy cool of Wildfang boutique. Or be thrifty and get your pre-loved and vintage gear at a slew of second-hand shops in Portland’s southeast.

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Cassandra Laffey

Consumed with unrequited wanderlust, I get my fix in 24/7 cities and hippie retreats. I'm still looking for the ultimate combo of secluded beach and major metropolis, and my happy place is a 5-star hotel room all to myself - sigh.