“How can you be a libertarian and live in Portland?” I’ve heard variations on this question a lot in the fifteen years since I left my job at a libertarian think tank in DC to move to one of the most progressive cities in the US. It’s especially relevant now, as perception of the city post-2020 has shifted from quirkily liberal to violently chaotic. The question was posed again recently by a visiting friend, which prompted me to write up this answer.

What is there for a libertarian to like about the politics of Portland, Oregon? Quite a lot, actually.

Ending the drug war has long been one of the top priorities for libertarians. Oregon is a pioneer at liberalizing drug laws, becoming one of the most liberal drug jurisdictions in the world. We were the third state to legalize recreational cannabis. We are the first to decriminalize possession of all drugs. We are the first to implement legalized psychedelic therapy. You can debate how well some of these policies are working out or argue that our moves toward ending prohibition haven’t gone far enough, but where in the US is trying more libertarian drug policy than we are?

Politics aside, one of the things that first attracted me to Portland is its dynamic dining scene, driven in part by food carts that offer niche cuisines and serve as an incubator for entrepreneurs before they go brick and mortar. A report from the US Chamber of Commerce concludes that Portland’s light touch regulations make it the number one city in the country to operate a food truck. “Obtaining all the permits and fees to start a mobile food business in Portland costs just $1,877 compared to $6,211 in Seattle,” reports Eater. And “there are few restrictions on when, where, and how they can operate. In Portland, food carts can remain permanently on almost any commercially zoned parking lot.”

What about alcohol? Oregon is a control state with high taxes for liquor, though in my experience it’s the most consumer-friendly of control states when it comes to selection. Our liquor restrictions are at least partially offset by the ease of getting an on-premise license, which costs just $800; compare to six-figure prices in quota states like California. Our beer taxes are low. Cocktails to-go are permanently legal. Despite our control state status, the huge numbers of breweries, wineries, distilleries, and excellent bars contradict any suggestion that Portland is an oppressive place to be a producer or consumer of alcohol.

Like many cities, Portland has inflated housing costs due to restrictive zoning. Unlike many cities, Portland is doing something about it. The Residential Infill Project passed in 2020 is “the most pro-housing reform to low-density zones in US history,” according to the Sightline Institute. It legalizes up to four homes on residential lots, up to six with regulated pricing, and removes parking mandates from most of the city. Additional reforms passed in 2022 won praise from Reason’s Christian Britschgi. The changes aren’t perfect, but overall they’re a big win for property rights.

How about bodily autonomy? On reproductive rights, Oregon is among the most liberal in the country for access to abortion. At the end of life, Oregon is one of eleven states allowing patients to seek medical aid for assisted suicide.

The state does have capital punishment, but recent reforms drastically reduced its scope and previous governor Kate Brown cleared death row by commuting all existing sentences to life without parole, effectively taking the state of Oregon out of the business of executing residents.

Without endorsing all aspects of the 2020 protests, the core motivation was a sound one. As I wrote at the time, “I’m sure I disagree with marchers on any number of issues. But on the one that matters — the dignity of all people and their right to live free from the fear of state-sanctioned violence — there should be no disagreement about the justice of their demands.”

Portland was far ahead of the curve on same-sex marriage, with Multnomah County issuing more than 3,000 same-sex marriage licenses beginning in 2004 (regrettably later overturned by a statewide referendum and court case). Portland remains a very LGTBQ-friendly city.

Oregon has been a sanctuary state for immigration since 1987, the first in the country to pass such a law. The law was further strengthened in 2021. Portland is also a sanctuary city (mostly redundant given state law, but worth noting.)

There’s a reason Portland has so many strip clubs and the world’s most well-attended naked bike ride: protections for free expression, including via nudity, are stronger in the Oregon constitution than under the First Amendment. (Though do read about the dark origins of the court case setting that precedent.)

As of this summer, drivers in Portland even won the freedom to pump their own gas.

Of course, none of this is to suggest that Portland is a libertarian utopia, but where is? Do libertarians who move to red states get asked how they can stand to live there? If I moved back to my home state of Texas, I don’t imagine nearly as many libertarians asking such a question. Yet Texas threatens long prison sentences for things like selling weed or performing an abortion, which strikes me as barbaric compared to how we do things in Oregon.

My impression is that the frequency with which I’m asked how I can live here reflects an outdated perception that libertarians should feel more at home on the right than among the left. There were some eras when this was truer than others, but it’s certainly not true right now, and the liberty movement has always been more diverse than the legacy of Cold War era fusionism suggests. (See Matt Zwolinksi and John Tomasi’s excellent new book on the topic or my review of it here.)

As the late Steve Horwitz observed in when Trump took office in 2017, “Too many libertarians are too focused on economics” and “[… too] many libertarians hate the left more than they love liberty.” Economics is important, but on substantive issues where the cruelty of the state is most forcefully imposed, humane and liberty-enhancing policies often come more from the left than the right. Democrats are currently much better on the preservation of liberal political institutions too, now seriously threatened by the Trumpist GOP. (For all the justified criticism of some Portland protest tactics, it wasn’t the left that tried to overturn a presidential election, violently overran the Capitol, chanted about hanging Mike Pence, and nearly incited a constitutional crisis.) Portland has some dumb economics — can we kill the arts tax, please? — but there’s much else here that libertarians should applaud.

Obviously there is plenty I disagree with in Portland and Oregon politics, some of which I’ve written about. There’s a bland uniformity of thought here which one may be wary of running afoul of if involved in a public-facing business. I’d like lower taxes and less regulation. I’d like more respect for property rights; protesters shouldn’t smash windows of random buildings and businesses should be better protected from property crime. I cringe when I hear some locals talk about the evils of capitalism and I wouldn’t want the median Portland voter setting national economic policy. Cato’s “Freedom in the 50 States” report summarizes, “Oregon is among the worst states on economic freedom but despite a relative slide remains a top-10 state on [personal] freedom.” I don’t expect Portlanders to become ideologically libertarian, but the city would benefit from becoming a little more neoliberal.

The post-Covid hollowing out of downtown and general failures of governance are a genuine blight on the city; the official Portland motto boasting its status as “the city that works” now comes across as a joke. (“Let it ride,” the Bachman-Turner Overdrive-inspired motto suggested by 1980s mayor Frank Ivancie, would be far more apt.) Yet there are reasons for cautious optimism. Voters decided last year to completely overhaul the city government, implementing charter reform and ranked choice voting that will take effect in our next election. The city is trying out expanded enterprise zones with tax abatements. It feels like ages since we had a freakout over something trivial like white women allegedly appropriating burrito recipes; right now anyone opening a business feels like a victory. The recognition that we need pragmatic revival is palpable.

The quality of life is what attracted me to Portland, and despite the city facing some very real problems, I still find it an appealing place to live. I came here to bike to coffee shops, not hang out with libertarians. But to the extent that ideological alignment matters, I could do a lot worse than here.

A libertarian can live in Portland the same way they can live anywhere else: by engaging thoughtfully with their neighbors, advocating for positive changes, and putting politics in its place by making room to relate to others in non-political roles. A better question than asking how a libertarian can stand to live here is asking why more of them don’t. If one gets over bias against the left, you can make a pretty solid case that in policy if not ideology, Portland is among the more libertarian cities in the US. And the coffee’s pretty great too.