Living in Portland, Oregon: A Guide

Vegan strip clubs, naked bike rides and a vacuum museum help keep Portland weird but it’s an easy city to live in. Just don’t tell too many people.

Feature by Reef Younis | 14 Apr 2016

After 12 years of soul-sapping commutes and spiralling rent, I escaped London for the Pacific Northwest. Moving my life 5,000 miles should have necessitated hours of research, obsessive planning and more than a swift 10-day work visit, but Portland’s easy-going charm is extremely seductive.

If you’ve seen Portlandia, you’ll already have a very specific impression of what Portland is about. But despite long-time locals’ vehement objections to the embellished TV perception, the kinks, quirks and weirdness are a huge part of Portland’s appeal. From the cult of Voodoo Doughnut to the World Naked Bike Ride; vegan strip clubs to double-decker fixies; hundreds of dildos inexplicably hanging on power lines to Zoobombing; keeping it weird is in Portland’s DNA, and there are different shades of it all over the city.

It all makes Portland a city of close-knit contrasts that has to be explored. If the above has piqued your interest, these are some of the key factors to consider before packing up for the Pacific Northwest.

Rising rents

Depending on your budget, finding somewhere to live in Portland is tough and is going to get tougher. In 2015, it had the fastest growing rental market with an average rent increase of 12%. With a housing crisis announced in November, occupancy rates almost as high as New York, and property developers on a crusade to build cookie-cutter condos at an exponential rate, be prepared to make a decision on first viewing. When it comes to prices, expect to pay upward of $1,700 per month for a decent-sized studio in the Pearl and popular East-side neighborhoods.

If you’re looking to buy, it’s just as tough. With property prices in big Californian cities reaching unprecedented levels, there’s a wave of investors looking to get more bang for their buck – expect to pay a decent premium on the asking price to nab properties in arty neighborhoods like Hawthorne and Belmont.

East or West?

Split by the Willamette River, a healthy enmity divides those either side of the water. The cleaner-cut West side might be the property developers' postcard impression but with the increasingly sanitized ‘Pearl District’ bleeding into the rough-edged Old Town, you’re still as close to dive bars, homeless shelters, and neon-clad vape stores as you are to boutiques, coffee shops and artisan bakeries.

Home to the Alberta arts district and lively neighborhoods of Hawthorne, Belmont and Mississippi, the East side is still a happy ramshackle mix of record stores, bars, second-hand shops and strip clubs. By day, you can go digging in Beacon Music and Mississippi Records; by night, you often won’t have to leave the street for music venues and bars for early AM drinking.

Fancy a brew?

Portland takes its craft beer seriously. With 58 breweries in the city, and another 84 in the metro area, finding your perfect pint is a drunken artform. Brewpubs are scattered all over but some are worth the extra time and effort. If you’re on the East side, head to Ecliptic Brewing for an IPA in the sunshine or to Stormbreaker Brewing for a fireside Kolsch – both are just off Mississippi Ave. If you’re feeling a little more adventurous, head to Burnside Brewing Co. for a taste of their ‘Sweet Heat’ – a saucy little apricot and Scotch bonnet wheat beer.

When it rains, it pours

For around seven months a year, Portland’s default setting is grey. It averages almost 3ft of rainfall every year (compared to London’s 2ft) and while that all changes for a few glorious summer months, be prepared to invest in a decent waterproof jacket – you won’t regret it.

Summer lovin’

From late May to late September, the sun blazes and the temperature regularly hits upwards of 33 degrees. For active Portland natives, that usually means a sweltering hike, sinking a few beers in the sun or heading to the lakes and rivers 30 minutes or so outside the city. Grab a rubber ring and the factor 50, and drive out to the Sandy River in Lewis and Clark State Park for a riverside BBQ or a few hours of carefree Huck Finn-inspired floating.

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More expats' guides from our Travel section:

 Happy hours and health insurance in New York

 Sydney: schooners and scorching summers

In touch with nature

Portland is surrounded by an abundance of natural beauty. Drive an hour in any direction and you’ll pass mountains, river gorges and national parks. Hiking is a proud pastime, so expect to see cars loaded with iceboxes, trail mix and water bottles on a sunny weekend. With skiing on Mt. Hood, white-water rafting on the Hood River and hundreds of hiking trails, there’s no shortage of outdoor activities for anyone tired of Portland’s relaxed city slicking.

Where to eat

If anything mirror’s Portland’s eclectic personality, it’s the food. From traditional brick and mortar eateries to food truck parking lots scattered around the city, all cuisines are covered. A cursory Google search for Portland’s best restaurants will rarely steer you wrong with the likes of the French-inspired Le Pigeon and the steak-focused Urban Farmer featuring high on the list. While they rarely disappoint, digging into Portland’s strong local food scene is essential. For wings, head to Fire on the Mountain; for Thai, Nong’s and Pok Pok are a must; for BBQ, Smokehouse Tavern is a meat-lover’s delight; for sushi, Bamboo Sushi is always a safe bet and curiously serves up one of the best burgers in town. Honorable mentions also go to Boke Bowl’s Fried chicken steam buns and Aviary’s incredible small plates but if you somehow manage to find a bad meal in Portland, you’re doing it all wrong.

Where to drink

There’s no shortage of dive bars, pubs, and drinking spots to enjoy the fruits of Portland’s brew labour. On the East side, White Owl Social Club, Dig-A- Pony, Rontoms and Sweet Hereafter are lively  locations; on the West, Paymaster Lounge and Low Brow Lounge are decent spots to drink, talk and socialize into the early hours.

Getting recreational

Oregon became the first state to decriminalize marijuana in 1973 and is now one of the few states in the USA where anyone 21 or over can get weed in a state-regulated dispensary. The population of Portland’s never been shy with its consumption, and with over 100 licensed sellers dotted around the city, the choice is yours. If you do go for a smoke, it’s best to keep it private – it’s rare to get cited for it but public consumption is still illegal.

Keeping it naked

Portland claims to have the most strips clubs per capita in the country and there’s plenty of evidence to back it up. Allied with the fact that naked protest and bike riding are perfectly legal (providing you wear a helmet), it lends the city a flesh friendly feel. In Casa Diablo, you can eat vegan food as strippers shed only non-animal- based clothing, and in Acropolis Steakhous you can grab a local T-bone alongside your titillation, but it’s in after-hours places like Sassy’s that help lends an element of blasé comfort to being out and about in your birthday suit. More of a backroom bar than mirror-laden den, in a city where most bars close at 1am, it’s perfectly normal for everyone to grab a seat and a beer, and provide the background conversation to the ladies doing their thing.


Wherever you live in Portland, you can’t escape the plight of the homeless. Despite the best efforts of the shelters, around 4,000 people sleep rough every night. Rampant gentrification on the West (and now East side) and the painful lack of affordable housing haven’t helped, but Portland is a city largely easy with its transient population. Panhandling is relatively rare but expect to be asked for change around downtown and some areas of The Pearl. 

The largest homeless congregations are typically around Chinatown and along Burnside Street where it’s (sadly) pretty common to see a hundred or so people on the pavement outside the mission buildings. Tent cities and small camps are regularly established by bridges and under freeways, and while there aren’t any of the abhorrent anti-homeless measures in place we’ve seen in some UK cities, recent council directives to disband and displace camps have raised tensions.

Hipster stereotypes

Yes, there are plenty of beards, baristas and tattoos but, generally, they all belong to genuinely pleasant people. If your perception of hipster extends to the Shoreditch parody, Portland is a positive exercise in dispelling that myth. Sure, there’s a vegan, organic or gluten-free alternative to almost everything, kale is revered as an essential life force and there’s a touch of self-satisfied piousness in shunning big corporations at every turn, but they’re all symptoms of caring about where you live.

Small talk

Portlanders love it and people will make eye contact and conversation, anywhere. Expect to learn about the merits of pro-biotics in lifts; strangers’ life stories walking the dog; the cashier’s weekend plans as someone else tries to pack your shopping. Admittedly, it’s a friendliness and positivity that takes some getting used to but if you’re worried about moving out by yourself, don’t be: Portland wants to be your friend.