True Grit: A Beginner’s Guide to Portland

By: Crai S Bower

January 27, 2014

Big Pink and downtown Portland, Oregon with Mount Hood in the distance.

The first general observation one makes about Portland is a pervasively cool grittiness. Seattle and (especially) Vancouver have doggedly scrubbed their “skid row” self-images, but Portland still takes great pride in its rougher edges, preferring to maintain its historical image as the ragged-cuffed logger.


A Beginner's Guide to Portland | Stumptown Coffee

Stumptown Coffee © Crai S Bower

Funny thing is, America’s become obsessed with this aesthetic – bushy bearded, growler toting bards riding fixed gear bicycles to their local Stumptown Coffee. People often associate this image with the entire Pacific Northwest or, more recently, with Brooklyn (“Portland of the East Coast”), but the truth is this curated “grittiness” emanates from just one place, and that place is Portland.


It’s fitting that two men who set off paddling a canoe founded Portland, given the city’s eventual envelopment of the Willamette River and embrace of the outdoor lifestyle. The pair’s disparate occupations, Asa Lovejoy was a lawyer, William Overton was a drifter, perfectly reflect the city’s oxymoronic personality of “erudite slacker.


A Beginner's Guide to Portland

Bike to beer ©

By 1850, a thriving port had sprung up not too far from that original landing, but naming the city had nothing to do with the shipping industry. The town’s name was settled in a coin toss won by early settler Francis Pettygrove, who wished to honour Portland, Maine, his hometown. Had he lost to Lovejoy, we’d be talking today about Boston, Oregon.


Portland possessed about 1,000 people when it incorporated in 1851. The Portland Street Railway Company began in 1871 and, unlike most other American cities, it has never looked back. Today’s TriMet MAX is the finest surface light rail system in North America, contributing greatly to Portland’s cosmopolitan feel. MAX lines are even responsible for the gentrification of several industrial neighbourhoods. This trend will continue when the Orange Line opens along Division Street in 2015. Today’s visitors can still travel virtually anywhere in greater Portland on MAX.


MAX | A Beginner's Guide to Portland

Tri-Met Max ©


Portland touts many “Only in Portland” eccentricities, so much so that comedians Fred Armisen and Carrie Brownstein exploited Portland’s quirkiness as the foundation for their hit television show, “Portlandia,” now filming its third season around town.


Wandering the city anytime can feel like a visit to the “Portlandia” set. Cavernous Powell’s Books really does occupy an entire city block. Voodoo Doughnuts actually do carry bacon-covered maple bars. You can, in fact, count over 600 food carts scattered across the city. And, yes, it does seem sometimes that every Portlander sports a full beard, flannel shirt and “workhouse” boots. Even the women!


Food cart | A Beginner's Guide to Portland

Foodcart scene © Crai S. Bower


Overton and Lovejoy settled Portland for its potential natural resources, but they also noted the undeniable beauty of “this forest ringed with mountains.” Visit Forest Park and you can almost experience what they saw. This 5,100-acre hillside wilderness perches in the West Hills northwest of the city centre. The system of rough paths cut through segments of old growth places Forest Park among the finest urban forests in the world. Portland Japanese Garden, located in adjacent Washington Park, celebrated its 50th anniversary in 2013. The garden showcases eastern horticultural traditions and provides the finest views of the surrounding environs, including Mt. Hood, a Mount Fuji doppelgänger.


Japanese Garden | A Beginner's Guide to Portland

Portland Japanese Garden © Crai S. Bower


Whether strolling through Portland Art Museum‘s sculpture park, stopping off at See See Motor Coffee Co. or exploring the Portland Riverwalk, it’s impossible to miss this city’s gritty urban aesthetic.


Header photo: Skyline with Mt. Hood ©


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Have you been to Portland? Where are your favourite places to visit in town? Let us know in the comments below.


Written by Crai Bower


Crai S Bower

Award winning travel writer, photographer and broadcaster Crai S Bower contributes scores of articles annually to more than 25 publications and online outlets including National Geographic Traveler, Journey, American Way magazines and T+L Digital.

Categories: Our Places