Portland is not the hellscape you’ve been warned about. It’s not quite utopia either. The truth, as always, lives in the in-between—a city running on craft beer, public transit, and a stubborn refusal to be normal.
We checked into the Inn at Northrup, dropped our bags, and hit the streets. Northrup Street itself, named after some 19th-century wagon merchant, sits at the tail end of Portland’s alphabetically ordered grid—a place where urban logic meets pioneer whimsy.
Transit here is more than functional—it’s a civic poem. The MAX glides in from the airport, streetcars clatter toward Pearl District, buses wind into Hawthorn, and a shuttle loops through Washington Park like a friendly ghost. Even the subway station dives deeper than any in America—260 feet underground, as if trying to escape the noise topside.
This is a city of many names: Stumptown, Bridge Town, Rip City, Beervana, City of Roses. Call it what you like, but the drinks flow either way. At the Pharmacy bar. At Matador with happy hour from 10pm to 2am. At Katcha Fabrika, you eat dumplings with vodka in a post-Soviet fever dream. On Mississippi Street, Prost pours Bitburger pils and IPAs to crowds that look like extras from a punk-rock Wes Anderson film. Portland weird: the asymmetric hairstyles, beards, the piercings, the alternative clothing styles.
There’s food, always food. Late-night happy hours that last into the early morning. Brunch lines worth enduring. Food trucks in Hawthorn parked like tribal altars to fusion cuisine. Somewhere between the salmon belly tartare and Voodoo Donuts, we started to forget what day it was - and liked it that way.
Powell’s Books remains a time machine to a pre-Amazon world. One hour in and you’re drunk on possibility. Outside, the Benson bubblers still flow. Matt Groening’s fingerprints linger in the cultural dust.
The Rose Garden bloomed, defiantly, in late October. The Vietnam Memorial was quiet, heavy. The Japanese Garden we left for next time - because there will be a next time.
Portland isn’t a punchline or a political talking point. It’s a living, breathing contradiction. A city with roots in roses and rebellion, thrift and tech, beer and asphalt. You just have to slow down enough to taste it.
