Morning

You’re bound to hit up Old Town at some point today where the “Keep Portland Weird” mural is, so let’s just get this out of the way. Take your darn photo.

After hashtagging your latest tourist trap, fuel up. Voodoo Doughnut is right across the street. If you don’t mind standing in a long ass line for your Bacon Maple Ale and Chocolate doughnut with the rest of the tools, then by all means. For an insider tip, Blue Star Donuts has several locations throughout Portland, and is just as good (or dare I say, better) without the ridiculous wait. Ponder the correct spelling for doughnut while in line. Or just skip it altogether and head to Mother’s Bistro and Bar for a real breakfast. Then putz around Old Town for a bit, taking in Portland’s once shoddy stomping ground for brothel-going, drunken sailors. The strip club culture still runs deep, if that’s your scene. Mary’s Club, located on the corner Southwest Broadway and the somewhat shady alley on Ankeny Street is the longest running strip club in Portland. For a legit history lesson on Portland’s corrupt underbelly involving brothels, gambling halls, saloons, and kidnappings, consider taking a guided Underground Tour through Old Town-Chinatown’s Shanghai Tunnels, where you spend an hour and a half winding through creepy dank passages that are supposedly haunted by boozy ghosts.

If history isn’t your bag, or just admit it, you’re scared of the dark, head over to Washington Park, via the Max Light Rail, which costs $5 for a day pass, and is worth it if you plan to get around by public transportation. Or take Uber or Lyft, which would be fastest. Or you can rent a bike and haul it there by two wheels, saving the light rail for those extremely hilly sections. Because you are pretty much going uphill all the way there. Meander through The International Rose Test Garden (Portland is nicknamed “The City of Roses” after all), or have a “zen” experience relaxing by the would-be tranquil waterfall in The Japanese Garden. I say “would-be” because it’s probably infested by other wannabes doing the same damn thing.

Noonish

Head downtown and stop by the Alder Street Food Cart Pod for some quick grub. You may find yourself circling around several times what with all the options. Take your lunch and head over a few blocks to Director Park, then find a seat and feed your trap while watching people make fools of themselves playing the giant chess game. After lunch, walk (6 minutes) to Ace Hotel and order a coffee from Stumptown Coffee Roasters. Then take your beverage and make your way to the upstairs lobby and plant yourself on one of the plush couches. Hang out for a bit and maybe catch up on some reading, then go to the lobby photobooth, pay $5, and flash your dumb smiling face.

Afternoon

Once you’re properly fed, caffeinated, and rested, walk (2 minutes) to Powell’s City of Books. You want to spend a few solid hours weaving your way around all 3,500 sections because it’s possibly the best place ever. Grab a book that seems interesting, go to the store cafe, and check out the smart-looking attractive people while pretending to read. Powell’s has a nice travel book section, just in case you wanted to get some more info on the city. Another tip, if you’ve been lugging around books that you don’t want anymore, go to the Orange room and sell your book. As long as the pages are not falling out, or it was brutally massacred by your dog somewhere along the line, they most likely will buy it. But don’t count on making too much. Maybe it will get you a beer…

That said, wander over to Deschutes Brewery (3 minutes walk) for a Fresh Squeezed IPA and people watching. After achieving that warm buzzy feeling, walk your happy ass over to Pearl Bakery (another 3 minute walk) and get a croissant to-go. Then head to Governor Tom McCall Waterfront Park (walk 20 minutes or bike 8 minutes) find a nice grassy spot, or sit by the fountain and chill while taking in some scenery by the Willamette River. Eat your croissant. Take a nap, or whatever, but don’t get robbed. Or go for a leisurely stroll along the waterfront.

After 4pm, head to Departure Restaurant + Lounge for happy hour (9 minute walk from the park) located on the 15th floor of The Nines hotel. Enjoy some great city views of Pioneer Courthouse Square and the waterfront while liquoring it up. Don’t worry about looking fancy here, Portland doesn’t give a shit. This is a city where you’ll find well-suited business men and flannel-wearing hiker dudes sitting next to each other at a bar. Sure, maybe one is downing a PBR while the other is nursing a Perfect Martini, and they probably are not friends, but it’s all good.

Evening

So, enough downtown. Time to head over to the other side of the river, where you’re much more likely to find hipsters in their vintage tee, scarf-wearing — even if it’s 98°out — glory.

From Pioneer Square you can walk (1 hour) bike (20 minutes) or walk to Southwest Salmon Street and 5th Avenue and take the Max light rail (20 minutes) across the river to Southeast Division and 30th. If you like seafood go to B + T Oyster Bar, or if you feel like dropping some serious dough, make a reservation at Roe, the “secret” seafood restaurant hidden inside the oyster bar — Note that unless you reserve weeks in advance, it’s pretty much impossible to get a seat. Or, hit up Bollywood Theater for some Indian street food — I particularly like their Aloo Tikki.

After dinner, take a stroll around and let the food settle. Think about what you might want to do tonight since you still have about 10 hours in Portland. This will also give you some time to engage in deep questions, like why on earth Portland has a vacuum cleaner museum.

As for tonight, perhaps you will end up at a concert at Doug Fir Lounge and knock elbows with the cool kids. And maybe after that, see some dancers at Union Jacks.

Or maybe you will have yourself a mellow evening and catch a flick at Baghdad Theater. But then afterwards realize you’re still young(ish) and find yourself at Space Room Lounge & Genie’s Too for cheap whiskey and debauchery.

Or maybe you will join the Puddle Cutters moped gang and just stay here forever.

Did I mention Portland is weird?

10 Tips for 24 hours in Portland

  • Rent a bike
  • Buy a day pass from TriMet at one of the kiosks. It’s good for the Max and bus
  • Drink local coffee and beer
  • Visit a public park
  • Check Portland Mercury for the latest concert listings
  • Come in the summer or bring a raincoat
  • Eat at a food cart
  • Visit at least one vintage store (you know you want to)
  • Buy a vintage knick knack for your parents, they’ll probably love it
  • Walk across the Hawthorne Bridge