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 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 and learn about the Shanghai Tunnels on a walking tour ($23)
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 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, wooded forests, and off-the-grid hot springs
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
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 ($59)
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
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 ($105)
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 ($15+) or Blazers Game
37. Participate or spectate the Naked Bike Ride
Keeping Portland Weird
38. Experience everything peculiar at The Freakybuttrue Peculiarium
39. Throw elbows at a Rose City Rollers women’s roller derby tournament
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
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.
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 quirky hotels in Portland:
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.
Caravan: The Tiny House Hotel | Caravan is the first tiny house hotel in the US (… whatever that means?) featuring six tiny houses on wheels. Each house is between 120-170 ft² with a kitchenette, private bathroom, and creative decor. Double rooms start from €180.
The Heathman Hotel | Not only was the Heathman built in the 1920’s, but anyone interested in the paranormal or movie tourism will have extra reason to stay the night. The hotel is known to be haunted in all of it’s rooms that finish up in “03” and you also might recognize it from its feature in 50 Shades of Grey. Double rooms start from €259.
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.
Traveling in the USA? Check out our other weird city guides:
- 101 weird + fun things to do in San Francisco
- 51 unique + fun things to do in Austin
- 51 unique + fun things to do in Birmingham
- OR Explore Tours in Portland on GetYourGuide
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