1. You stroll through a farmers market outside of the city center.
The downtown farmers market at Portland State University is definitely a must-stop at some point, since you can pretty much spend an entire morning grazing the goods of local food vendors. If you want a more neighborhood vibe and don’t feel like waiting in a long ass line for a tamale, head to one of the smaller markets, like the Irvington Farmers Market or the Montavilla Farmers Market.
2. You have a turkey meal and Spanish coffee at Huber’s Cafe.
It’s a Portland classic, and the oldest restaurant here to date, established in 1879. Back in its heyday, customers would get a turkey sandwich and some coleslaw for free if they ordered a drink. Unfortunately this is not the case anymore, nor is Huber’s quite the hot spot it once was. But it’s a Portland staple, and worth the trip just to see the pyro show that goes into preparing that Spanish coffee.
3. You frequent one of the many dives that are not overrun by tourists and hipsters (at least not yet anyway).
Depending on the caliber of cleanliness, beer options, and overall unassuming vibe you’re seeking, there are many dives that have yet to be discovered by tattooed badass-wannabe millennials. One such haunt is My Father’s Place, a quirky enclave in the otherwise trendy Central Eastside Industrial District. A classic joint with all day breakfast and a weird mix of barflys, you pretty much see anyone from families breakfasting to drunken degenerates downing whiskey at 11am — which keeps it interesting, to say the least. It was also a regular hangout for Portland musician Elliott Smith, whose smoke rings probably still stain the carpets.
4. You take a walk through Peninsula Park Rose Garden.
So you’ve probably visited the International Rose Test Garden because it was one of the first things people told you to do in Portland. Yet many folks have never been to the original rose garden in North Portland. A much smaller scale, but it’s a chill park where locals walk their dogs or hangout on a lazy afternoon. Avoid going at night though, as it’s a bit sketchy after dark.
5. You peruse one of Portland’s smaller independent bookstores.
6. You eat at a doughnut place other than VooDoo, Blue Star or Pip’s Original.
Believe it or not, there exist doughnuts eateries in Portland besides the artisan stomping grounds we all know and love. Maybe you won’t find some crazy fried dough concoction that involves bacon, but spots like Annie’s Donuts and Helen Bernhard Bakery serve quality no fuss doughnuts that are just as good or better — and with no lines.
7. You watch a sunset at Skidmore Bluffs.
Perhaps it’s more crowded than it was a few years ago (like everything else in Portland) but this north Portland hangout is a cool spot to grab a picnic and relax, away from the craziness of downtown.
8. You do happy hour at a local joint that is a bit out of the way for those other than residents.
Rather than stay close to the city center, head out to some neighborhood bar which doesn’t involve (cough) the yuppie pretension that’s becoming all too common here. Slingshot Lounge is a good one.
9. You walk through Old Town and imagine what it probably looked like twenty something years ago when Gus Vant Sant filmed My Own Private Idaho and Drugstore Cowboy.
Newbies or travelers who want a visual of what the old downtown used to look and feel like should just watch these films. Portland’s seedy past is still evident within the bowels of Old Town. While it’s definitely overrun with tourists going to VooDoo Doughnut, taking a ramble through this area offers a glimpse into its gritty landscape of strip clubs, porn shops, and neon — which are still here — but now seem more of a gimmick than a grime-ridden underbelly.
10. You explore the ethnic food scene along SE 82nd Avenue.
Take a look around and you will be able to find some family-run restaurants cooking up authentic dim sum or pho. Plus, at least you can find some pockets of culture here that are hard to find in trendy hoods once Portland started to become “the place for young people to go and retire.”
11. You hang out in neighborhoods east of 82nd Avenue.
Before that’s taken over by vintage boutique stores and craft breweries like the rest of Portland.