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51 weird + fun things to do in Portland | USA

Daniel on the PDX Carpet

It is absolutely as weird as you expect. Hidden coffee shops loom in unassuming backyards and you can hot tub at an elementary school turned bar and hotel. There are nickel arcades, primary schools turned hotels (booking.com), voodoo doll shaped donuts, a vaguely defined stop off the highway called “The Woodstock Mystery Hole”, and an almost endless list of fun things to do in Portland. As someone that is frequented by impractical  business ideas (milk your own milkshake bar!), I really do appreciate Portland’s follow through. Whoever dreamed up the Freakybuttrue Peculiarium, and actually stuck with it, is my entrepreneurial icon.

In Portland, even the most apparently boring experiences (here’s looking at you, Rose Garden) show a level of artistry and curation that make them exceptional. We went into the trip with a short list of weird things to in Portland, and came out with 51. You ready?

51 weird + fun things to do in Portland

Very Portland Experiences

1. Ride a bike, because literally everyone else is

2. Head underground into the Shanghai Tunnels

3. Browse for books at Powell’s City of Books — the world’s largest book store

4. Wander amongst a whole world of rose species at Portland International Rose Test Garden or the Japanese Garden

Bridge at Portland's Japanese Garden

5. Explore the way of the universe at Oregon Museum of Science and Industry (OMSI)

6. Escape the city to Moulton Falls

7. Take the tram to explore the city

8. Even better, see the whole city by the 4-T Trail (Trail, Tram, Trolley and Train)

9. Go thrifting in the Richmond

10. Get outside! An hour in any direction and you can be amongst waterfalls and wooded forests

Daniel checking out the view of Portland

11. See a show at the historic (formerly Vaudville) Aladdin Theater

12. Catch a one-of-a-kind event or show at Crystal Ballroom

13. Head to The Know for a punk show

14. Build bridges — or actually just cross them! Check out the views from Hawthorne Bridge and beyond

Taylor Record, traveloutlandish.com

15. Get your glow-in-the-dark putt putt on at Glowing Greens Putt Putt

Eating Portland

16. Scarf a Cap’n Crunch donut at Voodoo Doughnuts

Voodoo Doughnuts in Portland

17. Enjoy a more sophisticated donut at Blue Star

18. Go hungry to Pok Pok — they give you wings

19. Wander the Saturday Market

20. Grub at the food trucks (any food truck will do!)

Food Trucks in Portland

21. If Portland were an ice cream flavor, it would probably be Salt & Straw’s Stumptown Coffee & Burnside Bourbon. Eat it!

22. Settle in for a Portland brunch at Pine State Biscuits or Brunch Box

Brunch Box in Portland

23. Shop local produce at the farmer’s market

Drinking Portland

24. Like Bloody Marys? Brunch up and try a Tasty Mary or Dim Summore Mary at Tasty n Sons

Tasty n Sons Tasty Mary

25. Go spirit tasting along Distillery Row

26. Get going with a nitro coffee from Stumptown

27. Have a cup of coffee at the very-eclectic Rimsky-Korsakoffee

28. Play ping pong on the back patio of Rontoms

29. Drink a Portland craft beer

Craft Beer in Portland

30. Order a whiskey flight at Branch

31. Have happy hour at Departure for stellar city views

Events + Festivals in Portland

32. Visit during the First Thursday Art Walk

33. Time your visit around the Oregon Brewer’s Festival

34. Head to the woods for the indie and bluegrass Pickathon Independent Music Festival

35. Grub on Portland’s finest beers and bites at Feast Portland

36. Fan up at a Portland Timbers or Blazers Game

37. Participate or spectate the Naked Bike Ride

Keeping Portland Weird

38. Experience everything peculiar at The Freakybuttrue Peculiarium
Specimens in Portland's Peculiarium

39. Throw elbows at a Rose City Rollers women’s roller derby tournament

40. Soak in the tubs, drink, or catch a film at McMenamin’s Kennedy Schoola former primary school. Even better, stay the night at McMenamins Edgefield for an eclectic and super fun evening!

41. Wander the whimsical Hippo Hardware

42. Hang out at Sassy’s “Bar & Grill” (dare we say the hipsteriest strip club in the country?)

43. Spend the evening at Ground Kontrol and Quarterworld — Portland’s best barcades

Skeeball at the Nickel Arcades is definitely one of the most fun things to do in Portland

44. Seek out the Boeing 727 Airplane Home or email the owner to take a tour

45. Get off the highway at the Woodstock Mystery Hole (google it…)

46. Play pinball or other old school games at Electric Castle’s Wunderland + Avalon Theater nickel arcade

The Avalon Nickel Arcade in Portland

Just Because

47. Try to find The Simpsons street names

48. Fly to PDX airport and snap a photo of the famed PDX Carpet

Daniel on the PDX Carpet

49. Check out the world’s smallest park (it’s seriously small)

50. Tax-free shopping! We may or may not have bought a new computer in Portland, so you should take advantage too

51. Experience Portland on a rainy day (do you really want to move here, after all?)

BONUS: We’ve gotten a few excellent recommendations, but didn’t want to change the number! When in Portland, don’t forget to check out the Sloth Captive Husbandry Center, the Witch’s Castle in Forest Park, and the Portland City Grill for the best sunset views.

Cool Things to do in Portland Today: Check out what’s going on in Portland today and this weekend on the Travel Portland website!

Fun Things to do in Portland with kids: Plan the perfect day in Portland by starting your morning at the OMSI, taking the tram across the city, and finishing off with cheap games at the nickel arcade.

Unique Things to do in Portland at night: Start your evening at a Rose City Roller’s tournament or a Timber’s game, grab a craft beer, and get your booty over to Sassy’s.

Traveling in the USA? Check out our other weird city guides:

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Portland is just as weird as you expect. 51 weird + fun things to do in Portland

What are your favorite weird or cool things to do in Portland? Any suggestions we should add to the list?

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23 Comments

  • Reply
    Colonel Buendia
    May 26, 2016 at 3:24 pm

    I would add:
    (Powell Books probably deserves more than a single entry- after all you can browse for about the same amount of time of an entire literary era.)
    52. On a clear day taking Tri-Met up to Council Crest Park (1,000+ feet) and taking in Hood, Rainier, St. Helen’s, Adams, and Jefferson;
    53. A drink at the Heathman;
    54. A 10-mile drive and then a wander at Sauvie’s Island, pick berries, run a marathon;
    55. Take a ride on the Zoo Train.

  • Reply
    Sarah (JetSetting Fools)
    May 27, 2016 at 1:44 pm

    Fantastic list! I’ve been to Portland several times, but haven’t seen half of these! Saving this one for my upcoming trip 😉

    • Reply
      Taylor Record
      May 28, 2016 at 5:07 pm

      Thanks a lot, Sarah! Searching for “weird things to do in Portland” yielded more results than we could have hoped 😉 We hope you get to go back soon!

  • Reply
    Dalora Smith
    July 18, 2016 at 3:26 pm

    Go on a ghost tour! Or other walking tours with portland tours. I do not recommend the Shanghai haunted tour though. Also the shanghi tunnels are filled up. Our guide told us that no one can get into the Shanghai tunnels anymore.

    • Reply
      Taylor Record
      July 19, 2016 at 5:35 am

      We had no idea the Tunnels had closed! Thanks for the update, Dalora. A ghost tour would make a great replacement, I’d say.

      • Reply
        Paula W.
        January 1, 2017 at 9:09 pm

        Just an FYI, the shanghai tunnels have not closed; however you can only tour the city block beneath the entrance location. Road construction over the years have sealed the tunnels from adjacent city blocks, but the tour still describes the seedier side of portland by showing trapdoors and stories of kidnapping and slave labor.

  • Reply
    Carly
    July 29, 2016 at 10:36 pm

    Go to Dante’s for sinferno night!!!

    • Reply
      Taylor Record
      July 31, 2016 at 6:59 am

      Fire, burlesque, and aerial?? We’re totally in! Thanks for the rec, Carly!

  • Reply
    dela nagle
    September 28, 2016 at 10:07 am

    ARE YOU KIDDING? LAME!! The Golden Gate Bridge is 600 miles south, by this list San Francisco l
    ooks like it’s worth the 2 day drive. Geeeeeeze

    • Reply
      Taylor Record
      October 3, 2016 at 2:10 pm

      We love San Francisco too, but hey! We figure there’s a city for everyone.

  • Reply
    Things to do in Portland for First Timers | Two Scots Abroad
    October 10, 2016 at 7:58 am

    […] our family – Erin and Ian for letting us do a wash! I really did love this city, check out more cool things to do in Portland via our fellow blogger, […]

  • Reply
    Lizzy
    January 16, 2017 at 4:44 pm

    You can only go in the soaking pool at mcmenamins edgfield if you’re an overnight guest. Try the Kennedy school pool instead for day time admission.

    • Reply
      Taylor Record
      January 17, 2017 at 12:18 am

      Thanks for the tip, Lizzy! Have you gotten to visit both? I think owning an unusual franchise like that would be a dream!

      • Reply
        Lizzy Petitt
        January 23, 2017 at 4:28 pm

        Yes I’ve been to both. Edge field is cool because it’s such a huge property to explore and it has wine tasting as well, and a mini bar that is Greatful Dead themed. It’s super quirky. Kennedy school is actually an old school building with multiple restaurants/bars now, and a game room, movie theater and of course the soaking pool. You can spend the night too.

  • Reply
    Gina
    January 28, 2017 at 8:16 pm

    Did you happen to mean Multnomah Falls? Or was Yacolt WA and multon correct?

    • Reply
      Taylor Record
      February 11, 2017 at 1:58 am

      Hey Gina! That’s a good observation. We went to both, and thought Multon was a bit more relaxed and worth the visit. I could see how it would be confusing in a Portland post, though!

  • Reply
    Nan
    May 11, 2017 at 4:29 pm

    Visit Paxton Gate in the Old Mississippi part of the city for electric curiosities. Visit the Hawthorne district for all around “Local” shopping and don’t forget the Capital Grill happy hour, for the best view of the city at night.

    • Reply
      Taylor Record
      May 12, 2017 at 2:22 pm

      We forgot that there’s a Paxton Gate in Portland! The one in San Francisco is one of our favorite spots. We just added Capital Grill to the list. Thanks for the recommendation, Nan!

      • Reply
        Erin
        July 5, 2017 at 4:30 am

        I’ve lived in Portland for almost 30 years, and have never heard of a Capital Grill. The description makes me think you’re talking about Portland City Grill?

        • Reply
          Taylor Record
          July 5, 2017 at 9:00 am

          I did a bit of fact checking, and you’re right! Thanks for the tip, Erin!

  • Reply
    Jason
    June 24, 2017 at 5:56 am

    Pretty good list!! My favorite thing in Portland was the fooooooodddd!!!!!

    • Reply
      Taylor Record
      June 24, 2017 at 2:47 pm

      Man, Portland does have some amazing food! Especially loved your recommendation for Luc Lac.

  • Reply
    Melissa
    July 17, 2017 at 9:43 pm

    Sadly, Branch is no more. For other great spots like that in the area check out Wilder on 30th & Killingsworth or Bernie’s on Alberta & 29th.

    It’s also worth mentioning that Moulton Falls is up in Washington and more of a full afternoon trip. I agree that it’s totally worth it though.

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