After voting to professionalise the Oregon city’s government in 2022, Portlanders are reinvesting in the city with new shops, restaurants and cultural venues.
When Monocle unveiled its annual Quality of Life Survey earlier this month, US cities continued a run of gutter balls that now stretches nearly a decade. The most recent – and only – stateside entry to ever feature on our list was Portland, which last nabbed a spot in 2017.
The years since have not always been kind to Oregon’s largest city. In 2020 and 2021 destructive street protests, violent acts of political extremism, escalating homelessness, rising crime and a disastrous statewide drug-decriminalisation scheme all contributed to drastic reductions in quality of life that caused the once fast-growing city to shrink for the first time in decades.
In 2022, however, Portlanders voted for one of the farthest-reaching municipal reforms in recent US history – the professionalisation of the city’s government. And since 2024, city and state leaders have taken corrective action, including standing up much needed shelter beds, ending laissez-faire policies on public drug use and ensuring that protests remain peaceful and do not veer into property damage.
In the wake of these changes, a new wave of shops, restaurants and cultural venues have been opening – many of them in the city centre, which just a few years ago had been written off as a moribund office district that would never bounce back. The influx of new businesses could help the city take off once again.
Here are five addresses you should know for your next visit to Portland.
While there is surely somewhere in Portland to practice the Queen’s Gambit, this Chess Club is a paean to print, or as the owners put it: “A playground assembly of visual cultures.” There are more than 400 magazines and design books for sale, including lush glossies such as contemporary art mag Hi-Fructose and food and fashion mash-up Family Style. Chess Club also aspires to cultivate local print culture – it’s a must-stop location during the Portland Art Book Fair and hosts a recurring workshop, How to Start a Magazine, that might just yield the next great title in the city that birthed Kinfolk and Berm. In September 2026, they will move 15 blocks from Old City to the heart of downtown with the promise of more space for the printed word.
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