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, 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 makes them exceptional. We went into the trip with a shortlist 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 and learn about the Shanghai Tunnels on a walking tour
3. Browse for books at Powell’s City of Books — the world’s largest bookstore
4. Wander amongst a whole world of rose species at Portland International Rose Test Garden or the Japanese Garden
5. Explore the way of the universe at the Oregon Museum of Science and Industry (OMSI)
6. Escape the city to Moulton Falls
7. Pass through for a few days on a Pacific Northwest road trip
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! Oregon is known for waterfalls, wooded forests, off-the-grid hot springs, and of course, the massive Crater Lake.
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
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
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 or experience all of the street food on a Portland street food tour
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
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
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 or go on a craft beer tasting tour
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
Love festivals? Discover more: 21 Weird + Unique World Festivals
Keeping Portland Weird
38. Experience everything peculiar at The Freakybuttrue 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 School, a former primary school. Even better, stay the night at McMenamins Edgefield for an eclectic and super fun evening! ($165+)
41. Wander the whimsical Hippo Hardware
42. Hang out at Sassy’s “Bar & Grill” (dare we say the most hipster strip club in the country?)
43. Spend the evening at Ground Kontrol and Quarterworld – Portland’s best barcades
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
Just Because
47. Try to find The Simpsons street names
48. Fly into the PDX airport and snap a photo of the famed 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.
Portland today, with kids, and at night.
The internet asked, so we’re answering. Here are a few more things to keep in mind for your trip.
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.
Unique Places to Stay in Portland
Looking to stay strange during your trip? Check out these local hotels in Portland:
Portland International Guest House | Just a walk away from Powell’s, the Portland Art Museum, and the Rose Test Garden you’ll find the no-frills Portland International Guesthouse. The accommodation falls somewhere between a hostel & a bed and breakfast, and is one of the best places for travelers looking to meet other travelers in Portland. Double rooms start from $96.
Travelers’ House | Located across the bridge near Portland’s alternative Alberta Arts District, the Travelers’ House is EXACTLY what it sounds like. It’s a house that has been updated to host travelers, but they’ve done a great job making it clean and cozy so it doesn’t feel the least bit like Couchsurfing. Double rooms start from $101.
McMenamin’s Kennedy School | On the edge of Portland, McMenamin’s Kennedy School offers one of the most unique overnights inside a revamped school building. Spend your evening drinking in library-themed bars or take a dip in the saltwater soaking pool. I promise this isn’t your average overnight! Double rooms start from €248.
The Ace Hotel | The Ace Hotel is a funky hotel chain with locations in New York City, Palm Springs, Seattle, Pittsburgh, Los Angeles, New Orleans, Chicago, London, Kyoto, and of course, Portand. Their Portland hotel is located in the former Clyde Hotel building just a block from the Pearl District. You’ll love the unconventional wall art and personalization that sets apart every room. Double rooms start from €320.
Airbnb | Portland is a quirky city full of quirky people living in quirky homes. To get the most local Portland experience, spend some time on Airbnb searching for unusual homes in neighborhoods where you’d like to stay. You can find everything from treehouses to tiny homes. New to Airbnb? Get $40 off your first stay or explore other properties from $50.
32 Comments
Colonel Buendia
May 26, 2016 at 3:24 pmI 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.
Sarah (JetSetting Fools)
May 27, 2016 at 1:44 pmFantastic list! I’ve been to Portland several times, but haven’t seen half of these! Saving this one for my upcoming trip 😉
Taylor Record
May 28, 2016 at 5:07 pmThanks 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!
Dalora Smith
July 18, 2016 at 3:26 pmGo 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.
Taylor Record
July 19, 2016 at 5:35 amWe had no idea the Tunnels had closed! Thanks for the update, Dalora. A ghost tour would make a great replacement, I’d say.
Paula W.
January 1, 2017 at 9:09 pmJust 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.
Carly
July 29, 2016 at 10:36 pmGo to Dante’s for sinferno night!!!
Taylor Record
July 31, 2016 at 6:59 amFire, burlesque, and aerial?? We’re totally in! Thanks for the rec, Carly!
dela nagle
September 28, 2016 at 10:07 amARE 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
Taylor Record
October 3, 2016 at 2:10 pmWe love San Francisco too, but hey! We figure there’s a city for everyone.
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, […]
Lizzy
January 16, 2017 at 4:44 pmYou 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.
Taylor Record
January 17, 2017 at 12:18 amThanks for the tip, Lizzy! Have you gotten to visit both? I think owning an unusual franchise like that would be a dream!
Lizzy Petitt
January 23, 2017 at 4:28 pmYes 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.
Gina
January 28, 2017 at 8:16 pmDid you happen to mean Multnomah Falls? Or was Yacolt WA and multon correct?
Taylor Record
February 11, 2017 at 1:58 amHey 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!
Nan
May 11, 2017 at 4:29 pmVisit 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.
Taylor Record
May 12, 2017 at 2:22 pmWe 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!
Erin
July 5, 2017 at 4:30 amI’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?
Taylor Record
July 5, 2017 at 9:00 amI did a bit of fact checking, and you’re right! Thanks for the tip, Erin!
Jason
June 24, 2017 at 5:56 amPretty good list!! My favorite thing in Portland was the fooooooodddd!!!!!
Taylor Record
June 24, 2017 at 2:47 pmMan, Portland does have some amazing food! Especially loved your recommendation for Luc Lac.
Melissa
July 17, 2017 at 9:43 pmSadly, 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.
Michelle
June 21, 2018 at 9:50 amGet “cupped up” at Cupping Studio in NE Portland’s Alberta Arts District – super cute Cupping Therapy Boutique (only costs $20 and is like a massage)
Greg
October 24, 2018 at 8:49 pmWas in Portland this weekend for VegFest 2018. Had some extra time so I rode the Max to
the Portland airport. Had lunch and took a carpet photo and texted to my family they all knew exactly where I was!
Taylor
October 25, 2018 at 5:28 pmProbably the only airport carpet in the world that doesn’t require an explanation. How was VegFest, Greg?
Greg
October 25, 2018 at 11:10 pmVegFest was great! Lots of valuable information from both doctors and animal rights activist on the benefits of a plant based diet for our health, the planet and of course the animals. I try to go every year. As I tell my wife – my weekend a year with several thousand of “my people” 🙂
Taylor
October 30, 2018 at 6:10 amHey, you found them! It can be so nice to find a group of people who get your lifestyle. Sounds super interesting.
Lacye
January 13, 2019 at 3:40 pmMoulton Falls Is not in Portland. That’s in Washington. Did you mean multnomah falls?
Taylor
January 13, 2019 at 5:02 pmI did mean Moulton Falls, Lacye! Pretty sweet that you can get over to Washington so fast.
Meet Saxena
April 17, 2019 at 9:36 amThis will come handy on my visit to Portland in the month of June. Thank you for sharing the to-do list.
Taylor
April 28, 2019 at 2:23 amYou bet. Hope you enjoy the trip!