1. Find a new book at Powell’s.
It’s the City of Books, and you’ll need a map to traverse it.
2. Get your birthday fix at Pip’s Original Doughnuts.
Skip the line at You-Know-Where and head to Pip’s for tiny made-to-order doughnuts and homemade chai tea. Visit on your birthday week for a dozen free.
3. Play B-Movie Bingo or watch TV reruns at Hollywood Theater.
This historic 1920s nonprofit theater sells pizza, beer, and popcorn and has regular film events. Catch B-Movie Bingo on the first Tuesday of every month, or the Cinema Classics on Saturdayy and Sunday afternoons. For a quirkier night head to ReRun Theater, which screens old TV shows (and their commercials) like He-Man, The Six Million Dollar Man, or The Bionic Woman.
4. Picnic on a dormant volcano
Bring your treats and a blanket to the top of Mt. Tabor, a dormant cinder cone volcano right in the middle of the city.
5. Sip the water of life at Multnomah Whiskey Library
The offerings at the Multnomah Whiskey Library include over 1,500 bottles all on display. Knowledgeable and distinguished waitstaff offer cart service to sit-down patrons.
6. Find a zine at Reading Frenzy.
Check out some hard-to-find zines or give them your own to sell at this Independent Press Emporium.
7. Cheer on the Dragonboats.
Cheer on your team or just the coolest-looking boat at the annual Dragonboat races on the banks of the Willamette River. This summer event has been running for over a quarter of a century.
8. Participate in the Naked Bike Ride.
Since it’s legal to be naked when it’s a protest, this city-sanctioned bike ride lets riders bare all every June.
9. Escape the rain with a cocktail.
Watch the city’s master mixers in action, combining small-batch ingredients and local spirits into something eminently sippable. You have your pick from hundreds of bars, including Kask and the underground Pepe Le Moko.
10. Tour the world’s cuisine at the food carts.
They’re affordable and delicious. Waffle sandwiches, poutine, dumplings, schnitzel-wiches, Chinese crepes, and more.
11. Go for a trail run in Forest Park.
Get lost in the stunning maze of trails in Forest Park like the 30 miles of Wildwood Trail.
12. Revel in the Cathedral Park Jazz Festival.
This long-running free festival takes place under the inspiring arches of Cathedral Park beneath the St John’s Bridge.
13. See the swifts.
Every year in late summer thousands of Vaux Swifts gather near the same elementary school to roost during their fall migration. Just before dusk every night for a month, the birds swoop into a chimney for a spectacular display.
14. Cheer on the Adult Soapbox Derby.
Witness homemade wheeled vehicles barrel down the mountainside with their riders. Over 80 teams compete in this hilarious event every August. It’s free to watch.
15. Go on your own beer tour.
Find your favorite beer from the 58 breweries in the city. Get a taste of everything from the many taps at Horse Brass Pub, find a hidden European-style beer at The Commons Brewery, or try Cascade Brewing Barrel House for sour beer.
16. Discover a colorful mural in a hidden corner.
Every year since 2013 Forest For the Trees NW has sponsored local and international artists to paint the walls all over the city. In 2013-2014 alone artists created over 50 murals.
17. Get a cheese plate.
18. Play the classic arcades at Ground Kontrol.
This full-service bar showcases over 60 classic video games (like Joust, Street Fighter, Frogger, and of course, Pac-Man) and dozens of pinball machines. The whole family’s welcome until 5pm, then it’s adults-only.
19. Catch a show at Mississippi Studios.
Owned and run by musicians, this renovated church-turned-music-venue is the perfect place to catch some tunes.
20. Create a science experiment at adults-only OMSI After Dark.
Leave the kiddos at home and head to the science museum. Nibble on some local food and drink while you learn about robots, forensics, chemical concoctions, or just shoot off some water rockets.