By Skye VernonPortland does not have a lack-of-things-to-do problem.
It has a prioritization problem.
People come here for food. They come here for weird little shops, queer culture, strip clubs, weed, art, bars, forests, hiking, camping, and the feeling that the city might still have a personality that has not been sanded down into a luxury-apartment lobby. The people who already live here like a lot of those same things.
And somehow the city acts like none of it connects.
There are empty buildings everywhere. That is not just something people say because downtown feels sad. The City cited a 34.7% vacancy rate in the Central Business District at the end of 2024. Its answer is a $1.19 million vacant-space project, including $550,000 for leases, rent subsidies, and programming. I am glad that project exists. But look at the size of the hole and then look at the size of the bandaid. The City’s own project page says the quiet part out loud: it is trying to help entrepreneurs, nonprofits, and small businesses get into unused commercial space because there is that much of it.
There are small business districts that feel hard to reach unless you already know exactly where you are going and have a car or enough money to keep ordering rideshares. There are people who would gladly spend a wet winter night going out for dinner, a show, a club, a drag night, a weird event, or just somewhere to exist around other humans, except getting around becomes such a pain in the ass that they stay home instead.
Then everyone shrugs and says Portland is dead in the winter.
It does not have to be.
The City Already Has an Identity
Portland has spent a long time being suspicious of big corporate expansion. Residents tend to care about local businesses, independent restaurants, strange little stores, artists, and places that feel like they could not be dropped into any other city unchanged. That is not a weakness. That is the product.
The city should stop treating that identity like an accidental side effect and start building an economic strategy around it.
Not by turning every neighborhood into a tourist trap. Not by replacing what people like with a row of chain stores, branded murals, and $19 cocktails named after the color beige. I mean making it easier for people to find, reach, and spend money at the places that already make Portland worth visiting.
Hawthorne is a good example. It is a 43-block run of restaurants, carts, bars, vintage stores, theaters, bookstores, and small businesses. Hawthorne Asylum alone has more than 20 food carts. That is a whole destination, not a side street. Travel Portland’s own guide is basically a list of reasons someone could spend an entire day there.
But Portland mostly leaves people to discover the route, figure out where the useful stops are, and work out how they are getting home after the normal transit day has already started winding down.
The same is true for nature. Portland is surrounded by trails, forests, rivers, camping, and outdoor places that people would kill to have near them. Yet visitors often have no idea how to get to those places without renting a car, already owning camping gear, or knowing somebody local. It is bizarre to be a city with this much nearby nature and make it feel like a secret you are supposed to discover through trial and error.
Transit Is Part of the Economy
People talk about public transportation like it is separate from business, nightlife, tourism, or public safety. It is not.
If people cannot get to a restaurant, venue, shop, trailhead, or event at the hours it is open, that place loses customers. If they cannot get home safely afterward, they leave early or do not go at all. If the winter weather makes an already inconvenient trip worse, the city loses an entire season of activity.
Portland has late-night replacement buses for MAX lines. That is better than nothing. But compare that with Vancouver, a city that also sells itself on food, nature, neighborhoods, and nightlife: its NightBus network has 10 routes, runs every 20 to 30 minutes, seven nights a week, and has a central, well-lit downtown departure point. I am not saying Portland can copy and paste Vancouver. I am saying somebody over there understood that a city where people go out needs a fucking way home. TransLink’s NightBus information
Meanwhile, Portland Streetcar’s published Saturday service ends around 11:30 p.m., and TriMet’s late-night MAX buses are replacement service, not a citywide overnight network. TriMet’s late-night MAX service and Portland Streetcar’s service standards spell that out. That is before many concerts, movies, dinner reservations, club nights, and bar shifts are even over.
Then there is I-84. The Banfield stretch between I-205 and I-5 gives westbound traffic only two exits, while eastbound traffic has five. So when westbound 84 locks up because of a crash, weather, or one bad merge, people are not just delayed. They are stuck in a funnel, watching the rest of the road system clog around them because there are barely any ways to get off. Go look at the ODOT traffic map next time it happens. It is not subtle.
That does not only ruin a commute. It makes a night out, a trip downtown, or a connection from the east side feel like a gamble. A city that wants people to move around needs routes that fail gracefully when something goes wrong.
Use the Empty Buildings
The abandoned buildings are where this becomes impossible to ignore.
Why are there so many spaces sitting empty while Portland keeps talking about the disappearance of third spaces, affordable gathering places, arts venues, and places for people to just be? Some should be housing. Some should be community space. Some could become night markets, small performance venues, cooperatives, low-cost studios, indoor winter event spaces, queer community hubs, or flexible places where local people can put on something weird without needing a giant corporate sponsor.
The city does not need to own every building forever. But it could have a serious acquisition, renovation, land-bank, or partnership strategy instead of allowing vacant properties to become part of the scenery. If a building is privately owned, the owner and its permit history can be checked address by address through PortlandMaps. What Portland does not have is one clean public ledger that tells you who owns every vacant commercial building, how long it has been empty, and why it is sitting there. It should.
Even modest, useful spaces would matter. A heated indoor spot where people can gather in winter matters. A small venue with a functioning bathroom, decent transit access, and a layout that does not trap everyone in one line matters. A place for pop-ups, DJs, vendors, community groups, and small businesses to test an idea without gambling their entire life savings matters.
The city keeps acting surprised when people say there is nowhere to go. Some of the answer is literally sitting there boarded up.
Stop Acting Like Money Is Dirty
Portland does not need to become a city that worships developers or treats every local business like it needs to become a national chain. But there is a difference between protecting a city from corporate takeover and refusing to help it generate enough activity to support the people already trying to build a life here.
Tourism is not automatically soulless. People spending money at independent restaurants, local hotels, clubs, dispensaries, shops, artists, guides, markets, and events can keep more of the city alive. A better internal economy means residents have more choices too. It means businesses have a better chance of surviving winter. It means more reasons for people to go outside and meet each other. It means a city that is not permanently waiting for someone else to save it.
The question is whether that money stays connected to local people and local places, or whether Portland gives up and lets somebody else package its identity for it.
This Is a Thought Experiment, Not a Magic Wand
I am not saying a mayor can wave a hand and fix every empty building, bus route, parking issue, freeway ramp, or struggling business. Portland has real budget limits, agency limits, state rules, neighborhood conflicts, and people who will object to literally any change that happens within twelve blocks of their house.
But that is exactly why the city needs a clear direction.
I would start from a simple question: what already brings people here, what keeps residents from enjoying it, and what would make that ecosystem stronger without selling it off?
Then I would treat housing, transit, safety, tourism, nightlife, small business, nature, and public space as connected problems instead of throwing each one into a different department and hoping for the best.
Portland has an identity. It has culture. It has nature. It has people who want things to do and places to belong. It has buildings that could be useful. It has small businesses trying to survive. It has enough raw material to be one of the most exciting cities on the West Coast.
What it does not seem to have is a city government willing to put those pieces together on purpose.